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Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores
Authors: Solanke Parmeshwar | Achelle Sylvain | Cabon Nolwenn | Pytela Oldřich | Barsella Alberto | Caro Bertrand | Robin-le Guen Francoise | Podlesný Jan | Klikar Milan | Bureš Filip
Year: 2016
Type of publication: článek v odborném periodiku
Name of source: Dyes and Pigments
Publisher name: Elsevier Science
Place: Oxford
Page from-to: 129-138
Titles:
Language Name Abstract Keywords
cze Chalkogenové analogy proaromatických pyranylidenů a cyklopenta[c]thiofen-4,6-dion jako elektrondonory a elektronakceptor v efektivních charge-transfer chromoforech. Bylo připraveno patnáct nových push-pull chromoforů na bázi proaromatických pyranylidenových donorů a jejich chalkogenových analogů s rozmanitými elektronakceptorními jednotkami. Modelové molekuly byly navrženy a připraveny s cílem studovat proaromaticitu jako nástroj k ovlivňování základních vlastností push-pull systémů. Všechny cílové chromfory se systematicky obměňovanou strukturou byly podrobeny měření elektrochemických vlastností, absorpčních spekter a EFISH experimentů, současně byly prováděny DFT kalkulace. Chalkogenopyranyliden; push-pull; nelineární optika; přenos náboje; polymethiny
eng Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores 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 pi-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. Chalcogenopyranylidene; Push-pull; Non linear optics; Charge transfer; Polymethines

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