Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 16, Pages 5210-5213Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01674
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Funding
- Ministry of Education, Culture, Sports, Science & Technology in Japan (MEXT) [15H01004, 26288095]
- Japan Society for the Promotion of Science (JSPS) [PU14011]
- Grants-in-Aid for Scientific Research [16J02975, 26288095, 15H01004, 25248019] Funding Source: KAKEN
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Novel boron-fused double [5]helicenes were synthesized from hexabromobenzene in two steps via Hart reaction and demethylative cyclization. The parent helicene shows excellent ambipolar conductivity, which can be explained by unique 3D pi-stacking with a brickwork arrangement. Moreover, the introduction of four tert-butyl groups suppresses racemization, enabling optical resolution. The enantiomerically pure helicene shows deep blue fluorescence with Commission Internationale de l'Eclairage coordinates of (0.15, 0.08) and circularly polarized luminescence activity.
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