TY - JOUR
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, De X.
AU - Xie, Nan
AU - Dang, Yi Z.
PY - 2005/6/24
Y1 - 2005/6/24
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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U2 - 10.1021/jo050236r
DO - 10.1021/jo050236r
M3 - Article
C2 - 15960498
AN - SCOPUS:20844434822
SN - 0022-3263
VL - 70
SP - 5001
EP - 5005
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -