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Org Lett. 2013 Jun 21;15(12):2938-41. doi: 10.1021/ol401012u. Epub 2013 Jun 7.

Photochromism of a naphthalene-bridged imidazole dimer constrained to the "anti" conformation.

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1
Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University , 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan, and CREST, Japan Science and Technology Agency (JST) , 7 Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan.

Abstract

Anti-1,8-bisTPI-naphthalene in which two imidazole rings are constrained to an anti-conformation leading to the first-formed 1,4'-isomer of the bridged imidazole dimer has been synthesized. The color of the radicals is different from that of the previously reported bridged-imidazolyl radicals because the intramolecular interaction between the radicals becomes weak due to the anti-conformation. This molecular design would be a profitable strategy to control the color of the radicals of the bridged imidazole dimer for application in ophthalmic lenses.

PMID:
23745651
DOI:
10.1021/ol401012u
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