Starburst Triarylamine Donor–Acceptor–Donor Quadrupolar Derivatives Based on Cyano‐Substituted Diphenylaminestyrylbenzene: Tunable Aggregation‐Induced Emission Colors and Large Two‐Photon Absorption Cross Sections

Abstract

In this work, we have developed a new class of aggregation-induced emission (AIE) active compounds, in which three electron-donating diphenylamine, phenothiazine, or carbazole groups are connected to the 1, 4-positions of the benzene through bis(α-cyano-4-diphenylaminostyryl) conjugation bridges to form three triarylamine quadrupolar derivatives (3 a-c). Their one- and two-photon absorption properties have been investigated. The two-photon absorption (2PA) cross sections measured by the open-aperture Z-scan technique were determined to be 1016, 1484, and 814 GM for 3 a-c, respectively. From this result, the high 2PA properties of these molecules are attributed to the extended π system and enhanced intramolecular charge transfer from the starburst triarylamine to the cyano group. Moreover, cyano-substituted diphenylamine styrylbenzene (CNDPASB)-based compounds are very weakly fluorescent in THF, but their intensities increase by almost 230, 70, and 5 times, respectively, in water/THF (v/v 90 %) mixtures, in which they exhibit strongly enhanced red, orange, and deep yellow fluorescence emissions, respectively. This result indicates that the intramolecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water, leading to significant increases in fluorescence. It was found that the color tuning of the CNDPASB-based compounds could be conveniently accomplished by changing the starburst triarylamine donor moiety. Multilayer electroluminescence devices with TPBI (2,2',2''-(benzene-1,3,5-triyl)-tri(1-phenyl-1H-benzimidazole)) electron-transporting layers have been made, with 3 a and 3 c as a non-doping red-yellow emitter. The preliminary results for these multilayer devices show a maximum efficiency of 0.25 %, and electroluminescence (EL) wavelengths around 568 nm. The excellent 2PA and AIE properties of these compounds make them potential materials for biophotonic applications.