Two-Step Synthesis of Boron-Fused Double Helicenes

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 π-stacking with a brickwork arrangement. Moreover, the introduct...

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Veröffentlicht in:Journal of the American Chemical Society 2016-04, Vol.138 (16), p.5210-5213
Hauptverfasser: Katayama, Takazumi, Nakatsuka, Soichiro, Hirai, Hiroki, Yasuda, Nobuhiro, Kumar, Jatish, Kawai, Tsuyoshi, Hatakeyama, Takuji
Format: Artikel
Sprache:eng
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Zusammenfassung: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 π-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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b01674