Optical Effect of Varying Acceptors in Pyrene Donor–Acceptor–Donor Chromophores

Three donor–acceptor–donor (D–A–D) pyrene chromophores are described and compared by DFT computations. The two properties of low energy photon absorption and low energy electrochemical reduction are demonstrated through a pyrene framework. Altering the electron‐acceptor strength of the pyrene core b...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-07, Vol.2017 (27), p.3980-3985
Main Authors: Keller, Samantha N., Bromby, Ashley D., Sutherland, Todd C.
Format: Article
Language:English
Subjects:
Absorption spectra
Arenes
Chromophores
Energy levels
Functional organic materials
Ketones
Molecular electrochemistry
Organic semiconductors
Oxidation
Photon absorption
Sulfur heterocycles
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Summary:Three donor–acceptor–donor (D–A–D) pyrene chromophores are described and compared by DFT computations. The two properties of low energy photon absorption and low energy electrochemical reduction are demonstrated through a pyrene framework. Altering the electron‐acceptor strength of the pyrene core by chemical oxidation or installation of a thiadiazole dioxide heterocycle results in the formation of D–A–D chromophores with absorption bands up to 900 nm and LUMO energy levels of approximately –4.1 eV vs. vacuum. A route to pyrene‐based donor–acceptor–donor (D–A–D) chromophores with high electron affinity was developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700630