Synthesis and Property of Symmetrical Bispyridylthienylethenes Photochromic Compound

doi:10.11944/j.issn.1000-0518.2015.12.150147

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (12): 1431-1436.DOI: 10.11944/j.issn.1000-0518.2015.12.150147

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Synthesis and Property of Symmetrical Bispyridylthienylethenes Photochromic Compound

SUN Aibing,YU Chuanming,HU Bingcheng()

Institute of Chemical Engineering,Nanjing University of Science and Technology,Nanjing 210094,China

Received:2015-04-27 Accepted:2015-07-13 Published:2015-12-01 Online:2015-12-01
Contact: HU Bingcheng

Abstract

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

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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Synthesis and Property of Symmetrical Bispyridylthienylethenes Photochromic Compound

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