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A tetrathiafulvalene-functionalized schiff base macrocycle: synthesis, electrochemical, and photophysical properties
Authors:Ying-Fen RanCarmen Blum  Shi-Xia Liu  Lionel Sanguinet  Eric LevillainSilvio Decurtins
Affiliation:a Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
b Université d’Angers, Institut des Sciences et Technologies Moléculaires d’Angers, MOLTECH Anjou(Ex CIMA), CNRS UMR 6200, 2 Bd Lavoisier, 49045 Angers Cedex, France
Abstract:
Highly selective formation of 2+2 macrocycle 1 from 2,5-bis(3-formyl-2-hydroxyphenyl)-1,3,4-oxadiazole and a diamine-functionalized tetrathiafulvalene derivative is reported. Its electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis-NIR spectroscopy. Particularly, its largely extended π-conjugation renders this novel macrocycle simultaneously a good multielectron donor and a strong chromophore, which is rationalized on the basis of density functional theory.
Keywords:Charge transfer   Donor-acceptor systems   Electrochemistry   Schiff base   Tetrathiafulvalene
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