Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4, 6-dione as electron donors and acceptor in efficient charge-transfer chromophores. (November 2016)

• Record Type: Journal Article
• Authors: Solanke, Parmeshwar; Achelle, Sylvain; Cabon, Nolwenn; Pytela, Oldřich; Barsella, Alberto; Caro, Bertrand; Robin-le Guen, Françoise; Podlesný, Jan; Klikar, Milan; Bureš, Filip
• Is Part Of: Dyes and pigments. Volume 134(2016)
• Page Start: 129
• Page End: 138
• Publication Date: 2016-11
• Subjects: Chalcogenopyranylidene -- Push-pull -- Non linear optics -- Charge transfer -- Polymethines; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.07.008
• Languages: English
• ISSNs: 0143-7208

Abstract

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. Graphical abstract: Highlights: Fifteen push-pull chromophores based on (chalcogeno)pyranilidene donor were designed. Electrochemistry, absorption spectra, and EFISH experiment were performed. Cyclopenta[ c ]thiophen-4, 6-dione has also been developed as electron withdrawing part.