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Solid state supramolecular structure of diketopyrrolopyrrole chromophores: correlating stacking geometry with visible light absorption

Pop, Flavia; Lewis, William; Amabilino, David B.

Authors

Flavia Pop

William Lewis

David B. Amabilino



Abstract

Mono- and di-alkylated 1,4-diketo-3,6-dithiophenylpyrrolo[3-4-c]pyrrole derivatives (TDPPs) have been synthesised and their solid state packing and absorption properties have been correlated. In this library of compounds the bulkier substituents distort the geometry of the chromophores and shift the lowest energy absorption band as a consequence of reduced π–π stacking and inter-chromophore overlap. Longitudinal displacement of the conjugated core is affected by donor–acceptor intermolecular interactions and twisting of the thiophene ring out of the plane of the DPP core, whereas lateral displacement was correlated to distortion of the NLactam–C(R) bond out of the plane of the DPP core. The di-substituted TDPP with hexyl units exhibit high molecular planarity, strong close packing of the conjugated core and significant red shift of the maximum of absorption in the solid, whereas the mono-substituted compounds with hexyl and ethyl acetate units are the least distorted of the series because of strong intermolecular hydrogen bonding that increases the molecular overlap and planarity of the chromophores. Therefore the family of mono-substituted TDPPs and more specifically the ones with ethyl acetate substituents show good potential for modulating the molecular geometry and optimizing the charge transport in materials for organic electronic applications.

Citation

Pop, F., Lewis, W., & Amabilino, D. B. (in press). Solid state supramolecular structure of diketopyrrolopyrrole chromophores: correlating stacking geometry with visible light absorption. CrystEngComm, 18(46), https://doi.org/10.1039/C6CE02157C

Journal Article Type Article
Acceptance Date Nov 3, 2016
Online Publication Date Nov 3, 2016
Deposit Date Mar 27, 2017
Publicly Available Date Mar 27, 2017
Journal CrystEngComm
Electronic ISSN 1466-8033
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 18
Issue 46
DOI https://doi.org/10.1039/C6CE02157C
Public URL https://nottingham-repository.worktribe.com/output/830200
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2016/CE/C6CE02157C#!divAbstract

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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