Ultimate diastereoselectivity in the ring closure of photochromic diarylethene possessing facial chirality
T Shiozawa, MK Hossain, T Ubukata… - Chemical …, 2010 - pubs.rsc.org
T Shiozawa, MK Hossain, T Ubukata, Y Yokoyama
Chemical communications, 2010•pubs.rsc.org… In fact, facial chirality has been successfully introduced to thermally reversible
photochromic azobenzenes. We report here on the use of this third chirality, ie, facial
chirality, on a diarylethene to induce 100% diastereoselectivity of photochromic ring closure
in various solvents, and the concept is shown in Scheme 1. If one of the two surfaces of an
aromatic ring (ring A) is occupied by a bulky attachment, ring closure is possible when the
other aromatic ring (ring B) approaches from the back of ring A. Perfect control of the …
photochromic azobenzenes. We report here on the use of this third chirality, ie, facial
chirality, on a diarylethene to induce 100% diastereoselectivity of photochromic ring closure
in various solvents, and the concept is shown in Scheme 1. If one of the two surfaces of an
aromatic ring (ring A) is occupied by a bulky attachment, ring closure is possible when the
other aromatic ring (ring B) approaches from the back of ring A. Perfect control of the …
A bisthienylethene with hitherto unprecedented facial chirality imposed by a triethyleneglycol bridge on a thiophene ring was synthesized and its photochromic ring closure was shown to occur with 100% diastereoselectivity upon UV-light irradiation.
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