Jump to main content
Jump to site search

Issue 41, 2020
Previous Article Next Article

Regiocontrolled dimerization of asymmetric diazaheptacene derivatives toward X-shaped porous semiconductors

Author affiliations

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 an 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 highly crystalline porous materials serve as electron-transporting materials in OFETs due to the long-range π-stacked 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.

Graphical abstract: Regiocontrolled dimerization of asymmetric diazaheptacene derivatives toward X-shaped porous semiconductors

Back to tab navigation

Supplementary files

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., 2020,11, 11235-11243
Article type
Edge Article

Regiocontrolled dimerization of asymmetric diazaheptacene derivatives toward X-shaped porous semiconductors

G. Zhang, N. Xue, W. Gu, X. Yang, A. Lv, Y. Zheng and L. Zhang, Chem. Sci., 2020, 11, 11235
DOI: 10.1039/D0SC03744C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements