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Crystal Structures of Dimethoxyanthracens: A Clue to a Rational Design of Packing Structures of π‐Conjugated Molecules
Author(s) -
Takimiya Kazuo,
Ogaki Takuya,
Wang Chengyuan,
Kawabata Kohsuke
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901756
Subject(s) - rubrene , intermolecular force , molecule , stack (abstract data type) , crystallography , crystal structure , conjugated system , solid state , materials science , chemistry , chemical physics , polymer , computer science , optoelectronics , organic chemistry , programming language
We carried out a systematic investigation of packing structures of a series of dimethoxyanthracenes, i. e., 1,4‐ ( 1 ), 1,8‐ ( 2 ), 1,5‐ ( 3 ), 2,6‐ ( 4 ), and 2,7‐derivatives ( 5 ). The packing structures of the dimethoxyanthracenes are classified into two types, a rubrene‐like pitched π‐stack ( 1 – 3 ) and a typical herringbone packing ( 4 and 5 ), which evidently show that the position of methoxy groups is crucial to determine the packing structure of dimethoxyanthracenes. Effects of the substitution position on intermolecular interactions are analyzed by the noncovalent intermolecular interaction (NCI) method, Hirshfeld surface analysis, and symmetry‐adapted perturbation theory (SAPT) method, thus clarifying active roles of the methoxy groups in the formation of rubrene‐like pitched π‐stack. The present results shed light on a molecular design strategy to realize the rubrene‐like pitched π‐stack in the solid state, which had been regarded as a packing structure limited for rubrene and its closely related derivatives.