Characterization and photophysical properties of sulfur-oxidized diarylethenes

被引:32
作者
Jeong, Yong-Chul
Han, Jun Pil
Kim, Yongho
Kim, Eunkyoung
Yang, Sung Ik
Ahn, Kwang-Hyun
机构
[1] Yonsei Univ, Dept Chem Engn, Seoul 120749, South Korea
[2] Kyung Hee Univ, Coll Environm & Appl Chem, Yongin 449701, South Korea
[3] Kyung Hee Univ, MRCID, Yongin 449701, South Korea
关键词
photochromism; diarylethene; diastereoselective photocyclization; fatigue property; fluorescence readout; sulfoxide;
D O I
10.1016/j.tet.2007.02.007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Controlled oxidation of sulfur atoms in benzothiophene rings of a photochromic diarylethene, 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (BTF6) by 3-chloroperbenzoic acid afforded various oxidation products such as BTFO1, BTFO2, and BTFO4. Upon irradiation with UV light, colorless o-BTFO1 and o-BTFO2 turned to red color, whereas colorless o-BTFO4 turned to yellow color. Theoretical calculation was performed to understand the absorption spectra of closed-ring isomers. All of those compounds returned back to their open-ring isomers upon irradiation with visible light. The cyclization conversions of BTFOn (n= 1, 2, and 4) at the photostationary state are higher than that of BTF6. Interestingly, in the case of BTFO1, because of the unsymmetrical environment around the sulfoxide subunit in the molecule, the diastereoselective photocyclization was observed in 25% de. In addition, c-BTFO2 and c-BTFO4 also exhibited a marked fatigue resistance and strong fluorescence, respectively. Oxidation state of sulfur atom in a diarylethene can play an important role in determining its photophysical and photochromic properties. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3173 / 3182
页数:10
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