Synthesis,Crystal Structure,and Photophysical Properties of (1E,3E,5E)‐1,3,4,6‐Tetraarylhexa‐1,3,5‐trienes: A New Class of Fluorophores Exhibiting Aggregation‐Induced Emission |
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Authors: | Masaki Shimizu Prof Dr Hironori Tatsumi Kenji Mochida Katsuhiro Shimono Dr Tamejiro Hiyama Prof Dr |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo‐ku, Kyoto 615‐8510 (Japan), Fax: (+81)?75‐383‐2445 http://npc05.kuic.kyoto‐u.ac.jp/e‐index.htm |
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Abstract: | Double Horner–Wadsworth–Emmons reaction of (E)‐2,3‐diaryl‐1,4‐bis(diethylphosphonyl)but‐2‐ene with (p‐substituted) benzaldehydes gave (1E,3E,5E)‐1,3,4,6‐tetraarylhexa‐1,3,5‐trienes in moderate to good yields. Substitution of electron‐withdrawing or ‐donating groups at the para position of the 1,6‐diphenyl groups induced a slight bathochromic shift of UV spectra measured in CHCl3 compared with that of the parent 1,3,4,6‐tetraphenylhexa‐1,3,5‐triene. Although fluorescence was not observed with all the trienes in CHCl3, they markedly emitted visible light in powder forms with quantum yields of 0.15–0.44. Introduction of amino groups at the para position of the 3,4‐diphenyl groups induced a bathochromic shift of emission maxima with good solid‐state quantum yields. Thus, the tetraarylated triene framework is found to serve as a new class of fluorophores that exhibit aggregation‐induced emission. |
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Keywords: | aggregation chromophores conjugation fluorescence materials science |
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