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Issue 21, 2017
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Synthesis, properties, and crystal structures of π-extended double [6]helicenes: contorted multi-dimensional stacking lattice

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Abstract

The synthesis and properties of a new π-extended double [6]helicene 2 and a dithia[6]helicene 3 are described. Compared to the previously reported parent double-helicene molecule 1, the introduction of n-butyl groups successfully improved the solubility, which allowed an experimental investigation into the electronic structure of 2 and 3 by photophysical measurements and cyclic voltammetry. The characteristic two-blade propeller structures of 2 and 3 were unambiguously determined by single-crystal X-ray diffraction analysis. The crystal packing structure of 2 exhibited a contorted two-dimensional stacking, whereby molecules of n-pentane were incorporated in the stacks. Despite the presence of n-butyl groups, 3 formed a unique three-dimensional stacking lattice in the crystal. Time-resolved microwave conductivity measurements revealed that the double helicenes (1–3) exhibited transient conductivities. An organic field-effect transistor fabricated using 3 was found to function as a p-type transistor.

Graphical abstract: Synthesis, properties, and crystal structures of π-extended double [6]helicenes: contorted multi-dimensional stacking lattice

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Supplementary files

Article information


Submitted
22 Apr 2017
Accepted
12 May 2017
First published
12 May 2017

Org. Biomol. Chem., 2017,15, 4697-4703
Article type
Paper

Synthesis, properties, and crystal structures of π-extended double [6]helicenes: contorted multi-dimensional stacking lattice

T. Fujikawa, N. Mitoma, A. Wakamiya, A. Saeki, Y. Segawa and K. Itami, Org. Biomol. Chem., 2017, 15, 4697
DOI: 10.1039/C7OB00987A

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