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

• Published in: Dyes and pigments Vol. 134; pp. 129 - 138
• Main Authors: Solanke, Parmeshwar, Achelle, Sylvain, Cabon, Nolwenn, Pytela, Oldřich, Barsella, Alberto, Caro, Bertrand, Robin-le Guen, Françoise, Podlesný, Jan, Klikar, Milan, Bureš, Filip
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.11.2016; Elsevier
• Subjects: Absorption spectra; Chalcogenopyranylidene; Charge transfer; Chemical Sciences; Chromophores; Dyes; Electrochemistry; Mathematical models; Non linear optics; Pigments; Polymethines; Push-pull; Synthesis; Thiophenes; Polymethines; Charge transfer; Chalcogenopyranylidene; Push-pull; Non linear optics; Structural variations; Push pull; Fundamental properties; Push-pull chromophores; Chromophores; Electronwithdrawing; Electron acceptor moieties
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2016.07.008

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. [Display omitted] •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.