A1 Journal article (refereed)
Unravelling substitution effects on charge transfer characteristics in cocrystals of pyrene based donors and 3,5-dinitrobenzoic acid (2019)

Mandal, A., Rissanen, K., & Mal, P. (2019). Unravelling substitution effects on charge transfer characteristics in cocrystals of pyrene based donors and 3,5-dinitrobenzoic acid. CrystEngComm, 21(29), 4401-4408. https://doi.org/10.1039/c9ce00561g

JYU authors or editors

Publication details

All authors or editors: Mandal, Arkaleka; Rissanen, Kari; Mal, Prasenjit

Journal or series: CrystEngComm

eISSN: 1466-8033

Publication year: 2019

Volume: 21

Issue number: 29

Pages range: 4401-4408

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/c9ce00561g

Publication open access: Not open

Publication channel open access: 

Abstract

Here we report charge-transfer cocrystals composed of pyrene and amino/bromopyrene as π-donors (D) and 3,5-dinitrobenzoic acid (A) as a π-acceptor. The 1:1 cocrystals of pyrene/1-aminopyrene adopt a ⋯DADADA⋯ mixed stack arrangement whereas the 2:1 cocrystal of 1-bromopyrene and 3,5-dinitrobenzoic acid shows ⋯DDADDA⋯ stacking. Crystallographic, spectral and theoretical studies reveal that the frontier molecular orbital energy level rather than the π-donor strength plays the governing role in predicting charge transfer. In addition, a theoretical study demonstrates that the ambipolar semiconductor nature in cocrystals of the pyrene/aminopyrene donor and the p-type nature of bromopyrene with the 3,5-dinitrobenzoic acid acceptor are governed solely by the supramolecular structure and not by other factors.

Keywords: supramolecular chemistry; organic compounds; crystals; chemical bonds

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1