Effects of Aromatic Stabilization Energies on Photochromism of New Asymmetrical Azaindole-Containing Diarylethenes

Three new asymmetrical diarylethenes containing an azaindole moiety and a variable heteroaryl ring have been synthesized. Their properties, such as photochromism, fatigue resistance, thermal stability, acidichromism, and fluorescence, were systematically investigated to elucidate the effects of arom...

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Bibliographic Details
Published in:Chinese journal of chemistry 2015-07, Vol.33 (7), p.785-791
Main Authors: Sun, Zhiyuan, Zhang, Congcong, Li, Hui, Fan, Congbin, Liu, Gang, Pu, Shouzhi
Format: Article
Language:English
Subjects:
acidichromism
aromatic stabilization energy
azaindole
diarylethene
fluorescence
photochromism
不对称
光致变色效应
吲哚化合物
氮杂
热稳定性
稳定能
耐疲劳性
芳香
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Summary:Three new asymmetrical diarylethenes containing an azaindole moiety and a variable heteroaryl ring have been synthesized. Their properties, such as photochromism, fatigue resistance, thermal stability, acidichromism, and fluorescence, were systematically investigated to elucidate the effects of aromatic stabilization energies （ASE） of the heteroaryl moieties. The results indicated that thermal stability decreased with the increment of the aromatic stabilization energies of the variable heteroaryl rings in the order of thiazyl〈thienyl〈pyrrolyl. Moreover, the dual switching behaviors of these azaindole-containing diarylethenes were also studied by the stimulation of acid/base and light. Addition of trifluoroacetie acid to the solutions of these diarylethenes resulted in obvious hypochromie shifts, and their N-protonated forms also exhibited favorable photochromism.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201500110