Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores - Archive ouverte HAL Access content directly
Journal Articles Dyes and Pigments Year : 2016

Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores

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Abstract

Fifteen new push-pull chromophores based on a proaromatic pyranylidene donor and its chalcogen analogues and various electron acceptor moieties were synthesized in a straightforward manner. These model molecules were designed and prepared to investigate the concept of proaromaticity as a tool to tune the fundamental properties of push-pull systems. All target chromophores with systematically varied structure were further investigated by electrochemistry, absorption spectra, and EFISH experiment in conjunction with DFT calculations. Employing structural variations such as chalcogen/acceptor replacement, extension of the π-system, and the position of substitution along the pyran ring, the HOMO-LUMO gap can be tuned within the range of 2.18 to 1.41 eV. A new and powerful electron withdrawing moiety, combining features of polarizable thiophene and successful indane-1,3-dione acceptor, cyclopenta[c]thiophen-4,6-dione (ThDione) has also been developed. © 2016 Elsevier Ltd

Dates and versions

hal-01367232 , version 1 (15-09-2016)

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P. Solanke, S. Achelle, N. Cabon, O. Pytela, A. Barsella, et al.. Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores. Dyes and Pigments, 2016, 134, pp.129--138. ⟨10.1016/j.dyepig.2016.07.008⟩. ⟨hal-01367232⟩
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