Crystal Structures of Dimethoxyanthracens: A Clue to a Rational Design of Packing Structures of π-Conjugated Molecules
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Updated: Dec 29, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Kazuo Takimiya1,2, Takuya Ogaki2, Chengyuan Wang2
1Department of Chemistry Graduate School of Science, Tohoku University, 6-3 Aoba, Aramaki, Aoba-Ku, Sendai, Miyagi, 980-8578, Japan.
Abstract:
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.
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