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Title: Structural Correlations and Percolation in Twisted Perylene Diimides Using a Simple Anisotropic Coarse-Grained Model

Abstract

Large, twisted, and fused conjugated molecular architectures have begun to appear more prominently in the organic semiconductor literature. From a modeling perspective, such structures present a challenge to conventional simulation techniques; atomistic resolutions are computationally inefficient, while traditional isotropic coarse-grained models do not capture the inherent anisotropies of the molecules. In this work, we develop a simple coarse-grained model that explicitly incorporates the anisotropy of these molecular architectures, thereby providing a route toward analyzing pi-stacking, and thus qualitative electronic structure, at a computationally efficient coarse-grained resolution. Our simple coarse-grained model maintains relative orientations of conjugated rings, as well as inter-ring dihedrals, that are critical for understanding electronic and excitonic transport in bulk systems. We apply this model to understand structural correlations in several recently synthesized perylene diimide (PDI)-based organic semiconductors. Twisted and nonplanar molecular architectures are found to promote amorphous morphologies while maintaining local pi-stacking. In conclusion, a graph theoretical network analysis demonstrates that these twisted molecules are more likely to form percolating three-dimensional pathways for charge motion than strictly planar molecules, which show connectivity in only one dimension.

Authors:
 [1]; ORCiD logo [2];  [1]; ORCiD logo [2]
+ Show Author Affiliations
  1. Univ. of Chicago, Chicago, IL (United States)
  2. Univ. of Chicago, Chicago, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division
OSTI Identifier:
1490087
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Chemical Theory and Computation
Additional Journal Information:
Journal Volume: 14; Journal Issue: 12; Journal ID: ISSN 1549-9618
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Bowen, Alec S., Jackson, Nicholas E., Reid, Daniel R., and de Pablo, Juan J. Structural Correlations and Percolation in Twisted Perylene Diimides Using a Simple Anisotropic Coarse-Grained Model. United States: N. p., 2018. Web. doi:10.1021/acs.jctc.8b00742.
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Bowen, Alec S., Jackson, Nicholas E., Reid, Daniel R., & de Pablo, Juan J. Structural Correlations and Percolation in Twisted Perylene Diimides Using a Simple Anisotropic Coarse-Grained Model. United States. https://doi.org/10.1021/acs.jctc.8b00742
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Bowen, Alec S., Jackson, Nicholas E., Reid, Daniel R., and de Pablo, Juan J. Thu . "Structural Correlations and Percolation in Twisted Perylene Diimides Using a Simple Anisotropic Coarse-Grained Model". United States. https://doi.org/10.1021/acs.jctc.8b00742. https://www.osti.gov/servlets/purl/1490087.
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@article{osti_1490087,
title = {Structural Correlations and Percolation in Twisted Perylene Diimides Using a Simple Anisotropic Coarse-Grained Model},
author = {Bowen, Alec S. and Jackson, Nicholas E. and Reid, Daniel R. and de Pablo, Juan J.},
abstractNote = {Large, twisted, and fused conjugated molecular architectures have begun to appear more prominently in the organic semiconductor literature. From a modeling perspective, such structures present a challenge to conventional simulation techniques; atomistic resolutions are computationally inefficient, while traditional isotropic coarse-grained models do not capture the inherent anisotropies of the molecules. In this work, we develop a simple coarse-grained model that explicitly incorporates the anisotropy of these molecular architectures, thereby providing a route toward analyzing pi-stacking, and thus qualitative electronic structure, at a computationally efficient coarse-grained resolution. Our simple coarse-grained model maintains relative orientations of conjugated rings, as well as inter-ring dihedrals, that are critical for understanding electronic and excitonic transport in bulk systems. We apply this model to understand structural correlations in several recently synthesized perylene diimide (PDI)-based organic semiconductors. Twisted and nonplanar molecular architectures are found to promote amorphous morphologies while maintaining local pi-stacking. In conclusion, a graph theoretical network analysis demonstrates that these twisted molecules are more likely to form percolating three-dimensional pathways for charge motion than strictly planar molecules, which show connectivity in only one dimension.},
doi = {10.1021/acs.jctc.8b00742},
journal = {Journal of Chemical Theory and Computation},
number = 12,
volume = 14,
place = {United States},
year = {Thu Nov 08 00:00:00 EST 2018},
month = {Thu Nov 08 00:00:00 EST 2018}
}
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https://doi.org/10.1021/acs.jctc.8b00742
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