Development of highly fluorescent photochromic material with high fatigue resistance

被引：125

作者：

Jeong, Yong-Chul

Yang, Sung Ik ^{[1
]}

Kim, Eunkyoung

Ahn, Kwang-Hyun

机构：

[1] Kyung Hee Univ, Coll Environm & Appl Chem, Yongin 449701, South Korea

[2] Kyung Hee Univ, Coll Environm & Appl Chem, Yongin 449701, South Korea

[3] Kyung Hee Univ, Inst Nat Sci, Yongin 449701, South Korea

[4] Yonsei Univ, Dept Chem Engn, Seoul 120749, South Korea

来源：

TETRAHEDRON | 2006年 / 62卷 / 25期

基金：

新加坡国家研究基金会;

关键词：

photochromic reaction; diarylethene; fluorescence modulation; fatigue resistance;

D O I：

10.1016/j.tet.2006.04.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient and reversible fluorescence modulation with excellent photo-stability was achieved from a sulfone form of diacetyl diarylethene, 1,2-bis(6-acetyl-2-methyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (DABTFO4). The DABTFO4 emits strong fluorescence in the closed-ring isomer even in the absence of extra fluorophores. The fluorescence quantum yield, fatigue resistance, and photo-cyclization yield of DABTFO4 were significantly improved compared with the unsubstituted 1,2-bis(2-methyl-1-benzothiophene-1, 1-dioxide-3-yl)perfluorocyclopentene (BTFO4) and the sulfide analogue, 1,2-bis(6-acetyl-2-methyl-l-benzothiophene-3-yl)perfluorocyclopentene (DABTF6). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5855 / 5861

页数：7

共 34 条

[1] Poly(dithienylethene-alt-1,4-divinylenephenylene)s:: Increasing the molecular weights in diarylethene photochromic polymers
Bertarelli, C
Bianco, A
Boffa, V
Mirenda, M
Gallazzi, MC
Zerbi, G
[J]. ADVANCED FUNCTIONAL MATERIALS, 2004, 14 (11) : 1129 - 1133
[2] Highly fluorescent and photochromic diarylethene oligomer bridged by p-phenylenevinylene
Cho, H
Kim, E
[J]. MACROMOLECULES, 2002, 35 (23) : 8684 - 8687
[3] Fernández-Acebes A, 1999, CHEM-EUR J, V5, P3285, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3285::AID-CHEM3285>3.0.CO
[4] 2-Q
[5] Modulation of the absorption, fluorescence, and liquid-crystal properties of functionalised diarylethene derivatives
Frigoli, M
Mehl, GH
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (20) : 5243 - 5250
[6] Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level
Fukaminato, T
Sasaki, T
Kawai, T
Tamai, N
Irie, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) : 14843 - 14849
[7] Diheteroarylethenes as thermally stable photoswitchable acceptors in photochromic fluorescence resonance energy transfer (pcFRET)
Giordano, L
Jovin, TM
Irie, M
Jares-Erijman, EA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) : 7481 - 7489
[8] GREENE TW, 1999, PROTECTIVE GROUPS OR, P312
[9] THERMALLY IRREVERSIBLE PHOTOCHROMIC SYSTEMS - REVERSIBLE PHOTOCYCLIZATION OF 1,2-BIS(2-METHYLBENZO[B]THIOPHEN-3-YL)PERFLUOROCYCLOALKENE DERIVATIVES
HANAZAWA, M
SUMIYA, R
HORIKAWA, Y
IRIE, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) : 206 - 207
[10] Fatigue mechanism of photochromic 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene
Higashiguchi, K
Matsuda, K
Kobatake, S
Yamada, T
Kawai, T
Irie, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (10) : 2389 - 2394

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