Premium
Pyrene‐Containing Twistarene: Twelve Benzene Rings Fused in a Row
Author(s) -
Chen Wangqiao,
Li Xinxiong,
Long Guankui,
Li Yongxin,
Ganguly Rakesh,
Zhang Mingtao,
Aratani Naoki,
Yamada Hiroko,
Liu Ming,
Zhang Qichun
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808779
Subject(s) - pyrene , conjugated system , intermolecular force , molecule , benzene , crystallography , crystal structure , perpendicular , chemistry , materials science , chemical physics , organic chemistry , polymer , geometry , mathematics
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.