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Synthesis, characterization, and photochemical properties of chromophores containing photoresponsive azobenzene and stilbene
Author(s) -
Yang PoChih,
Wang YiHui,
Wu Hung
Publication year - 2011
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.35396
Subject(s) - azobenzene , photoisomerization , photochromism , diacetylene , photochemistry , chromophore , isomerization , chemistry , azo compound , polymer chemistry , materials science , polymer , organic chemistry , polymerization , catalysis
In this article, we describe the synthesis of two azobenzene and two stilbene‐based diacetylene chromophores containing terminal electron‐donating (OCH 3 ) and electron‐withdrawing (NO 2 ) terminal groups with esterification reactions. The target compounds were characterized by NMR, X‐ray diffraction (XRD), absorption, and photoluminescence spectroscopies. We investigated the structural effects of these photochromic compounds on the E–Z photoisomerization and 1,4‐addition under UV irradiation. 4‐[(4‐Nitrophenyl)‐diazenyl]phenyl pentacosa‐10,12‐diynoate, incorporating the electron‐withdrawing nitro group (NO 2 ), underwent the fastest rate of Z‐to‐E isomerization in darkness via a rotation mechanism. Our results demonstrate that self‐assembled azobenzene Z isomers exhibited enhanced fluorescence under UV irradiation. XRD spectroscopy identified bilayer packing by the polydiacetylene films after 1,4‐addition. Chromophores comprising the diacetylene group presented moderate photochromic stability upon 1,4‐addition, changing from their original yellowish color to form a blue phase. These synthesized compounds may be useful in the development of new and unique functional materials that exhibit bistable photochromism. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012