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Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′‐Bitriphenylene‐Based Sila[7]helicene
Author(s) -
Murayama Koichi,
Oike Yasuaki,
Furumi Seiichi,
Takeuchi Masayuki,
Noguchi Keiichi,
Tanaka Ken
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403565
Subject(s) - helicene , chemistry , racemization , enantioselective synthesis , cycloaddition , quantum yield , fluorescence , luminescence , yield (engineering) , crystallography , crystal structure , circular dichroism , stereochemistry , photochemistry , organic chemistry , molecule , optoelectronics , catalysis , optics , materials science , physics , metallurgy
A 1,1′‐bitriphenylene‐based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl‐linked tetrayne with a silicon‐linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X‐ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.