Synthesis, Structure, and Chiroptical Properties of a Double [7]Heterohelicene

Wang XY, Wang XC, Narita A, Wagner M, Cao XY, Feng X, Muellen K (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 138

Pages Range: 12783-12786

Journal Issue: 39

DOI: 10.1021/jacs.6b08664

Abstract

The synthesis of 11a,25a-dibora-11,12,25,26-tetraoxatetranaphtho[1,2-a:2′,1′-f:1″,2″-j:2,1-o]perylene, a double [7]heterohelicene containing OBO units, has been achieved via tandem demethylation-borylation, representing the highest double helicene reported thus far with all six-membered rings. Single-crystal X-ray analysis clearly demonstrated a significantly twisted structure with the terminal aromatic rings overlapping at both ends, giving the first example of a double helicene with intramolecular π-layers. Such structural features resulted in a high theoretical isomerization barrier of 45.1 kcal/mol, which is the highest value for all the double helicenes ever reported, rendering the achieved molecule with high chiral stability. The (P,P)- and (M,M)-isomers were separated by chiral HPLC and the chiroptical properties were investigated, revealing opposite circular dichroism responses.

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:

Wang, X.-Y., Wang, X.-C., Narita, A., Wagner, M., Cao, X.-Y., Feng, X., & Muellen, K. (2016). Synthesis, Structure, and Chiroptical Properties of a Double [7]Heterohelicene. Journal of the American Chemical Society, 138(39), 12783-12786. https://doi.org/10.1021/jacs.6b08664

MLA:

Wang, Xiao-Ye, et al. "Synthesis, Structure, and Chiroptical Properties of a Double [7]Heterohelicene." Journal of the American Chemical Society 138.39 (2016): 12783-12786.

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