Benzo-Fused Double [7]Carbohelicene: Synthesis, Structures, and Physicochemical Properties

Hu Y, Wang XY, Peng PX, Wang XC, Cao XY, Feng X, Muellen K, Narita A (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 56

Pages Range: 3374-3378

Journal Issue: 12

DOI: 10.1002/anie.201610434

Abstract

A benzo-fused double [7]carbohelicene (D7H) was synthesized through a regioselective cyclodehydrogenation of a tetranaphthyl-p-terphenyl-based precursor. The twisted (D7H-1) and anti-folded (D7H-2) conformers of D7H were separated by recrystallization, and their double helicene structures with overlapping terminal benzene rings were unambiguously elucidated by X-ray crystallography. A record-high isomerization barrier (46.0 kcal mol−1) in double helicenes was estimated based on density functional theory (DFT) calculation, which resulted in the excellent conformational stability of D7H. The physicochemical properties of D7H-1 and D7H-2 were investigated by UV/Vis absorption spectroscopy and cyclic voltammetry, displaying the variation of electronic structure upon conformational changes. The optical resolution of the racemic D7H-1 was carried out by chiral HPLC, offering enantiopure D7H-1-(P,P) and D7H-1-(M,M), which were further characterized by circular dichroism spectroscopy.

Involved external institutions

Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE) Xiamen University CN China (CN) Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Hu, Y., Wang, X.-Y., Peng, P.-X., Wang, X.-C., Cao, X.-Y., Feng, X.,... Narita, A. (2017). Benzo-Fused Double [7]Carbohelicene: Synthesis, Structures, and Physicochemical Properties. Angewandte Chemie International Edition, 56(12), 3374-3378. https://doi.org/10.1002/anie.201610434

MLA:

Hu, Yunbin, et al. "Benzo-Fused Double [7]Carbohelicene: Synthesis, Structures, and Physicochemical Properties." Angewandte Chemie International Edition 56.12 (2017): 3374-3378.

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