Development of highly fluorescent photochromic material with high fatigue resistance

Yong Chul Jeong; Sung Ik Yang; Eunkyoung Kim; Kwang Hyun Ahn

doi:10.1016/j.tet.2006.04.029

Development of highly fluorescent photochromic material with high fatigue resistance

Yong Chul Jeong, Sung Ik Yang, Eunkyoung Kim, Kwang Hyun Ahn

Department of Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

132 Citations (Scopus)

Abstract

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-1-benzothiophene-3-yl)perfluorocyclopentene (DABTF6).

Original language	English
Pages (from-to)	5855-5861
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2006.04.029
Publication status	Published - 2006 Jun 19

Bibliographical note

Funding Information:
This research was supported by Korea Research Foundation (KRF-2005-005-J00801) (K.H.A., S.I.Y.), and the Ministry of Science and Technology, Korea, through the Nanotechnology Development Program (E.K.).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.04.029

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title = "Development of highly fluorescent photochromic material with high fatigue resistance",

abstract = "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-1-benzothiophene-3-yl)perfluorocyclopentene (DABTF6).",

author = "Jeong, {Yong Chul} and Yang, {Sung Ik} and Eunkyoung Kim and Ahn, {Kwang Hyun}",

note = "Funding Information: This research was supported by Korea Research Foundation (KRF-2005-005-J00801) (K.H.A., S.I.Y.), and the Ministry of Science and Technology, Korea, through the Nanotechnology Development Program (E.K.).",

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AU - Jeong, Yong Chul

AU - Yang, Sung Ik

AU - Kim, Eunkyoung

AU - Ahn, Kwang Hyun

N1 - Funding Information: This research was supported by Korea Research Foundation (KRF-2005-005-J00801) (K.H.A., S.I.Y.), and the Ministry of Science and Technology, Korea, through the Nanotechnology Development Program (E.K.).

PY - 2006/6/19

Y1 - 2006/6/19

N2 - 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-1-benzothiophene-3-yl)perfluorocyclopentene (DABTF6).

AB - 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-1-benzothiophene-3-yl)perfluorocyclopentene (DABTF6).

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JO - Tetrahedron

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Development of highly fluorescent photochromic material with high fatigue resistance

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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