Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit

A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5- dihydropyrroles

Yi Chen, Dexing Zeng, Nan Xie, Yi Z. Dang

Research output: Contribution to journalArticle

132 Citations (Scopus)

Abstract

Symmetric and nonsymmetric diarylethenes with a 2,5-dihydropyrrole bridging unit have been prepared, and the photochromic properties are investigated. Both symmetric and nonsymmetric diarylethenes with 2,5-dihydropyrrole bridging units undergo reversible ring-opening and ring-closing photoisomerization reactions in nonpolar solvents with UV/vis light, and some of them exhibit good fatigue resistance and no marked degradation detected after 10 cycles via an on/off switch. In polar solvents, however, photochromic diarylethenes with 2,5-dihydropyrrole bridging units produce 3,4-diarylpyrrole derivatives instead of the ring-closing isomer of diarylethenes with UV light irradiation. A class of N-substituted 3,4-diphenylethenes with 2,5-dihydropyrrole bridging units were prepared and used as templates to investigate the conversion reactions. The mechanism of photoconversion of 3,4-diaryl-2,5-dihydropyrroles to 3,4-diarylpyrroles was explored as well.

Original languageEnglish (US)
Pages (from-to)5001-5005
Number of pages5
JournalJournal of Organic Chemistry
Volume70
Issue number13
DOIs
StatePublished - Jun 24 2005
Externally publishedYes

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Photochromism
Ultraviolet radiation
Photoisomerization
Isomers
Switches
pyrroline
Irradiation
Fatigue of materials
Derivatives
Degradation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit: A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5- dihydropyrroles",
abstract = "Symmetric and nonsymmetric diarylethenes with a 2,5-dihydropyrrole bridging unit have been prepared, and the photochromic properties are investigated. Both symmetric and nonsymmetric diarylethenes with 2,5-dihydropyrrole bridging units undergo reversible ring-opening and ring-closing photoisomerization reactions in nonpolar solvents with UV/vis light, and some of them exhibit good fatigue resistance and no marked degradation detected after 10 cycles via an on/off switch. In polar solvents, however, photochromic diarylethenes with 2,5-dihydropyrrole bridging units produce 3,4-diarylpyrrole derivatives instead of the ring-closing isomer of diarylethenes with UV light irradiation. A class of N-substituted 3,4-diphenylethenes with 2,5-dihydropyrrole bridging units were prepared and used as templates to investigate the conversion reactions. The mechanism of photoconversion of 3,4-diaryl-2,5-dihydropyrroles to 3,4-diarylpyrroles was explored as well.",
author = "Yi Chen and Dexing Zeng and Nan Xie and Dang, {Yi Z.}",
year = "2005",
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T1 - Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit

T2 - A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5- dihydropyrroles

AU - Chen, Yi

AU - Zeng, Dexing

AU - Xie, Nan

AU - Dang, Yi Z.

PY - 2005/6/24

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N2 - Symmetric and nonsymmetric diarylethenes with a 2,5-dihydropyrrole bridging unit have been prepared, and the photochromic properties are investigated. Both symmetric and nonsymmetric diarylethenes with 2,5-dihydropyrrole bridging units undergo reversible ring-opening and ring-closing photoisomerization reactions in nonpolar solvents with UV/vis light, and some of them exhibit good fatigue resistance and no marked degradation detected after 10 cycles via an on/off switch. In polar solvents, however, photochromic diarylethenes with 2,5-dihydropyrrole bridging units produce 3,4-diarylpyrrole derivatives instead of the ring-closing isomer of diarylethenes with UV light irradiation. A class of N-substituted 3,4-diphenylethenes with 2,5-dihydropyrrole bridging units were prepared and used as templates to investigate the conversion reactions. The mechanism of photoconversion of 3,4-diaryl-2,5-dihydropyrroles to 3,4-diarylpyrroles was explored as well.

AB - Symmetric and nonsymmetric diarylethenes with a 2,5-dihydropyrrole bridging unit have been prepared, and the photochromic properties are investigated. Both symmetric and nonsymmetric diarylethenes with 2,5-dihydropyrrole bridging units undergo reversible ring-opening and ring-closing photoisomerization reactions in nonpolar solvents with UV/vis light, and some of them exhibit good fatigue resistance and no marked degradation detected after 10 cycles via an on/off switch. In polar solvents, however, photochromic diarylethenes with 2,5-dihydropyrrole bridging units produce 3,4-diarylpyrrole derivatives instead of the ring-closing isomer of diarylethenes with UV light irradiation. A class of N-substituted 3,4-diphenylethenes with 2,5-dihydropyrrole bridging units were prepared and used as templates to investigate the conversion reactions. The mechanism of photoconversion of 3,4-diaryl-2,5-dihydropyrroles to 3,4-diarylpyrroles was explored as well.

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