TY - JOUR
T1 - Crystal Structures of Dimethoxyanthracens
T2 - A Clue to a Rational Design of Packing Structures of π-Conjugated Molecules
AU - Takimiya, Kazuo
AU - Ogaki, Takuya
AU - Wang, Chengyuan
AU - Kawabata, Kohsuke
N1 - Funding Information:
We gratefully acknowledge the Supercomputer System in the Advanced Center for Computing and Communication (ACCC) of RIKEN for support in theoretical calculations. We also thank the Center for Computational Materials Science, Institute for Materials Research, Tohoku University for the use of MASAMUNE‐IMR (MAterials science Supercomputing system for Advanced MUlti‐scale simulations towards NExt‐generation – Institute for Materials Research). This work was financially supported by JSPS KAKENHI Grant Number JP19H00906 and the Mitsubishi Foundation.
Funding Information:
We gratefully acknowledge the Supercomputer System in the Advanced Center for Computing and Communication (ACCC) of RIKEN for support in theoretical calculations. We also thank the Center for Computational Materials Science, Institute for Materials Research, Tohoku University for the use of MASAMUNE-IMR (MAterials science Supercomputing system for Advanced MUlti-scale simulations towards NExt-generation ? Institute for Materials Research). This work was financially supported by JSPS KAKENHI Grant Number JP19H00906 and the Mitsubishi Foundation.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/3/16
Y1 - 2020/3/16
N2 - 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.
AB - 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.
KW - crystal structures
KW - dimethoxyanthracenes
KW - intermolecular interactions
KW - rubrene-like pitched π-stacking
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U2 - 10.1002/asia.201901756
DO - 10.1002/asia.201901756
M3 - Article
C2 - 32022977
AN - SCOPUS:85080072057
SN - 1861-4728
VL - 15
SP - 915
EP - 919
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 6
ER -