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

Organic & Biomolecular Chemistry
Takao FujikawaKenichiro Itami

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.

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Citations

Feb 5, 2019·Angewandte Chemie·Maksim NavakouskiMarcin Stępień
Aug 14, 2019·Angewandte Chemie·Xiaoyu GuoJiaobing Wang
Jul 26, 2019·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
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Jan 26, 2021·Beilstein Journal of Organic Chemistry·Daria I TonkoglazovaOlga I Askalepova
Apr 4, 2020·Journal of the American Chemical Society·Nathaniel J SchusterColin Nuckolls
Feb 7, 2021·Angewandte Chemie· ChaolumenKenichiro Itami
Jul 22, 2021·Chemistry : a European Journal·Samuel Suárez-PantigaManuel Alcarazo
Jul 8, 2017·The Journal of Organic Chemistry·Takao FujikawaKenichiro Itami
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Nov 7, 2019·The Journal of Organic Chemistry·Maksim NavakouskiMarcin Stępień
Dec 16, 2021·Journal of the American Chemical Society·Maciej KrzeszewskiKenichiro Itami

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