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

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...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 48; no. 97; pp. 11838 - 11840
Main Authors Ogawa, Hatsune, Takagi, Kazuya, Ubukata, Takashi, Okamoto, Akiko, Yonezawa, Noriyuki, Delbaere, Stephanie, Yokoyama, Yasushi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2012
Royal Society of Chemistry
Subjects
Chemical Physics
Chemistry
Chemistry, Multidisciplinary
Constrictions
Conversion ratio
Cyclization
Exact solutions
Fixation
Hydrogen bonds
Indenes - chemical synthesis
Indenes - chemistry
Mathematical analysis
Molecular Conformation
Photochemical Processes
Photochromism
Physical Sciences
Physics
Science & Technology
Stereoisomerism
SUBSTITUENT
MEMORIES
DITHIENYLETHENE
CHIRAL HELICENOID DIARYLETHENE
REVERSIBLE DIASTEREOSELECTIVE PHOTOCYCLIZATION
ASYMMETRIC PHOTOCYCLIZATION
RING-CLOSURE
CYCLIZATION
BISBENZOTHIENYLETHENES
MOLECULES
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Summary: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.
Bibliography:KAKEN
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc35793c