Synthesis of Single and Double Dibenzohelicenes by Rhodium-Catalyzed Intramolecular [2+2+2] and [2+1+2+1] Cycloaddition

被引：49

作者：

Yamano, Ryota ^{[1
]}

Shibata, Yu ^{[1
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 24期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

anthracenes; cycloaddition; helical structures; luminescence; rhodium; CIRCULARLY-POLARIZED LUMINESCENCE; ONE HUNDRED YEARS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE SYNTHESES; PHOTOPHYSICAL PROPERTIES; HIGHLY FLUORESCENT; CRYSTAL-STRUCTURES; HELICENE; DICHROISM; COMPLEXES;

D O I：

10.1002/chem.201706008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dibenzo[7]helicenes were synthesized with up to 99% ee by rhodium(I)/binap-catalyzed enantioselective intramolecular [2+2+2] cycloaddition of 2-phenylnaphthalene-linked triynes. Additionally, [2+1+2+1] cycloaddition products, that is, twisted anthracenes, were also synthesized by using difluorphos as ligand. Although these compounds are not configurationally stable at elevated temperature, their Scholl reactions afforded configurationally stable double dibenzo[6]helicenes. The thus-obtained dibenzo[7]helicene exhibited good circularly polarized luminescence property and the double dibenzo[6]helicene showed high fluorescence quantum yield.

引用

页码：6364 / +

页数：7

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