期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 17, 页码 5289-5296出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203936
关键词
cross-coupling; cyclic voltammetry; fluorine; HOF CH3CN; oligothiophenes; oxygen transfer; UV; Vis spectroscopy
The quest for obtaining conjugated oligothiophene-containing molecules with narrower HOMOLUMO gaps and higher oxidation and reduction potentials is the subject of this study. Molecules containing the bithiophene tetraoxide (2) and the terthiophene hexaoxide (3) moieties were prepared and studied. They were obtained by transferring oxygen atoms to the corresponding dibromo oligothiophenes with the HOFCH3CN complex and then cross-coupling them with either thiophene- or acetylene tin derivatives. The photophysical and electrochemical studies of the products revealed that this particular class of mixed thiophenes is characterized by significantly smaller frontier orbital gaps and higher oxidation and reduction potentials compared with any other arrangement of oligothiophenes including various [all]-S,S-oxygenated thiophene derivatives.
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