We report on the control of π-stacking modes (herringbone vs slipped-stack) and photophysical properties of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA), an anthracene-based organic semiconductor (OSC), by isosteric cocrystallization (i.e., the replacement of one functional group in a coformer with another of “similar” electronic structure) with 2,4,6-trihalophenols (3X-ph-OH, where X = Cl, Br, and I). Specifically, BP4VA organizes as slipped-stacks when cocrystallized with 3Cl-ph-OH and 3Br-ph-OH, while cocrystallization with 3I-ph-OH results in a herringbone mode. The photoluminescence and molecular frontier orbital energy levels of BP4VA were effectively modulated by the presence of 3X-ph-OH through cocrystallization. We envisage that the cocrystallization of OSCs with minimal changes in cocrystal formers can provide access to convenient structural and property diversification for advanced single-crystal electronics.
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21 August 2021
Rapid Communication|
August 17 2021
Modulation of π-stacking modes and photophysical properties of an organic semiconductor through isosteric cocrystallization
Special Collection:
2021 JCP Emerging Investigators Special Collection
Gonzalo Campillo-Alvarado
;
Gonzalo Campillo-Alvarado
a)
1
Department of Chemical and Biomolecular Engineering, University of Illinois Urbana-Champaign
, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA
a)Author to whom correspondence should be addressed: [email protected]
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Michael Bernhardt;
Michael Bernhardt
1
Department of Chemical and Biomolecular Engineering, University of Illinois Urbana-Champaign
, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA
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Daniel W. Davies
;
Daniel W. Davies
1
Department of Chemical and Biomolecular Engineering, University of Illinois Urbana-Champaign
, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA
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Julio A. N. T. Soares;
Julio A. N. T. Soares
2
Frederick Seitz Materials Research Laboratories Central Facilities, University of Illinois Urbana-Champaign
, 104 South Goodwin Avenue, Urbana, Illinois 61801, USA
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Toby J. Woods
;
Toby J. Woods
3
School of Chemical Sciences, University of Illinois Urbana-Champaign
, 505 S. Mathews Avenue, Urbana, Illinois 61801, USA
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Ying Diao
Ying Diao
1
Department of Chemical and Biomolecular Engineering, University of Illinois Urbana-Champaign
, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA
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a)Author to whom correspondence should be addressed: [email protected]
Note: This paper is part of the 2021 JCP Emerging Investigators Special Collection.
J. Chem. Phys. 155, 071102 (2021)
Article history
Received:
June 11 2021
Accepted:
August 03 2021
Citation
Gonzalo Campillo-Alvarado, Michael Bernhardt, Daniel W. Davies, Julio A. N. T. Soares, Toby J. Woods, Ying Diao; Modulation of π-stacking modes and photophysical properties of an organic semiconductor through isosteric cocrystallization. J. Chem. Phys. 21 August 2021; 155 (7): 071102. https://doi.org/10.1063/5.0059770
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