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Regiocontrolled Dimerization of Asymmetric Diazaheptacene Derivatives Toward X-shaped Porous Semiconductors

Abstract

Conformationally rigid X-shaped PAHs are attracting interest due to their self-assembly into unique networks and as models to study through-space exciton and charge delocalization in one single molecule. We report here the synthesis of X-shaped PAHs by dimerization of diazaheptacene diimides. The diimide groups are employed to effectively direct the self-assembly into antiparallel dimer aggregates, which assist the compounds to undergo a regiocontrolled [4+4] dimerization, leading to X-shaped conformation bearing electron-poor and -rich subunits. The resulting PAHs are found to pack in 2D layers with large open channels and infinite π···π arrays. Furthermore, these high crystalline porous materials enable to serve as electron-transporting materials in OFET due to the long-range π-stacking arrays in the layers. This work presents a potentially generalizable strategy, which may provide a unique class of porous semiconductors for organic devices, taking advantage of their open channels.

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Article information


Submitted
08 Jul 2020
Accepted
15 Sep 2020
First published
16 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Regiocontrolled Dimerization of Asymmetric Diazaheptacene Derivatives Toward X-shaped Porous Semiconductors

G. Zhang , L. Zhang, A. Lv, X. Yang, Y. Zheng, W. Gu and N. Xue, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC03744C

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