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Optical Effect of Varying Acceptors in Pyrene Donor–Acceptor–Donor Chromophores
Author(s) -
Keller Samantha N.,
Bromby Ashley D.,
Sutherland Todd C.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700630
Subject(s) - chromophore , pyrene , chemistry , photochemistry , acceptor , absorption (acoustics) , homo/lumo , electrochemistry , electron acceptor , electron donor , molecule , organic chemistry , catalysis , optics , physics , electrode , condensed matter physics
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.