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2,2′-Bifuran-5,5′-dicarboxylic acid (BFDCA), a highly promising biobased diacid monomer, was used to modify poly(ethylene terephthalate) (PET) to obtain copolyesters with increased biocarbon conten...

Thieno­[2,3-c]­isoquinolin-5­(4H)-one is known for its potential as an anti-ischemic agent through the inhibition of poly­(ADP-ribose) polymerase 1 (PARP1). However, the compound also inhibits many other enzymes of the PARP family, potentially limiting its usability. The broad inhibition profile, on the other hand, indicates that this molecule backbone could be potentially used as a scaffold for the development of specific inhibitors for certain PARP enzymes. These efforts call for novel synthetic strategies for substituted thieno­[2,3-c]­isoquinolin-5­(4H)-one that could provide the needed selectivity. In this article, an efficient synthetic strategy for 8-alkoxythieno­[2,3-c]­isoquinolin-5­(4H)-ones through eight steps is presented and other tested synthetic pathways are discussed in detail. Synthesis of 7-methoxythieno­[2,3-c]­isoquinolin-5­(4H)-one is also demonstrated to show that the strategy can be applied widely in the syntheses of substituted alkoxythieno­[2,3-c]­isoquinolin-5­(4H)-ones.

The scaffold of TIQ-A, a previously known inhibitor of human poly-ADP-ribosyltransferase PARP1, was utilized to develop inhibitors against human mono-ADP-ribosyltransferases through structure-guided design and activity profiling. By supplementing the TIQ-A scaffold with small structural changes, based on a PARP10 inhibitor OUL35, selectivity changed from poly-ADP-ribosyltransferases towards mono-ADP-ribosyltransferases. Binding modes of analogs were experimentally verified by determining complex crystal structures with mono-ADP-ribosyltransferase PARP15 and with poly-ADP-ribosyltransferase TNKS2. The best analogs of the study achieved 10 – 20-fold selectivity towards mono-ADP-ribosyltransferases PARP10 and PARP15 while maintaining micromolar potencies. The work demonstrates a route to differentiate compound selectivity between mono- and poly-ribosyltransferases of the human ARTD family.

The room-temperature dissolution of cellulose in aqueous tetraethylammonium hydroxide (TEAOH) in the presence of carbamides (ureas) was investigated. Without carbamide, 35 wt% TEAOH was able to dissolve cellulose (microcrystalline cellulose) up to 3 wt%, whereas carbamides—such as urea, N-methylurea, N-ethylurea, 1,3-dimethylurea, and imidazolidone—were able to improve the dissolution of cellulose. At 5 wt% cellulose concentration, the highest carbamide contents in the solvent still able to dissolve cellulose within 1 h were 56 and 55 wt% of 1,3-dimethylurea and N-methylurea, respectively. When using urea, up to 15% of cellulose could be dissolved in a solution containing 22 wt% of urea. To demonstrate the possibility of the use of a carbamide-based solvent in cellulose modification, cationic cellulose was produced using glycidyltrimethylammonium chloride (GTAC). At a molar ratio of 1:3 of cellulose and GTAC, all the studied TEAOH–carbamide solvents produce cationic cellulose with higher charge density compared to the reference NaOH–urea solvent.

Two homopolyesters and a series of novel random copolyesters were synthesized from two bio-based diacid esters, dimethyl 2,5-furandicarboxylate, a well-known renewable monomer, and dimethyl 2,2′-bifuran-5,5′-dicarboxylate, a more uncommon diacid based on biochemical furfural. Compared to homopolyesters poly(butylene furanoate) (PBF) and poly(butylene bifuranoate) (PBBf), their random copolyesters differed dramatically in that their melting temperatures were either lowered significantly or they showed no crystallinity at all. However, the thermal stabilities of the homopolyesters and the copolyesters were comparable. Based on tensile tests from amorphous film specimens, it was concluded that the elastic moduli, tensile strengths, and elongation at break values for all copolyesters were similar as well, irrespective of the furan:bifuran molar ratio. Tensile moduli of approximately 2 GPa and tensile strengths up to 66 MPa were observed for amorphous film specimens prepared from the copolyesters. However, copolymerizing bifuran units into PBF allowed the glass transition temperature to be increased by increasing the amount of bifuran units. Besides enhancing the glass transition temperatures, the bifuran units also conferred the copolyesters with significant UV absorbance. This combined with the highly amorphous nature of the copolyesters allowed them to be melt-pressed into highly transparent films with very low ultraviolet light transmission. It was also found that furan–bifuran copolyesters could be as effective, or better, oxygen barrier materials as neat PBF or PBBf, which themselves were found superior to common barrier polyesters such as PET. acceptedVersion

Two renewable dicarboxylic acids, furan-2,5-dicarboxylic acid and 2,2′-bifuran-5,5′-dicarboxylic acid, were applied as bisphenol A substitutes to prepare partially bio-based dimethacrylate resins. The furan-based dimethacrylates were synthesized using their diglycidyl esters as intermediates, which were then reacted with methacrylic acid. This reaction was found to give isomeric mixtures, where the formed methacrylate end group had three different configurations as elucidated using one-dimensional (1D) and two-dimensional (2D) NMR. The ratio between the different end groups could be controlled to an extent by using 1,1,1,3,3,3-hexafluoroisopropanol as the sole reagent to facilitate a reaction between the furan diglycidyl esters and methacrylic acid. The control over the configuration of the methacrylate end group is demonstrated to be a possible tool to influence the properties of the resultant dimethacrylate monomer and the cured resin. The bifuran dimethacrylates were found to have viscosities of ca. 110–120 Pa·s at 25 °C, while the furan dimethacrylate had a viscosity of about 40 Pa·s at 25 °C. It is demonstrated that by diluting the furan-based dimethacrylates with 40 wt % of methacrylated eugenol, a bio-based reactive diluent, the liquid resins could be cured into thermosets with glass-transition temperatures of 177–209 °C and 5% mass loss temperatures of 359–375 °C under a nitrogen atmosphere. publishedVersion

The emulsification properties of carboxymethyl chitosan (CMChi) and hydrophobically modified carboxymethyl chitosan (h-CMChi) were studied as a function of pH and dodecane/water ratio. The pH was varied between 6-10, and the oil/water ratio between 0.1-2.0. In CMChi solution, the emulsion stability increased as the pH was lowered from 10 to 7, and the phase inversion was shifted from oil/water ratio 1.0 to 1.8, respectively. The system behaved differently in pH 6 due to the aggregation of CMChi and the formation of nanoparticles (∼200-300 nm). No phase inversion was observed and the maximum amount of emulsified oil was reached at oil/water ratio 1.2. The h-CMChi showed similar behavior as a function of pH but, due to hydrophobic modification, the phase inversion was shifted to higher values in pH 7-10. In pH 6, the behavior was similar, but the maximum amount of emulsified oil was higher compared to CMChi. The amount of adsorbed particles correlated with the emulsified amount of oil. Reversible emulsification of dodecane was demonstrated by pH adjustment using CMChi and h-CMChi solutions. The formed emulsions were gel-like, suggesting particle-particle interaction.

Spills due to the floating oil on the surface of sea water shows a significant alteration in the natural phenomenon of the marine ecosystem. Hence, amphiphilic sodium salt of oleoyl carboxymethyl chitosan (NaO-CMCS) was synthesized, characterized and studied as a sustainable adsorbent for the removal of floating oil in the oil spill treatment. Successful chemical modification of chitosan was confirmed by chemical analysis using Fourier Transform Infrared (FTIR), 1 H Nuclear Magnetic Resonance ( 1 H NMR), Scanning electron microscopy (SEM), Energy dispersive X-ray spectroscopy (EDS) and Elemental Analyzer. The effect of pH and salinity on the surface charge of NaO-CMCS was studied. Marine diesel was chosen as an oil phase for the emulsion studies. Hydrophobically modified NaO-CMCS shows the oil-in-water (o/w) emulsion stability for more than 6 weeks with droplet size ≤ 30 μm which increases with decreasing temperature. The behavior of emulsion with different salinity shows phase separation at pH 5, bridging flocculation at pH 6–7 and o/w emulsion at pH 8. Calcium ions act as a cross-linker between two carboxylic acid groups of NaO-CMCS, enhancing the removal of oil from the creamy emulsion. The recovery of oil was 75–85% and 19–49% from deionized water and sea water, respectively. Oil was not chemically altered during the recovery, demonstrating the effectiveness of this derivative in the oil spill response for the removal and recovery of floating oil from the sea water.

Oil spills are the significant sources of hydrocarbons entering in the receiving aquatic environment. An efficient method to remove hydrocarbons from water resources is adsorption. In this study, water soluble N,O-carboxymethyl chitosan (NO-CS) was synthesized by carboxymethylation of chitosan in a hydro-alcoholic medium at 50 °C by chloroacetic acid. The polymer was characterized through degree of deacetylation, degree of substitution, FTIR and 1 H NMR. Effectiveness of NO-CS as an adsorbent was studied as a function of dosage, salinity and pH to destabilize the Marine diesel (Oil-1), Diesel (Oil-2) and Marine-2T oil (Oil-3) into small oil droplets of less than 100 μm. Optical microscope was used for studying the size of oil droplets and adsorption effect of the oils on this polymer. The destabilization of marine diesel was the most effective among the studied three oils, which showed excellent adsorption at sea water alkalinity and salinity.

In environmental applications the applied materials are required to be non-toxic and biodegradable. Carboxymethyl chitosan nanoparticles cross-linked with Ca²⁺ ions (CMC-Ca) fulfill these requirements, and they are also renewable. These nanoparticles were applied to oil-spill treatment in our previous study and here we focused on enhancing their properties. It was found that while the divalent Ca²⁺ ions are crucial for the formation of the CMC-Ca, the attractive interaction between -NH₃⁺ and -COO⁻ groups contributed significantly to the formation and stability of the CMC-Ca. The stability decreased as a function of pH due to the deprotonation of the amino groups. Therefore, the nanoparticles were found to be fundamentally pH sensitive in solution, if the pH deviated from the pH (7–9) that was used in the synthesis of the nanoparticles. The pH sensitive CMC-Ca synthesized in pH 7 and 8 were most stable in the studied conditions and could find applications in oil-spill treatment or controlled-release of substances.

This study presents the use of a reactive deep eutectic solvent (DES) for the chemical modification of wood cellulose fibers. DES based on dimethylurea and ZnCl2 was used to synthetize cellulose methyl carbamate (CMeC). This synthesis was performed at elevated temperature under solvent-free conditions. Chemical characterization based on FTIR and NMR indicated that methyl carbamate was successfully introduced to cellulose, and a degree of substitution (DS) of 0.17 was obtained after 3 h of reaction at 150 °C. The product with a DS of 0.17 exhibited good alkaline solubility (in 3 % NaOH solution) after freeze-thawing, whereas the original cellulose fibers were practically insoluble even in 9 % NaOH. As dimethylurea can be produced from CO2, this method can be used as a sustainable way to obtain novel cellulose materials with desirable properties for use in a wide range of applications.

A direct coupling approach for the synthesis of 5,5′-bisfurfural via the coupling of 2-furaldehyde (furfural) and 5-bromo-2-furaldehyde using the air-stable catalyst Pd(OAc)2 and the air-stable ligand P(t-Bu)3HBF4 was examined. The developed procedure was used to functionalize thiophene containing moieties commonly found in organic electronics. The aromatic CH bond activated coupling with 5-bromo-2-furaldehyde afforded novel compounds with useful 5-heteroaryl-2-furaldehyde type functionality.

The benzothiadiazole moiety has been extensively exploited as a building block in the syntheses of efficient organic semiconducting materials during the past decade. In this paper, parallel synthetic routes to benzothiadiazole derivatives, inspired by previous computational findings, are reported. The results presented here show that various C-C cross-couplings of benzothiadiazole, thiophene, and thiazole derivatives can be efficiently performed by applying Xantphos as a ligand of the catalyst system. Moreover, improved and convenient methods to synthesize important chemical building blocks, e.g., 4,7-dibromo-2,1,3-benzothiadiazole, in good to quantitative yields are presented. Additionally, the feasibility of Suzuki-Miyaura and direct coupling methods are compared in the synthesis of target benzothiadiazole derivatives. The computational characterization of the prepared benzothiadiazole derivatives shows that these compounds have planar molecular backbones and the possibility of intramolecular charge transfer upon excitation. The experimental electrochemical and spectroscopic studies reveal that although the compounds have similar electronic and optical properties in solution, they behave differently in solid state due to the different alkyl side-group substitutions in the molecular backbone. These benzothiadiazole derivatives can be potentially used as building blocks in the construction of more advanced small molecule organic semiconductors with acceptor-donor-acceptor motifs.

Reinforcing, surface-functionalized cellulose nanocrystals (CNCs) with photoactive groups were obtained from wood cellulose fibers using sequential periodate oxidation and a “click-type” reaction between aldehyde groups and p-aminobenzoic acid in an aqueous environment, followed by mechanical disintegration. In the solution state, CNCs exhibited very high UV-absorption properties, especially in UVA and UVB regions (100% absorption was achieved with only 0.1% of CNCs) and high transparency in the visible light region (around 90% with 0.1% of CNCs). The fabricated CNCs functioned as lightweight-reinforcing fillers with high UV-absorption capability when incorporated into a poly(vinyl alcohol) (PVA) matrix. Complete UVA and UVB opacity of the nanocomposite was achieved using 10% of CNCs while simultaneously retaining over 80% transparency over the whole visible light spectrum. In addition, up to 33% and 77% higher tensile strength and modulus, respectively, were achieved using 10% of CNCs compared to pristine PVA. This result presented a unique way to produce multifunctional CNCs to be incorporated into nanocomposite structures instead of metal nanoparticles. These CNCs are supposed to be suitable for many applications requiring high visible light transparency and blocking of UV radiation.

Four aryl end-capped quaterthiophene derivatives were synthesized and their material properties were studied by computational, spectroscopic, electrochemical, and thermoanalytical methods. Compounds were applied as interfacial layers between the bulk heterojunction active layer and Ag anode in inverted organic solar cells. Results show that p-cyanophenyl end-capped quaterthiophene with hexyl side chains increases both the short circuit current density and power conversion efficiency notably compared to reference interlayer material, tris-(8-hydroxyquinoline)aluminum. The improved cell performance was attributed to the optimal positions of the highest occupied molecular orbital and the lowest unoccupied molecular orbital (LUMO) of this material, relative to those of the photoactive electron donor poly(3-hexylthiophene) and Ag anode, and evenly distributed LUMO. In addition, the use of these materials as an anode interfacial layer increases the absorption of the solar cell, which could contribute to the formation of excitons and additional current production by the cell.

A furan-based synthetic biopolymer composed of a bifuran monomer and ethylene glycol was synthesized through melt polycondensation, and the resulting polyester was found to have promising thermal and mechanical properties. The bifuran monomer, dimethyl 2,2′-bifuran-5,5′-dicarboxylate, was prepared using a palladium-catalyzed, phosphine ligand-free direct coupling protocol. A titanium-catalyzed polycondensation procedure was found effective at polymerizing the bifuran monomer with ethylene glycol. The prepared bifuran polyester exhibited several intriguing properties including high tensile modulus. In addition, the bifuran monomer furnished the polyester with a relatively high glass transition temperature. Films prepared from the new polyester also had excellent oxygen and water barrier properties, which were found to be superior to those of poly(ethylene terephthalate). Moreover, the novel polyester also has good ultraviolet radiation blocking properties. acceptedVersion

Efficient synthetic methods for carbazole-based small molecule electron donors with donor–acceptor (D–A) and A–D–A type structures were developed. In order to study the relation between chemical structures and material properties, the prepared compounds were characterized in detail using absorption spectroscopy, differential pulse voltammetry, and computational methods. In addition, symmetrical A–D–A type compounds were tested as an active layer component in bulk heterojunction based organic solar cell (OSC) devices with conventional structure. The results show that the two compound types have many similar properties. However, the extended molecular structure of A–D–A type compounds offer better film forming properties and higher molar absorption coefficients compared with the D–A type materials. Furthermore, the attachment of fluoro substituents in the A units has a positive effect on all solar cell device parameters. Moreover, the computational studies revealed that the molecular structures are twisted between the central carbazole D unit and π-bridge which may result in inefficient intramolecular charge transfer and, also, relatively limited short-circuit currents in OSC devices. acceptedVersion

A chemical pretreatment for producing cellulose nanocrystals (CNCs) with periodate oxidation and reductive amination is reported. This new functionalization of cellulose fibers dispenses an alternative method for fabricating individual CNCs without the widely used acid hydrolysis process. CNCs can be directly modified during the pretreatment step, and no additional post-treatments are required to tune the surface properties. Three butylamine isomers were tested to fabricate CNCs with amphiphilic features. After mechanical homogenization, CNCs occurred as individual crystallinities without aggregation where high uniformity in terms of shape and size was obtained. The elemental analysis and (1)H NMR measurement show that iso- and n-butylamine attach the highest number of butylamino groups to the cellulose fibers. Linking the alkyl groups increases the hydrophobic nature of the CNCs, where water contact angles from self-standing films up to 110.5° are reported. Since these butylamino-functionalized CNCs have hydrophobic characteristics in addition to the hydrophilic backbone of cellulose, the stabilization impact on oil/water emulsions is demonstrated as a potential application.

In this paper, we report the spectroscopic properties of a synthetically tailored Alq3 end-capped oligothiophene ((Alq3)2-OT) studied by steady state and time resolved spectroscopic methods in chloroform and solid films. In chloroform a photo-induced intramolecular electron transfer from the oligothiophene backbone to the Alq3 moiety was observed. When (Alq3)2-OT was mixed with a fullerene derivative (PCBM) in chloroform, we demonstrate that (Alq3)2-OT donates an electron to PCBM. With that in mind, (Alq3)2-OT was applied as a dopant molecule to improve the efficiency of P3HT:PCBM bulk hetero junction (BHJ) solar cells.

Tris(8-hydroxyquinoline)aluminum (Alq 3 ) is a frequently used material for organic light emitting diodes. The electronic properties and solubility can be tuned by chemical tailoring of the quinoline part, which makes it an interesting candidate for organic solar cells. Steady-state absorption and fluorescence, as well as time-resolved fluorescence properties of the parent Alq 3 and a series of complexes consisting of derivatives, such as 4-substituted pyrazol, methylpyrazol, arylvinyl, and pyridinoanthrene moieties, of the quinoline ligand, were studied in solutions and in thin films. Suitability of the complexes as anodic buffer layers or dopants in inverted organic solar cells based on the well known bulk heterojunction of poly(3-hexylthiophene) (P3HT) and phenyl-C 61 -butyric acid methyl ester (PCBM) was tested. The devices equipped with the derivatives showed higher power conversion efficiency ( η ) compared to the photocells containing the parent Alq 3 . Open circuit voltage ( V oc ) was increased when the derivatives were utilized as the anodic buffer layer. Doping of the P3HT:PCBM with a small amount of Alq 3 or its derivative improved short circuit current density, V oc , fill factor, and η , while the series resistance decreased. In addition, the devices were stable in air over several weeks without encapsulation. Possible mechanisms leading to the improvements in the photovoltaic performance by using the parent Alq 3 or its derivative as buffer layer or dopant are discussed.

A series of 4-substituted Alq 3 derivatives have been synthesized. Photophysical properties of the complexes in solution have been studied in detail. The results show that Hammett σ p constants of the substituents have a linear correlation with the emission maximum values of the aluminum complexes. Substitution at the 4-position improves the color purity of the emission and it has also a strong influence on the quantum yields. A new type of Alq 3 derivative, tris-(4-hydroxypyridinoanthrene)aluminum, has a good quantum yield and high emission color purity.

4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki–Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydrous Suzuki–Miyaura reaction conditions allows the use of commercially available but relative inert 5-chloro-8-hydroxyquinoline for the synthesis of 5-phenyl-8-hydroxyquinoline. Deprotection could easily be made by using suitable nucleophiles to afford the final 5-phenyl and 4-aryl-8-hydroxyquinolines in high yields. Under acidic conditions the tosyloxy group is sufficiently stable to allow selective further modification of acid labile functional groups.

Two different methods to graft silica particles with poly(acrylic acid) (PAA) were studied. In the first method PAA was reacted with 1,1′-carbonyldiimidazole to give functionalized PAA. The resulting activated carbonyl group reacted easily with 3-aminopropyl-functionalized silica at low temperatures. In the second method 3-glycidoxypropyl-functionalized silica particles were reacted directly with PAA by using magnesium chloride as a catalyst. Different molecular weights of PAAs were used in order to investigate the effect of molecular weight on grafting yields in both methods. The grafting yields were determined with thermogravimetric analysis (TGA). All products were also investigated with IR. The results showed that the yields of reactions performed at ambient temperature by using 1,1′-carbonyldiimidazole-functionalized PAA were the same as with a direct reaction of unfunctionalized PAA and 3-aminopropyl-functionalized silica performed at 153°C. Also in reactions between 3-glycidoxypropyl-functionalized silica and PAA the yields were satisfactory. Copyright © 2006 John Wiley & Sons, Ltd.

In this work, two p-cyanophenyl end-capped oligothiophenes, DPP-(2TPhCN)2 and di-(p-CNPh)4T, were compared as dopants in the P3HT:PC60BM bulk heterojunction (BHJ) layer of inverted organic solar cells. Inclusion of DPP-(2TPhCN)2 significantly increased the average efficiency of the solar cells, while the increase using di-(p-CNPh)4T doping in the cell efficiency was minor. In the BHJ photoactive layer, the dopant molecules are close to and interact with P3HT and PC60BM molecules. Intra- and intermolecular interactions of the dopant molecules with P3HT and PC60BM were studied in chloroform solutions. Energy or electron transfer from the dopant molecules to PC60BM takes place as the fluorescence emission intensity and lifetime of the dopant molecules decreased in the presence of PC60BM. In the case of doping with DPP-(2TPhCN)2, doped cells had higher absorbance than the non-doped reference cell and doping broadens the cell absorption to the near IR-region. Thus, the dopant molecules act as additional light absorbers in the photoactive layer and transfer energy or electrons to PC60BM, which increases the short circuit current and power conversion efficiency of the cell. Also, the emission of the cells doped with DPP-(2TPhCN)2 decreased when compared to that of the reference cell. In this case, P3HT can give electrons or energy to dopant molecules and the cell current and efficiency are further increased.

Six 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4-hydroxy-8-tosyloxyquinoline to give 4-chloro-8-tosyloxyquinoline in 94% yield. Treatment of the 4-chloro-8-tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4-amino and 4-thioalkyl-8-hydroxyquinolines in more than 70% yield. In case of sulphur nucleophiles and pyrrolidine, the removal of the protecting tosyl group at position 8 occurs simultaneously with the substitution of chlorine at position 4.

4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki–Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydrous Suzuki–Miyaura reaction conditions allows the use of commercially available but relative inert 5-chloro-8-hydroxyquinoline for the synthesis of 5-phenyl-8-hydroxyquinoline. Deprotection could easily be made by using suitable nucleophiles to afford the final 5-phenyl and 4-aryl-8-hydroxyquinolines in high yields. Under acidic conditions the tosyloxy group is sufficiently stable to allow selective further modification of acid labile functional groups.

Six 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4-hydroxy-8-tosyloxyquinoline to give 4-chloro-8-tosyloxyquinoline in 94% yield. Treatment of the 4-chloro-8-tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4-amino and 4-thioalkyl-8-hydroxyquinolines in more than 70% yield. In case of sulphur nucleophiles and pyrrolidine, the removal of the protecting tosyl group at position 8 occurs simultaneously with the substitution of chlorine at position 4.

Quinolines with a hydroxyl group at the 8-position and an alkoxy group at the 4-position are rare compounds. In this paper the synthesis of five 4-alkoxy-8-hydroxyquinolines is reported. The key reaction in the synthetic route is a selective protection of the hydroxyl group at C-atom 8 in 4,8-dihydroxyquinoline with a tosyl group and the hydrolytic removal of the protective group after the alkylation. The tosyl group is stable during the alkylations with various alkylating agents in the presence of sodium hydride.

Three new tetracyclic 8-hydroxyquinoline derivatives were synthesized by using a Pd catalyzed intramolecular direct arylation reaction in a key step. Furthermore, the new compounds were used as ligands in aluminium complexes and their photophysical properties were studied in detail both in solution and solid state by using absorption, steady-state, and time resolved fluorescence spectroscopies. Results show especially that the aluminium complex of 11H-indolo[3,2-c]quinolin-4-ol has the most blue-shifted emission maximum among the Alq3 derivatives to date and CIE chromaticity coordinates locate on the deep blue area (0.16, 0.12). Moreover, the fluorescence quantum yield of this compound is 3.1–3.5 times higher compared with the parent Alq3. Photophysical properties of the complex did not show major differences between the solution and the solid states. The lack of melting endotherm in DSC analysis indicates that the compound is amorphous. Based on the results, 11H-indolo[3,2-c]quinolin-4-ol has promising features to be applied as a ligand for aluminium or other metal ions in different applications.