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Triarylamine groups have been widely utilized in the development of high-performance charge-transporting or luminescent materials for fabricating organic light-emitting diodes (OLEDs). In this study, atmospheric pressure chemical ionization (APCI) Q-Orbitrap mass spectrometry was adopted to investigate the dissociation behaviors of these triarylamine derivatives. Specifically, taking [M+H]+ as the precursor ion, high-energy collision dissociation (HCD) experiments within the energy range from 0 to 80 eV were carried out. The results showed that triarylamine derivatives with specific structures exhibited distinct fragmentation patterns. For diarylamine, the formation of odd-electron ions was ascribed to the single-electron transfer (SET) reaction mediated by ion-neutral complexes (INCs). In the low-energy range (below 40 eV), proton transfer served as the predominant mechanism for generating even-electron ions. Conversely, in the high-energy range (60 eV and above), the INC-SET reaction dominated. The precursor ion's structure affects compliance with the "even-electron rule", which has exceptions. Here, even-electron ion fragmentation was energy-dependent and could deviate from the rule, yet did not conflict with its concept, reflecting dissociation complexity. This research provides insights for triarylamine-based OLED materials, facilitating analysis and identification, and is expected to aid OLED material development. [ABSTRACT FROM AUTHOR]

Ir(III) complex phosphors with both ambipolar feature and aggregation-induced phosphorescence enhancement (AIPE) property are promising for furnishing high electroluminescent performance in solution-deposited phosphorescent organic light-emitting diodes. However, the molecular design is really challenging. To address this issue, we successfully designed and synthesized two ambipolar carbazole-based Ir(III) complexes Ir2CzNPO and Ir3CzNPO with AIPE behavior based on the N–P＝O resonant variation skeleton. Ir2CzNPO and Ir3CzNPO can exhibit high PLQYs of 0.76 and 0.98, respectively, in doped TCTA films. Furthermore, the PL intensity of Ir2CzNPO and Ir3CzNPO can be enhanced by around 6.1 and 3.7 folds, respectively, with the percentage of water volume increasing in the THF/water solvent system, indicating their AIPE behavior. The CV results demonstrate the ambipolar feature of Ir2CzNPO and Ir3CzNPO. Benefiting from the high PLQY, ambipolar feature and AIPE property, solution-deposited device B2 based on Ir3CzNPO can show a low turn-on voltage of 3.0 V and achieve a maximum external quantum efficiency (ηext) of 26.9%, a maximum current efficiency (ηL) of 69.2 cd A−1 and a maximum power efficiency (ηP) of 59.3 lm W−1. This research definitely paves a new and promising way for designing high-performance ambipolar phosphorescent materials with an AIPE feature for solution-deposited organic light-emitting diodes. [ABSTRACT FROM AUTHOR]

A simple and efficient method for the synthesis of diarylmethyl‐functionalized anilines through the hexafluoroisopropanol (HFIP)‐mediated regioselective 1,6‐hydroarylation reaction of para‐quinone methides (p‐QMs) with anilines under catalyst‐ and additive‐free conditions is reported. Various kinds of p‐QMs and amines (e. g. primary, secondary and tertiary amines) are well tolerated in this transformation without the pre‐protection of amino group, and the corresponding products could be generated with good to excellent yields and satisfactory regioselectivity under the optimized reaction conditions. In addition to adaptable amine compounds, indoles and their derivatives are also compatible with this reaction system. This transformation can be easily extended to a gram scale‐synthesis level to synthesize the target product. Furthermore, it is worth noting that some complex small aniline molecules with biological activity can be selectively modified using this method. The possible reaction mechanism is proposed through the step‐by‐step control experiments and DFT calculations, showing that the key process for achieving the regioselective 1,6‐hydroarylation of p‐QMs is the hydrogen bonding effect of HFIP to substrates. [ABSTRACT FROM AUTHOR]

A simple and efficient method for the synthesis of diarylmethyl-functionalized anilines through the hexafluoroisopropanol (HFIP)-mediated regioselective 1,6-hydroarylation reaction of para-quinone methides (p-QMs) with anilines under catalyst- and additive-free conditions is reported. Various kinds of p-QMs and amines (e. g. primary, secondary and tertiary amines) are well tolerated in this transformation without the pre-protection of amino group, and the corresponding products could be generated with good to excellent yields and satisfactory regioselectivity under the optimized reaction conditions. In addition to adaptable amine compounds, indoles and their derivatives are also compatible with this reaction system. This transformation can be easily extended to a gram scale-synthesis level to synthesize the target product. Furthermore, it is worth noting that some complex small aniline molecules with biological activity can be selectively modified using this method. The possible reaction mechanism is proposed through the step-by-step control experiments and DFT calculations, showing that the key process for achieving the regioselective 1,6-hydroarylation of p-QMs is the hydrogen bonding effect of HFIP to substrates., (© 2023 Wiley-VCH GmbH.)

A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)-OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)-OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials., (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)