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Comprehensive Summary: In recent years, there has been a shift towards using non‐fullerene electron acceptors in organic solar cells (OSCs) as a replacement for fullerene derivatives. This change requires polymer donors that possess compatible physical properties, such as absorption range, HOMO energy level, miscibility, and crystallinity. Moreover, the high cost and poor batch‐to‐batch reproducibility of polymer donors also hinder future large‐scale manufacturing. These emphasize the need to explore alternative types of polymer donors. The imide‐functionalized building units possess several key attributes that make their polymers highly promising for non‐fullerene OSCs. These attributes include ease of synthesis, strong electron‐withdrawing ability, rigid and co‐planar structure, and the ability to easily tune solubility through imide side chains. In this review, we summarized the synthetic routes of imide building units, and the structural evolution of imide‐functionalized polymer donors by focusing on the effects of polymer structure on their physical, optoelectronic, and photovoltaic properties. We hope that this mini‐review will serve as a catalyst for future research on imide‐functionalized polymers toward high‐performance, cost‐effective, and durable organic solar cells (OSCs). [ABSTRACT FROM AUTHOR]

Comprehensive Summary: In recent years, there has been a shift towards using non‐fullerene electron acceptors in organic solar cells (OSCs) as a replacement for fullerene derivatives. This change requires polymer donors that possess compatible physical properties, such as absorption range, HOMO energy level, miscibility, and crystallinity. Moreover, the high cost and poor batch‐to‐batch reproducibility of polymer donors also hinder future large‐scale manufacturing. These emphasize the need to explore alternative types of polymer donors. The imide‐functionalized building units possess several key attributes that make their polymers highly promising for non‐fullerene OSCs. These attributes include ease of synthesis, strong electron‐withdrawing ability, rigid and co‐planar structure, and the ability to easily tune solubility through imide side chains. In this review, we summarized the synthetic routes of imide building units, and the structural evolution of imide‐functionalized polymer donors by focusing on the effects of polymer structure on their physical, optoelectronic, and photovoltaic properties. We hope that this mini‐review will serve as a catalyst for future research on imide‐functionalized polymers toward high‐performance, cost‐effective, and durable organic solar cells (OSCs). [ABSTRACT FROM AUTHOR]

BACKGROUND: Faced with the need to develop new herbicides with modes of action different to those observed for existing agrochemicals, one of the most promising strategies employed by synthetic chemists involves the structural modification of molecules found in natural products. Molecules containing amides, imides, and epoxides as functional groups are prevalent in nature and find extensive application in synthesizing more intricate compounds due to their biological properties. In this context, this paper delineates the synthesis of N‐phenylnorbornenesuccinimide derivatives, conducts biological assays, and carries out in silico investigation of the protein target associated with the most potent compound in plant organisms. The phytotoxic effects of the synthesized compounds (2–29) were evaluated on Allium cepa, Bidens pilosa, Cucumis sativus, Sorghum bicolor, and Solanum lycopersicum. RESULTS: Reaction of endo‐bicyclo[2.2.1]hept‐5‐ene‐3a,7a‐dicarboxylic anhydride (1) with aromatic amines led to the N‐phenylnorbornenesuccinic acids (2–11) with yields ranging from 75% to 90%. Cyclization of compounds (2–11) in the presence of acetic anhydride and sodium acetate afforded N‐phenylnorbornenesuccinimides (12–20) with yields varying from 65% to 89%. Those imides were then subjected to epoxidation reaction to afford N‐phenylepoxynorbornanesuccimides (21–29) with yields from 60% to 90%. All compounds inhibited the growth of seedlings of the plants evaluated. Substance 23 was the most active against the plants tested, inhibiting 100% the growth of all species in all concentrations. Cyclophilin was found to be the enzymatic target of compound 23. CONCLUSION: These findings suggest that derivatives of N‐phenylnorbornenesuccinimide are promising compounds in the quest for more selective and stable agrochemicals. This perspective reinforces the significance of these derivatives as potential innovative herbicides and emphasizes the importance of further exploring their biological activity on weeds. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Two novel bio‐based benzoxazine monomers containing imide or amide group (HPIDD‐fa and HPBA‐fa) were synthesized from raw materials of benzoyl chloride/phthalic anhydride, tyramine, furfurylamine and paraformaldehyde via a two‐step reaction. Fourier transform infrared spectroscopy (FT‐IR), proton and carbon nuclear magnetic resonance (NMR) spectroscopies were performed to characterize the structures of the benzoxazine monomers. The curing behavior was investigated by using differential scanning calorimetry (DSC) and in situ FT‐IR, and the DSC results indicate that the peak curing temperatures of HPIDD‐fa and HPBA‐fa are centered at 248.5 and 230.1°C, respectively. In addition, thermogravimetric analysis (TGA) suggests that the newly developed bio‐based benzoxazine‐derived polybenzoxazines present excellent thermal stability with Td10 (temperature at 10% weight loss) of 385 and 368°C for poly(HPIDD‐fa) and poly(HPBA‐fa), respectively. The current investigation suggests that our newly obtained bio‐based thermosetting resins are promising materials for high‐tech applications. [ABSTRACT FROM AUTHOR]

Symmetrical aryl imides are synthesized from the reaction of activated amides such as N‐phenyl‐N‐tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3‐diketone mediates the generation of the N‐acyl donor from N,N‐bis(trimethylsilyl)amide. Various symmetrical aryl amides are thus formed in moderate to good yields. [ABSTRACT FROM AUTHOR]

Terminal aluminium and gallium imides of the type K[(NON)M(NR)], bearing heteroatom substituents at R, have been synthesised via reactions of anionic aluminium(I) and gallium(I) reagents with silyl and boryl azides (NON=4,5‐bis(2,6‐diisopropyl‐anilido)‐2,7‐di‐tert‐butyl‐9,9‐dimethyl‐xanthene). These systems vary significantly in their lability in solution: the N(SiiPr3) and N(Boryl) complexes are very labile, on account of the high basicity at nitrogen. Phenylsilylimido derivatives provide greater stabilization through the π‐acceptor capabilities of the SiR3 group. K[(NON)AlN(SitBuPh2)] offers a workable compromise between stability and solubility, and has been completely characterized by spectroscopic, analytical and crystallographic methods. The silylimide species examined feature minimal π‐bonding between the imide ligand and aluminium/gallium, with the HOMO and HOMO‐1 orbitals effectively comprising orthogonal lone pairs centred at N. Reactivity‐wise, both aluminium and gallium silylimides can act as viable sources of nitride, [N]3−, with systems derived from either metal reacting with CO to afford cyanide complexes. By contrast, only the gallium system K[(NON)Ga{N(SiPh3)}] is capable of effecting a similar transformation with N2O to yield azide, N3−, via formal oxide/nitride metathesis. The aluminium systems instead generate RN3 via transfer of the imide fragment [RN]2−. [ABSTRACT FROM AUTHOR]

Di‐ and multinuclear hafnium complexes bridged by ligands have been rarely reported. In this article, a novel 3,5‐disubstituted pyrazolate‐bridged ligand LH5 with two [N2N]2−‐type chelating side arms was designed and synthesized, which supported a series of dinuclear hafnium complexes. Dinuclear hafnium azides [LHf2(μ‐1,1‐N3)2(N3)2][Na(THF)4] 3 and [LHf2(μ‐1,1‐N3)2(N3)2][Na(2,2,2‐Kryptofix)] 4 were further synthesized and structurally characterized, featuring two sets of terminal and bridging azido ligands like jellyfishes. The reactivity of 3 under reduction conditions was conducted, leading to a formation of a tetranuclear hafnium imido complex [L1Hf2(μ1‐NH)(N3){μ2‐K}]25. DFT calculations revealed that the mixed imido azide 5 was generated via an intramolecular C−H insertion from a putative dinuclear HfIV‐nitridyl intermediate. [ABSTRACT FROM AUTHOR]

A new method for making use of the catalytic ending PdII-H for the relay-catalytic cycle for dicarbonylation of amines has been developed in a buffer condition, which shows an excellent compatible ability to allow two incompatible catalytic systems working simultaneously in the same catalytic system. [Display omitted] • A novel method for making use of the catalytic ending PdII-H into the next relay-catalytic cycle for dicarbonylation of amines in a buffer condition has been developed. • Two incompatible catalytic systems to work simultaneously in the same catalytic system. • This protocol features excellent regioselectivity and broad substrate scope. A new method for making use of the catalytic ending PdII-H for the relay-catalytic cycle for dicarbonylation of amines has been developed in a buffer condition, which shows an excellent compatible ability to allow two incompatible catalytic systems working simultaneously in the same catalytic system. This protocol features excellent regioselectivity and broad substrate scope. Our combined experimental and computational studies indicated that the reaction proceeds through a Pd0/PdII-H relay-catalytic cycle. [ABSTRACT FROM AUTHOR]

Oxidation is a prominent degradation route of biological molecules that produces a wide variety of degradation products through complex mechanisms and hence qualifies to be a vital pharmaceutical process. This article presents the kinetic and spectral study of the oxidation of an antimigraine drug rizatriptan benzoate (RTB) in an acid medium with the aid of a mild biocidal oxidant N-chloro-p-toluenesulfonamide, referred to as chloramine-T (CAT). The kinetic experimental studies reported here, such as fractional order dependency on RTB, pseudo-first-order dependency on CAT, negative fractional order dependency on the acid medium, independent of the rate on the ionic concentration and increasing rate with increasing dielectric constant, have led to the evaluation of stoichiometry, thermodynamic properties, and derivation of a rate equation. Effective interpretation of UV–Vis, IR, 1H and 13C NMR investigation was performed to identify and confirm the identity of the oxidation products and discuss the involved plausible mechanism. This study provides an extended insight into the products of oxidation formed during the metabolism of RTB.

The reactions of a terminal aluminium imide with a range of oxygen‐containing substrates have been probed with a view to developing its use as a novel main group transfer agent for the [NR]2− fragment. We demonstrate transfer of the imide moiety to [N2], [CO] and [Ph(H)C] units driven thermodynamically by Al−O bond formation. N2O reacts rapidly to generate the organoazide DippN3 (Dipp=2,6‐iPr2C6H3), while CO2 (under dilute reaction conditions) yields the corresponding isocyanate, DippNCO. Mechanistic studies, using both experimental and quantum chemical techniques, identify a carbamate complex K2[(NON)Al‐{κ2−(N,O)−N(Dipp)CO2}]2 (formed via [2+2] cycloaddition) as an intermediate in the formation of DippNCO, and also in an alternative reaction leading to the generation of the amino−dicarboxylate complex K2[(NON)Al{κ2−(O,O′)−(O2C)2N‐(Dipp)}] (via the take‐up of a second equivalent of CO2). In the case of benzaldehyde, a similar [2+2] cycloaddition process generates the metallacyclic hemi‐aminal complex, Kn[(NON)Al{κ2−(N,O)−(N(Dipp)C(Ph)(H)O}]n. Extrusion of the imine, PhC(H)NDipp, via cyclo‐reversion is disfavoured thermally, due to the high energy of the putative aluminium oxide co‐product, K2[(NON)Al(O)]2. However, addition of CO2 allows the imine to be released, driven by the formation of the thermodynamically more stable aluminium carbonate co‐product, K2[(NON)Al(κ2−(O,O′)−CO3)]2. [ABSTRACT FROM AUTHOR]

• Chloride modification accelerate electron injection. • Chloride modification position is critical for ion migration. • The dense and smooth film facilitate better electrochemical behavior. • Supercapacitor had high cycle stability, maintaining 78% after 10,000 cycles. Ambipolar conducting polymer electrode materials exhibit a wide voltage window, contributing to fast development of high-energy–density storage devices. The doping levels of p-doped and n-doped in ambipolar conducting polymers determine the electrochemical performance of energy storage devices. However, n-doped materials always face low doping efficiency, caused by difficulty in electron injection and ion migration, thereby affecting specific capacitance and stability. In this study, two ambipolar conductive polymers were developed, in which the n-doped imine group was chlorinated to improve electron injection, and the mechanism of ion migration process was studied by changing the chlorination of different positions relative to the carbonyl group. The influence of chloride modification on n-doped electrochemical energy storage was thoroughly investigated. The results show that chloride modification can lower the lowest unoccupied molecular orbital (LUMO) energy level of the monomer and make electron injection easier. Interestingly, the chloride modification position not only affects the oxidation–reduction of the carbonyl, but also the binding of the carbonyl with lithium ions. If the chloride modification position is too close to the carbonyl, lithium-ion migration in ambipolar conducting polymer will be restricted, although electron injection is beneficial. Based on this design, the developed PEPCl conducting polymer exhibits excellent electrochemical performance, and the mechanism of chlorination modification of ambipolar polymer electrode materials is described. [ABSTRACT FROM AUTHOR]

Cycloaliphatic epoxy resin exhibits excellent comprehensive properties suitable for application in electrical/electronic materials. However, its combustibility issue is more difficult to be handled in nature than aromatic epoxy resins and has not yet well addressed currently. The synergistic effect of multiple structures is the efficient way to solve this problem. Therefore, a novel cycloaliphatic epoxide monomer containing both imide and phosphate groups was designed via imidization and epoxidation in this study. The epoxide monomer BEMP with high purity was obtained by discussing the epoxidation conditions. Using 4-methyltetrahydrophthalic anhydride (MHHPA) as a hardener, the cured epoxy resin BMEP/MHHPA demonstrated inherently outstanding flame retardancy with a high limited oxygen index (LOI) value of 36.5% and achieved UL-94 V-0 rating. Additionally, BMEP/MHHPA showed a significant reduction of 70.5% in heat release rate (HRR) and 57.7% in total heat release (THR) compared to commercial ERL-4221/MHHPA. The synergistic effect of imide and phosphate groups contributed to strong charring ability and intumescent flame-retardant action, resulting in effectively isolating heat and oxygen, and inhibiting the production of volatile flammable components. This approach provides an efficient method for developing highly fire-safe cycloaliphatic epoxides for use in electrical/electronic applications. [Display omitted] • A cycloaliphatic epoxide monomer BMEP containing imide and phosphate groups was synthesized. • BMEP/MHHPA cured resins was hard to be ignited with an LOI value of 36.5%. • Heat release of BMEP/MHHPA was greatly reduced compared with commercial epoxy resins. • BMEP/MHHPA showed exceptional intumescent flame-retardant action. [ABSTRACT FROM AUTHOR]

The Mannich reaction under the action of secondary amines and paraformaldehyde in the presence of a CuCl catalyst was used to synthesize N-aminomethyl derivatives of methyl maleopimarimide ester. [ABSTRACT FROM AUTHOR]

Synthesis of Antiviral Compounds At the first stage, we successfully reproduced the scheme for the synthesis of the lead-compound B 2a b [[14]] and tried to modify the binding groups and their effect on the antiviral properties of obtained compounds (Scheme 1). Taking into account the propensity of the imide fragment to hydrolysis reactions, including in physiological media, we synthesized non-imide analogs of compound B 2a b and gave compound B 4 b as a potent ligand (first hit). In this regard, it should be concluded that in the course of the work carried out on the medicinal-chemistry modification of the lead-compound, two new, highly active compounds were identified that are superior in activity to compound B 2 b against the Coxsackievirus B3 Nancy. Keywords: enteroviruses; capsid binders; screening; imide; aminobenzoic acid; heterocycles EN enteroviruses capsid binders screening imide aminobenzoic acid heterocycles 1832 14 11/17/22 20221101 NES 221101 1. [Extracted from the article]

Herein, a three component Catellani‐type reaction catalyzed by the Palladium/Norbornene/CuI (Pd/NBE/CuI) cooperative system by using N‐acylph‐thalimides as acyl electrophiles is reported, which gives access to a series of aromatic ketones. The transformation is performable in the presence of water, albeit with decreased reaction yield. The additive CuI was crucial to facilitate the cleavage of C(O)−N bond of imide. This protocol showed broad substrate scope: both alkyl and aryl acyl groups could be installed at the ortho‐position of aryl iodides; alkenes and boronic acids can be used as termination reagents. [ABSTRACT FROM AUTHOR]

N-type organic semiconductors are of great importance for organic electronics. Nevertheless, the development of n-type organic semiconductors is far lagged than its counterpart of p-type organic semiconductors. Herein, a linear acenaphthene-imide-fused pyrazinacene-quinone (AIPQ) with high planarity is readily prepared via a two-fold condensation reaction. The incorporation of electron-withdrawing groups of imide, imine (C = N), and carbonyl (C = O) groups lowers the LUMO energy level of AIPQ to −4.12 eV, making it a promising candidate for n-type organic semiconductors. [ABSTRACT FROM AUTHOR]

The molecular design of a wide-bandgap polymer donor is critical to achieve high-performance organic photovoltaic devices. Herein, a new dibenzo-fused quinoxalineimide (BPQI) is successfully synthesized as an electron-deficient building block to construct donor–acceptor (D–A)-type polymers, namely P(BPQI-BDT) and P(BPQI-BDTT), using benzodithiophene and its derivative, which bears different side chains, as the copolymerization units. These two polymers are used as a donor, and the narrow bandgap (2,20-((2Z,20Z)-((12,13-bis(2-ethylhexyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo [3,4-e]thieno[2,″30′:4′,50]thieno[20,30:4,5]pyrrolo[3,2g]thieno[20,30:4,5]thieno[3,2-b]indole-2,10 diyl)bis(methanylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile) Y6 is used as an acceptor to fabricate bulk heterojunction polymer solar cell devices. Y6, as a non-fullerene receptor (NFA), has excellent electrochemical and optical properties, as well as a high efficiency of over 18%. The device, based on P(BPQI-BDTT):Y6, showed power conversion efficiencies (PCEs) of 6.31% with a JSC of 17.09 mA cm−2, an open-circuit voltage (VOC) of 0.82 V, and an FF of 44.78%. This study demonstrates that dibenzo-fused quinoxalineimide is a promising building block for developing wide-bandgap polymer donors. [ABSTRACT FROM AUTHOR]

Dual-ion electrochemical energy storage devices have attracted much attention due to their cost effectiveness and high operating voltage. Electrochemical properties such as the specific capacity of dual-ion energy storage devices are closely related to ion migration. However, the ion migration of dual-ion energy storage devices is slow, especially the cation migration, resulting in limited discharge capacity and poor rate performance. In this study, fluorinated and nonfluorinated ambipolar conductive polymers were prepared as electrode materials. The effects of fluorination on aggregation and solvent were studied as well as its role in improving ion migration. The results show that fluorination can increase the force of fluorination on the solvent, reduce the level of binding of the solvent to the ion, and regulate the aggregation state. Compared with the unfluorinated polymer of PEPOPE, the ion migration and electrochemical kinetics of PEPFEP were significantly improved, and the PEPFPE (71 F/cm 3 ) has a higher negative specific capacity than PEPOPE (24 F/cm 3 ) at a current density of 5 A/cm 3 .

An efficient method for the phosphine-catalyzed bisaddition of P(O)H compounds and cyclic imides to divinyl sulfone has been developed. The reaction proceeds under mild conditions and leads to the formation of the corresponding target products in high yield. The mono- and bisphosphonium salts have been obtained in high yield on the basis of divinyl sulfone. [ABSTRACT FROM AUTHOR]

Phytochemical profiling of the CH2Cl2 extract of the culture broth of a thermotolerant polyester-degrading actinomycete Actinomadura miaoliensis by a combination of column chromatography and preparative TLC afforded one new imide, called miaolimide (1). The structures were established by extensive spectroscopic analyses including 1D and 2D NMR (COSY, HSQC, and HMBC), and HR-ESI-MS, and by comparison with published data. [ABSTRACT FROM AUTHOR]

[Display omitted] • A series of imide-fused phenacenes were photochemically synthesized. • The imide-fused phenacenes showed apparent positive solvatofluorochromism due to their ICT characteristics. • Correlations between the Stokes shifts and conventional solvent polarity parameters revealed contribution form highly polar fluorescing state to the solvatofluorochromism. • An amino-substituted chrysene-imide produced red fluorescence with huge Stokes shift in toluene. • The present results provide a molecular design strategy of functionalized fluorophores utilizing phenacenes as the π platform. Chrysenes, picene, fulminene, modified with imide, bromo, and amino functionalities, were synthesized through Mallory photoreaction as the key step, and their electronic spectra were investigated. Fluorescence spectra of chrysene-diimide CHRDI and bromo-substituted phencanene-imides, BrCHRI , BrPICI , BrFULI were dependent on solvent polarity to display appreciable fluorescence color changes. The solvatofluorochromic behavior was analyzed by conventional relationships between Stokes shift and solvent polarity parameters, such as Lippert-Mataga and Bilot-Kawski equations. The results indicated that the solvatofluorochromism was derived from the intramolecular charge transfer (ICT) nature in the excited state. Theoretical studies using time-dependent density-functional theory revealed that the phenacene-imide molecules in the fluorescent state possessed ICT characters between the strongly electron-withdrawing imide moiety and moderately electron-donating phenacene cores. Amino-substituted chrysene-imide NH 2 CHRI showed fluorescence band in a red region (λ FL = 618 nm) in toluene with a very large Stokes shift (Δ ν ∼ = 7630 cm−1) suggesting that the molecule in the fluorescent state was highly polarized. The present results indicate that phenacenes would provide potential platforms for constructing future functional fluorophores through an appropriate functionalization. [ABSTRACT FROM AUTHOR]

The synthesis and structural characterization of the ferrocene imide derivatives Fc−CO−NH−CO−Me (4), Fc−CO−NH−CO−Fc (7) and Fc−CO−NH−CO−Fn−CO−NH−CO−Fc (8) have been reported. The mononuclear, dinuclear and trinuclear ferrocene imides were prepared by the reaction of ferrocenecarboxamide (3), with acetyl chloride, ferrocenecarbonyl chloride (2) and ferrocene-1,1’-(dicarbonyl chloride) (6), respectively. IR spectroscopic analysis revealed the absence of intramolecular hydrogen bonds in solutions of imides 4, 7 and 8. The crystal packing of N-acetylferrocenecarboxamide (4) is characterized by N−H⋯O hydrogen bonds forming centrosymmetric dimers, while the molecules of its homologue N-methylferrocenecarboxamide (5) are self-assembled by intermolecular N−H⋯O bonds into infinite chains. A detailed conformational analysis (DFT study) suggests the cis-trans configuration of ferrocene imide derivative 7 in solution. The effect of different substituents attached to bridged imide nitrogen on conformational properties of bis-ferrocenyl imides was further investigated and results compared to the existing experimental data.

A rhodium(III)‐based catalytic system has been used to develop a C−H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C−H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium‐catalyzed aldehydic C−H amidation. [ABSTRACT FROM AUTHOR]

A practical route is described for the preparation of α‐imido‐β‐diarylphosphorylpropanoates based on the phosphine‐catalyzed α‐umpolung/β‐Michael addition reaction. One of the products has been tested for coordination the Gd3+ cation using NMR relaxation method in solution and by IR spectroscopy to solids. The exact structures of two isomers of the obtained complex have been determined by single crystal analysis. The structures of all isomers were investigated by quantum‐chemical calculations in solution. Quantum‐chemical calculations results show the presence of stereoselective effect in solution: the trans‐isomer with two ligands having different chirality is energetically more favorable. The cis‐isomer with ligands of different chirality is the least advantageous in terms of energy and therefore presents in solution in small amounts. The cis‐ and trans‐isomers with two ligands of the same chirality are very close in energy but are somewhat inferior to the most stable isomer. [ABSTRACT FROM AUTHOR]

Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12 - A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC 50 values for compounds A12 - A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC 50 value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae , respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.

A series of novel 4-substituted sulfonamidobenzoic acid derivatives was synthesized as the structural evolution of 4-(4-(1,3-dioxoisoindolin-2-yl)phenylsulfonamido)benzoic acid, which is the known inhibitor of the enterovirus life cycle. Antiviral properties of prepared compounds were evaluated in vitro using phenotypic screening and viral yield reduction assay. Their capsid binding properties were verified in thermostability assay. We identified two new hit-compounds (4 and 7a) with high activity against the coxsackievirus B3 (Nancy, CVB3) strain with potencies (IC50 values of 4.29 and 4.22 μM, respectively) which are slightly superior to the reference compound 2a (IC50 5.54 μM). Both hits changed the heat inactivation of CVB3 in vitro to higher temperatures, suggesting that they are capsid binders, as 2a is. The results obtained can serve as a basis for further development of the lead compounds for novel drug design to combat enterovirus infection.

Wir berichten über die Synthese trigonaler Imidylcobaltkomplexe [Co(NAryl)L2]−, (L=N(Dipp)SiMe3, Dipp=2,6‐Diisopropylphenyl), mit sehr langen Co‐NAryl‐Bindungen von etwa 1.75 Å. Ihre elektronische Struktur wurde mit einer Vielzahl von physikalischen und spektroskopischen Methoden wie EPR oder Röntgenabsorptionsspektroskopie untersucht, was zu ihrer Beschreibung als höchst ungewöhnliche Imidylcobaltkomplexe führt. Computergestützte Analysen bestätigen diese Ergebnisse und zeigen weiter, dass der High‐Spin‐Zustand für den Imidylcharakter verantwortlich ist. Der Austausch des Dipp‐Substituenten am Imid durch die kleinere Mesitylfunktion (2,4,6‐Trimethylphenyl) bewirkt die unerwartete Me3Si‐Verschiebung vom Ligandenrückgrat zum Imidylstickstoff und offenbart einen hochreaktiven, nukleophilen Charakter der Imidyleinheit. [ABSTRACT FROM AUTHOR]

The molecular design of a wide-bandgap polymer donor is critical to achieve high-performance organic photovoltaic devices. Herein, a new dibenzo-fused quinoxalineimide (BPQI) is successfully synthesized as an electron-deficient building block to construct donor–acceptor (D–A)-type polymers, namely P(BPQI-BDT) and P(BPQI-BDTT), using benzodithiophene and its derivative, which bears different side chains, as the copolymerization units. These two polymers are used as a donor, and the narrow bandgap (2,20-((2Z,20Z)-((12,13-bis(2-ethylhexyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo [3,4-e]thieno[2,″30′:4′,50]thieno[20,30:4,5]pyrrolo[3,2g]thieno[20,30:4,5]thieno[3,2-b]indole-2,10 diyl)bis(methanylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile) Y6 is used as an acceptor to fabricate bulk heterojunction polymer solar cell devices. Y6, as a non-fullerene receptor (NFA), has excellent electrochemical and optical properties, as well as a high efficiency of over 18%. The device, based on P(BPQI-BDTT):Y6, showed power conversion efficiencies (PCEs) of 6.31% with a JSC of 17.09 mA cm−2, an open-circuit voltage (VOC) of 0.82 V, and an FF of 44.78%. This study demonstrates that dibenzo-fused quinoxalineimide is a promising building block for developing wide-bandgap polymer donors.

To develop highly heat‐resistant and flame‐retardant epoxy resins, the curing behavior of an epoxy resin and the properties of the resulting cured product were investigated using two compounds as curing agents, an acid anhydride containing a phenylethynylcarbonyl group and an imide compound with a phenylethynylcarbonyl group at both ends. The results indicated that reaction between the acid anhydride group and the epoxy group first proceeded at about 150°C to 170°C, followed by reaction between the phenylethynylcarbonyl groups at about 250°C to 300°C. The reaction between the acid anhydride and the epoxy group proceeded more efficiently in the presence of a small amount of the imide compound. The resulting product exhibited very good heat resistance and flame retardancy. The crosslink density was increased by polymerization of the phenylethynylcarbonyl group, and the resulting polyene structure and intramolecular imide skeleton strengthened intermolecular interactions, likely due to the limited freedom of movement of the molecular chains. [ABSTRACT FROM AUTHOR]

The title compounds, C19H12Br2N2O2 and C18H11Br2N3O2, were synthesized in good yields from condensation reactions of 3-bromo­benzoyl chloride with 2-amino­pyridine or 2-amino­pyrimidine using standard condensation reaction conditions and subsequent column chromatography. [ABSTRACT FROM AUTHOR]

Organic anode materials have attracted considerable interest owing to their high tunability by adopting various active functional groups. However, the interaction mechanisms between the alkali metals and the active functional groups in host materials have been rarely studied systematically. Here, a widely used organic semiconductor of perylene-3,4,9,10-tetracarboxylic diimide (PTCDI) was selected as a model system to investigate how alkali metals interact with imide functional groups and induce changes in chemical and electronic structures of PTCDI. The interaction at the alkali/PTCDI interface was probed by in-situ X-ray photoelectron spectroscopy (XPS), ultraviolet photoelectron spectroscopy (UPS), synchrotron-based near edge X-ray absorption fine structure (NEXAFS), and corroborated by density functional theory (DFT) calculations. Our results indicate that the alkali metal replaces the hydrogen atoms in the imide group and interact with the imide nitrogen of PTCDI. Electron transfer induced gap states and downward band-bending like effects are identified on the alkali-deposited PTCDI surface. It was found that Na shows a stronger electron transfer effect than Li. Such a model study of alkali insertion/intercalation in PTCDI gives insights for the exploration of the potential host materials for alkali storage applications. [ABSTRACT FROM AUTHOR]

Anionic molecular imide complexes of aluminium are accessible via a rational synthetic approach involving the reactions of organo azides with a potassium aluminyl reagent. In the case of K2[(NON)Al(NDipp)]2 (NON=4,5‐bis(2,6‐diisopropylanilido)‐2,7‐di‐tert‐butyl‐9,9‐dimethyl‐xanthene; Dipp=2,6‐diisopropylphenyl) structural characterization by X‐ray crystallography reveals a short Al−N distance, which is thought primarily to be due to the low coordinate nature of the nitrogen centre. The Al−N unit is highly polar, and capable of the activation of relatively inert chemical bonds, such as those found in dihydrogen and carbon monoxide. In the case of CO, uptake of two molecules of the substrate leads to C−C coupling and C≡O bond cleavage. Thermodynamically, this is driven, at least in part, by Al−O bond formation. Mechanistically, a combination of quantum chemical and experimental observations suggests that the reaction proceeds via exchange of the NR and O substituents through intermediates featuring an aluminium‐bound isocyanate fragment. [ABSTRACT FROM AUTHOR]

A continuous, scalable, and solvent‐free method for the synthesis of various naphthalic imides and perylene diimides (PDIs) using twin‐screw extrusion (TSE) is reported. Using TSE, naphthalic imides were obtained quantitatively without the need for excess amine reactant or product purification. With good functional‐group tolerance, alkyl and benzyl amine derived PDIs (incl. commercial dyes) were obtained in 50–99 % yield. Use of K2CO3, enabled synthesis of more difficult aniline‐derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day−1, corresponding to a space time yield of about 30×103 kg m−3 day−1, which is 1–2 orders of magnitude greater than for solvent‐based batch methods. These methods provide substantial waste reductions and improved efficiency compared to conventional solvent‐based methods. [ABSTRACT FROM AUTHOR]

An electrochemical four‐component reaction cascade Mumm rearrangement was developed. It is a rare example of in situ generation of O‐acyl isoamides for 1,3‐(O→N) acyl transfer. Inexpensive, commercially available arylethylenes, aryl or heterocyclic acids, acetonitrile, and alcohols were used as substrates. A wide range of aryl acids and alcohols were tolerated and provided imides in satisfactory yields. Subsequent hydrolysis of imides could be utilized to synthesize valuable amides and β‐amino alcohol derivatives. [ABSTRACT FROM AUTHOR]

Benzocyclobutene (BCB) resins have aroused much interest because of their excellent physical and chemical properties. Unfortunately the temperature required to induce cross-linking in typical BCBs is higher than 250°C, which restricts their applications. In this study, a novel cyano-containing BCB-terminated imide monomer was synthesized through the reaction of 1-cyano-5-amino-benzocyclobutene with 4,4′-oxydiphthalic anhydride. This monomer allows a 50–100°C lower curing temperature in comparison with typical BCBs, and it is highly soluble in various solvents and can easily convert to cured film at 150–200°C. Because of the presence of rigid imide group and strong polar cyano group, the cured film exhibits excellent mechanical strength with tensile strength up to 87.8 MPa, high glass transition temperature up to 350°C, low coefficient of thermal expansion (36.9 ppm K−1), and outstanding planarity with the average surface roughness as low as 0.26 nm. [ABSTRACT FROM AUTHOR]

Herein, we propose a new strategy to develop air-stable n-type organic semiconductors with non-classical thiophene aromatic diimide derivatives by replacing aromatic naphthalene with a heteroaromatic isothianaphthene core. We designed and successfully synthesized the isothianaphthene core based diimide material, N,N′-bis(n-hexyl)isothianaphthene-2,3,6,7-tetra-carboxylic acid diimide (BTDI-C6) as an n-type semiconductor. Compared to N,N′-bis(n-hexyl)naphthalene-1,4,5,8-tetracarboxylic acid diimide (NDI-C6), BTDI-C6 possesses a deeper LUMO energy level of −4.21 eV, which is 0.32 eV lower than that of NDI-C6. Both molecular modelling and experimental results elucidated that organic thin film transistors (OTFTs) based on both of these materials exhibit comparable mobilities; however, the threshold voltage of BTDI-C6 based device (+7.5 V) is significantly lower than that of NDI-C6 based counterpart (+34 V). Moreover, the low-lying LUMO energy level of BTDI-C6 ensures excellent air-stability which is further validated by the device performance. In addition, BTDI-C6 shows high luminescence while NDI-C6 is not luminescent at all in solution, which reveals the potential application of our newly synthesized material in n-type light-emitting transistors. [ABSTRACT FROM AUTHOR]

The reactivity of the yttrium trichloride complex [Cl 3 Y{(μ 3 -NH) 3 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)}] (2) with a variety of main-group metal cyclopentadienyl reagents [M(C 5 H 3 R1R2)] (M = Li, Na, K, Tl) or [Mg(C 5 H 5) 2 ] has been investigated. Treatment of 2 with one equivalent of [Na(C 5 H 5)] or [K(C 5 H 4 SiMe 3)] gives the monocyclopentadienyl derivatives [(η5-C 5 H 4 R)Cl 2 Y{(μ 3 -NH) 3 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)}] (R = H (3), SiMe 3 (4)). Analogous reaction of 2 with lithium [Li(C 5 H 3 R1R2)] or thallium [Tl(C 5 H 5)] reagents (1 or 2 equivalents) leads to complexes [(η5-C 5 H 3 R1R2) 2 Y(μ-Cl) 2 M{(μ 3 -NH) 3 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)}] (M = Li, R1 = R2 = H (5), R1 = H, R2 = SiMe 3 (6), R1 = R2 = SiMe 3 (7); M = Tl, R1 = R2 = H (8)). Complex 2 reacts with [Mg(C 5 H 5) 2 ] to yield the ionic compound [(μ-Cl) 3 Mg 2 {(μ 3 -NH) 3 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)} 2 ][{Y(η5-C 5 H 5) 2 Cl} 2 (μ-Cl)] (9). In contrast to the metathesis of chloride ligands, the reaction of 2 with the lithium indenyl derivative [Li(C 9 H 7)] at room temperature produces C 9 H 8 and the precipitation of [Li(μ-Cl) 3 Y{(μ 3 -N)(μ 3 -NH) 2 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)}] (10). Crystallization of 10 in pyridine affords the lithium-free [Cl 2 (py) 2 Y{(μ 3 -N)(μ 3 -NH) 2 Ti 3 (η5-C 5 Me 5) 3 (μ 3 -N)}] (11) complex. The X-ray crystal structures of 6 and 11 have been determined. Image 1 • Yttrium complexes with a tridentate imido-nitrido titanium metalloligand were synthesized. • Cyclopentadienyl derivatives were prepared by salt metathesis of chloride ligands bonded to yttrium. • Bis(cyclopentadienyl)magnesium gave a compound with a double-cube titanium-magnesium cation. • Indenyllithium led to deprotonation of a NH imido group and formation of a bridging nitrido ligand. [ABSTRACT FROM AUTHOR]

• One-pot synthesis of castor and tung oil-based polyurethane-imides was developed. • The introduction of Diels-Alder adducts notably increases the mechanical properties. • The thermal stability improves with the incorporation of imide groups. • The resulting polymers have high bio-renewable content. Herein, castor and tung oil-based polyurethane-imides with tailored thermal and mechanical performance were developed by a one-pot method. First, tung oil (TO) was transformed into eleostearic acid diethanol amide (EADEA) by methyl-esterification and amidation. The resulting EADEA was then mixed with castor oil (CO), N -(2-hydroxyethyl)-maleimide (HEMI) and isophorone diisocyanate to prepare biobased polyurethane-imides. The formation of Diels-Alder (DA) adducts from EADEA and HEMI during the curing process was determined by proton nuclear magnetic resonance (1H NMR) and Fourier transform infrared spectroscopy (FTIR). The effect of DA adducts contents on the thermal and mechanical properties of corresponding polymers was investigated. The results show that the introduction of TO-maleimide DA adducts significantly increases the glass transition temperature, tensile strength, Young's modulus and gel content of the resulting polyurethanes. The highest tensile strength of the resulting polymers can reach 48.2 MPa. Besides, the thermal stability was also improved with the incorporation of imide groups. This technique reported here demonstrates several advantages, such as one-pot synthesis, high bio-renewable content, low cost and tunable performance, and it is promising to find application in coatings, adhesives and so on. [ABSTRACT FROM AUTHOR]

Formally dianionic ligands such as alkylidenes or organoimidos play a major role in the organometallic chemistry of transition metals and are an emerging topical area of f‐element chemistry. The pursuit and development of main‐group‐metal congeners has been tackled sporadically but is clearly lacking behind. The pronounced ionic bonding in particular, prevailing in alkali and alkaline‐earth (Ae) metal derivatives, proved cumbersome. Recent substantial progress in the respective field of divalent Ae chemistry has been triggered by the implementation of new synthesis strategies involving new AeII precursors and tailor‐made ligands. The main emphasis of this Minireview will be on the synthesis and reactivity of well‐defined Group 2 alkylidenes, organoimides, silylenes, and phosphandiides. [ABSTRACT FROM AUTHOR]

Three five‐coordinate iron(IV) imide complexes have been synthesized and characterized. These novel structures have disparate spin states on the iron as a function of the R‐group attached to the imide, with alkyl groups leading to low‐spin diamagnetic (S=0) complexes and an aryl group leading to an intermediate‐spin (S=1) complex. The different spin states lead to significant differences in the bonding about the iron center as well as the spectroscopic properties of these complexes. Mössbauer spectroscopy confirmed that all three imide complexes are in the iron(IV) oxidation state. The combination of diamagnetism and 15N labeling allowed for the first 15N NMR resonance recorded on an iron imide. Multi‐reference calculations corroborate the experimental structural findings and suggest how the bonding is distinctly different on the imide ligand between the two spin states. [ABSTRACT FROM AUTHOR]

Ammonia is feeding nearly half the world population and also holds the promise as a carbon‐free energy carrier. The development of ammonia synthesis and decomposition processes under milder conditions is a grand challenge for more than a century. Increasing effort is devoted to this area in recent years and encouraging progress has been achieved. In this paper, we summarize our recent research using alkali or alkaline earth metal amides, imides and hydrides for ammonia synthesis and decomposition. These materials could serve as either indispensible component of active center in thermal catalytic process or nitrogen carrier for chemical looping ammonia synthesis. The synergy of amide, imide, or hydride with transition metals enables ammonia synthesis or decomposition with unprecedented high efficiency under milder reaction conditions, and thus opens an avenue to advance the chemistry or catalysis of N2 fixation reaction. The compositional and structural diversity of the amide, imide and hydride materials provides plenty of opportunity and potential for further exploration and optimization. [ABSTRACT FROM AUTHOR]

A novel variety of cycloaliphatic epoxy resins containing imide and diphenyl sulfone (named as 4,4′-bis[4-(4,5-epoxy-1,2,3,6-tetrahydro-phthalimido) phenoxy] diphenyl sulfone, BIES) is designed and synthesized through the three-step procedure. The mixtures of BIES and diglycidyl 4,5-epoxycyclohexane-1,2-dicarboxylate (TDE-85) are cured with methyl tetrahydrophthalic anhydride. Fourier transform infrared spectrum and proton nuclear magnetic resonance spectrum confirm that the BIES contains the chemical structure of imide and diphenyl sulfone. The measurements of glass transition temperature (Tg), heat distortion temperature (HDT), and the 5% weight loss temperature (T5%) show that the co-cured BIES/TDE-85 exhibits excellent heat resistance. For the BIES/TDE-85 with mass ratio of 0.2, Tg, HDT, and T5% of the co-cured epoxy are 175°C, 162°C, and 290°C, respectively. The impact strength increases from 117 J m−1 to 139 J m−1 with the increasing of the mass ratios of the BIES/TDE-85 from 0 to 0.2. [ABSTRACT FROM AUTHOR]

A novel thermosetting imide compound having a respective phenylethynyl carbonyl group at both terminal ends was newly synthesized from an acid anhydride having a phenylethynyl carbonyl group and various diamine compounds. The thermosetting behavior of the obtained novel thermosetting imide compound having phenylethynyl carbonyl groups was analyzed through differential scanning calorimetry measurements and infrared spectroscopic analysis. As a result, it became clear that a curing reaction of phenylethynyl carbonyl groups proceeds at approximately 200°C and that the curing reaction thereof proceeds at a temperature that is lower by 150°C or more compared with that of phenylethynyl groups. Examination of the polymerization reaction of the imide compounds having phenylethynyl carbonyl groups using model compounds revealed that a reaction that imparted an alkene C=C and polycyclic aromatic structure progressed. Moreover, a network polymer obtained from a thermosetting imide compound having respective phenylethynyl carbonyl groups at both terminal ends exhibited extremely superior heat resistance and thermal decomposition resistance. These superior thermal properties are thought to be due to the strong molecular interaction (molecular packing) that results from the polycyclic aromatic structures and alkenes produced through polymerization of the phenylethynyl carbonyl groups and to the suppression of the movement of the molecular chains. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • The synthesis of a series of cyclic imides of hydrazide benzenesulfonamides was reported. • The effect of an amide linker between the cyclic imide and the inhibitory scaffold was studied. • The derivatives were investigated as hCA I, II, IV and IX inhibitors. • The derivatives exhibited the best inhibitory activity against hCA II and hCA IX. • Of note, two interesting CA IV selected derivatives were found. Abstract The synthesis, characterization and biological evaluation of series of cyclic imides incorporating the 4-sulfamoylbenzamide scaffold (16 – 29) is disclosed. The compounds were designed by application of the "tail approach" to the aromatic sulfonamide scaffold and prepared by reacting the proper acid anhydride with 4-(hydrazinecarbonyl)benzenesulfonamide (15). Phtalimides and cyclic imides are biologically privileged scaffolds, endowed with versatile biological activity, such as an anti-proliferative action. The compounds were investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), and more specifically against the cytosolic hCA I and II and the transmembrane hCA IV and IX. Most screened sulfonamides exhibited great potency in inhibiting CA isoforms II, widely involved in glaucoma and other pathologies (K I s in the range of 0.7–62.3 nM), and IX, that is a validated anti-tumor target (K I s in the range of 3.0–50.9 nM), whereas interesting hydrophilicity-dependent inhibitory profiles were measured against isoform CA IV (K I s in the range of 3.9–428.6 nM). In silico studies were carried out to assess the binding mode of selected derivatives to hCA II, IV and IX. [ABSTRACT FROM AUTHOR]