Pyrene-Containing Twistarene: Twelve Benzene Rings Fused in a Row

Angewandte Chemie
Wangqiao ChenQichun Zhang

Abstract

Success in obtaining higher-order twistarenes with precise structures is very important for fundamentally understanding the relationship between the structures and physical properties/optoelectronic applications. In this research, by using the advantages from a retro-Diels-Alder process (clean reaction) and the cross-conjugated nature of the pyrene unit, a novel dodeca-twistarene was prepared for the first time. Its structure, confirmed by single-crystal XRD analysis, indicates that it possesses a twisted angle (≈30°), and two neighboring molecules in the crystal lattice are perpendicular to each other because of the twisted character and the strong intermolecular CH-π interactions. However, its basic physicochemical properties suggest its instability in air derives from its elevated HOMO energy level, although NICS calculations confirm that the pyrene units contribution poorly to the π conjugation of the overall molecule.

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Citations

Jan 3, 2019·Chemistry, an Asian Journal·Yongjun LiYuliang Li
Nov 19, 2019·Angewandte Chemie·Guogang LiuZhaohui Wang
Jan 17, 2020·ChemPlusChem·Marcus RichterXinliang Feng
Nov 11, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ben-Lin Hu, Qichun Zhang
Jan 19, 2021·Angewandte Chemie·Xuan YangMichael Mastalerz
Mar 18, 2021·The Journal of Organic Chemistry·Qi XuHua Jiang
Apr 21, 2021·Journal of the American Chemical Society·Rajeev K DubeyAurelio Mateo-Alonso
Jul 20, 2021·The Journal of Organic Chemistry·Xin DengJinchong Xiao
Jun 9, 2021·Chemistry : a European Journal·Andrej JančaříkAndré Gourdon
Jul 30, 2021·Accounts of Chemical Research·Gary J Richards, Jonathan P Hill
Sep 10, 2020·Journal of the American Chemical Society·Shuang MaJiaobing Wang
Feb 27, 2019·The Journal of Organic Chemistry·Yi HanYulan Chen
Nov 13, 2020·The Journal of Physical Chemistry. B·Yanbing HanYinglin Song
Feb 1, 2022·Journal of the American Chemical Society·Rajeev K DubeyAurelio Mateo-Alonso

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