噻唑并噻唑荧光团表现出强荧光和类似紫精的可逆电致变色作用,Journal of the American Chemical Society

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噻唑并噻唑荧光团表现出强荧光和类似紫精的可逆电致变色作用
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-05-08 00:00:00 , DOI: 10.1021/jacs.7b01005
Alexis N. Woodward ₁ , Justin M. Kolesar ₁ , Sara R. Hall ₁ , Nemah-Allah Saleh ₁ , Daniel S. Jones ₁ , Michael G. Walter ₁

Affiliation

报道了N，N′-二烷基化和N，N′-二苄基化二吡啶鎓噻唑并[5，4- d ]噻唑衍生物的合成，电化学和光物理特性。噻唑并噻唑紫精显示出强烈的蓝色荧光，且量子产率高，介于0.8-0.96之间。二辛基，二甲基和二苄基衍生物在低还原电势下也显示出独特且可逆的黄色至深蓝色电致变色。稠合的双环噻唑并[5,4-d]噻唑杂环使烷基化吡啶鎓基团保持平面，强烈影响其电化学性能。单线量子产率大大与外围4-吡啶基团的季铵化增强（Φ _˚F从0.22增至0.96），而长寿命荧光寿命则在1.8-2.4 ns之间。使用循环伏安法，紫外可见吸收度和荧光光谱，光谱电化学和时间分辨光致发光对噻唑并噻唑紫精进行了表征。的电致变色特性在溶液中观察到，除了他们的强的荧光发射特性，这可根据图2e被抑制^-减少，使这些材料为多官能光电，电子传递感测和其他光化学应用具有吸引力。

"点击查看英文标题和摘要"

Thiazolothiazole Fluorophores Exhibiting Strong Fluorescence and Viologen-Like Reversible Electrochromism

The synthesis, electrochemical, and photophysical characterization of N,N′-dialkylated and N,N′-dibenzylated dipyridinium thiazolo[5,4-d]thiazole derivatives are reported. The thiazolothiazole viologens exhibit strong blue fluorescence with high quantum yields between 0.8–0.96. The dioctyl, dimethyl, and dibenzyl derivatives also show distinctive and reversible yellow to dark blue electrochromism at low reduction potentials. The fused bicyclic thiazolo[5,4-d]thiazole heterocycle allows the alkylated pyridinium groups to remain planar, strongly affecting their electrochemical properties. The singlet quantum yield is greatly enhanced with quaternarization of the peripheral 4-pyridyl groups (Φ_F increases from 0.22 to 0.96) while long-lived fluorescence lifetimes were observed between 1.8–2.4 ns. The thiazolothiazole viologens have been characterized using cyclic voltammetry, UV–visible absorbance and fluorescence spectroscopy, spectroelectrochemistry, and time-resolved photoluminescence. The electrochromic properties observed in solution, in addition to their strong fluorescent emission properties, which can be suppressed upon 2 e^– reduction, make these materials attractive for multifunctional optoelectronic, electron transfer sensing, and other photochemical applications.

更新日期：2017-06-28

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