Characterization and photophysical properties of sulfur-oxidized diarylethenes

Yong Chul Jeong, Jun Pil Han, Yongho Kim, Eunkyoung Kim, Sung Ik Yang, Kwang Hyun Ahn

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3173-3182
Number of pages10
JournalTetrahedron
Volume63
Issue number15
DOIs
Publication statusPublished - 2007 Apr 9

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sulfoxide
Sulfur
Color
Isomers
Oxidation
Cyclization
Ultraviolet Rays
Irradiation
Fatigue
Atoms
Fluorescence
Light
Ultraviolet radiation
Absorption spectra
Fatigue of materials
Molecules
benzothiophene
perfluorocyclopentene
3-chloroperbenzoic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Jeong, Yong Chul ; Han, Jun Pil ; Kim, Yongho ; Kim, Eunkyoung ; Yang, Sung Ik ; Ahn, Kwang Hyun. / Characterization and photophysical properties of sulfur-oxidized diarylethenes. In: Tetrahedron. 2007 ; Vol. 63, No. 15. pp. 3173-3182.
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Characterization and photophysical properties of sulfur-oxidized diarylethenes. / Jeong, Yong Chul; Han, Jun Pil; Kim, Yongho; Kim, Eunkyoung; Yang, Sung Ik; Ahn, Kwang Hyun.

In: Tetrahedron, Vol. 63, No. 15, 09.04.2007, p. 3173-3182.

Research output: Contribution to journalArticle

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