Issue 97, 2012
From the journal:

Chemical Communications

Bisarylindenols: fixation of conformation leads to exceptional properties of photochromism based on 6π-electrocyclization†

Hatsune Ogawa,a   Kazuya Takagi,a   Takashi Ubukata,a   Akiko Okamoto,b   Noriyuki Yonezawa,b   Stephanie Delbaerec  and  Yasushi Yokoyama*a  

* Corresponding authors

a Graduate School of Engineering, Yokohama National University, Tokiwadai, Yokohama 240-8501, Hodogaya, Japan
E-mail: yyokoyam@ynu.ac.jp
Fax: +81 45-339-3934
Tel: +81 45-339-3934

b Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, Koganei 184-8588, Naka-machi, Japan
E-mail: yonezawa@cc.tuat.ac.jp

c Université Lille Nord de France, UDSL, UMR CNRS 8516, BP83, Lille, France
E-mail: stephanie.delbaere@univ-lille2.fr

Abstract

Thermally irreversible photochromic 1-tert-butyl-substituted 2,3-bisthiazolylindenol has been synthesized. It showed perfect diastereoselectivity and high ring-closing quantum yield with high conversion ratio to the closed form. The collaborative interaction of two intramolecular hydrogen bonds and the steric restriction fixed the conformation in favour of cyclization in a highly diastereoselective manner.

Graphical abstract: Bisarylindenols: fixation of conformation leads to exceptional properties of photochromism based on 6π-electrocyclization

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Article information

DOI
https://doi.org/10.1039/C2CC35793C
Article type
Communication
Submitted
10 Aug 2012
Accepted
06 Sep 2012
First published
07 Sep 2012

Chem. Commun., 2012,48, 11838-11840

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Bisarylindenols: fixation of conformation leads to exceptional properties of photochromism based on 6π-electrocyclization

H. Ogawa, K. Takagi, T. Ubukata, A. Okamoto, N. Yonezawa, S. Delbaere and Y. Yokoyama, Chem. Commun., 2012, 48, 11838 DOI: 10.1039/C2CC35793C

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