对称吡啶基二噻吩乙烯光致变色化合物的合成与性能

doi:10.11944/j.issn.1000-0518.2015.12.150147

摘要/Abstract

摘要：

二噻吩乙烯光致变色化合物具有热稳定性高、抗疲劳性好等优点。本文以2-甲基噻吩为原料,经过Suzuki偶联、傅克酰基化、McMurry环合3步反应制备1,2-二(5-吡啶基-2-甲基噻吩-3-基)环戊烯,总收率61%。所有中间体及目标产物均已通过核磁共振、质谱、红外光谱等技术手段表征。该合成方法具有合成步骤少、简便、总收率高、易于工业化生产等优点。利用紫外-可见吸收光谱、荧光光谱对该化合物及其与镍离子、锡离子相互作用的光致变色性能以及应用进行了研究。对称吡啶基二噻吩乙烯通过与金属配位在紫外光的照射前后显示出不同的颜色和光谱吸收,可以用作新型金属离子探针。

关键词: 光致变色, 二芳基乙烯, 吡啶, 探针

Abstract:

Photochromic bisthienylethene has advantages of thermal-stability and fatigue-resistance. This paper reported a new 3-stage synthesis of 1,2-bis(5-pyridyl-2-methylthien-3-yl)cyclopentene in 61% total yield via Suzuki coupling, Friedel-Crafts acylation and McMurry coupling by using 2-methylthiophene as the starting material. The intermediates and the target compound were confirmed by ¹H NMR, ¹³C NMR, MS and IR. This synthetic method is concise, high yielding and easy for scaling up. Photochromic properties of the target compound and its interaction with Ni²⁺, Sn²⁺ were also investigated by UV-Vis spectroscopy and fluorescent emission spectroscopy. Symmetrical 1,2-bis(5-pyridyl-2-methylthien-3-yl)cyclopentene displayed different colors and UV-Vis spectra by coordinated with metal ions. The response to ions allowed the material to be used as a new kind of probe for metal ions.

Key words: photochromism, diarylethene, pyridine, probe

孙爱兵, 余传明, 胡炳成. 对称吡啶基二噻吩乙烯光致变色化合物的合成与性能[J]. 应用化学, 2015, 32(12): 1431-1436.

SUN Aibing, YU Chuanming, HU Bingcheng. Synthesis and Property of Symmetrical Bispyridylthienylethenes Photochromic Compound[J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1431-1436.

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