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Paper | Regular issue | Vol 91, No. 2, 2015, pp.313-331
Published online, 20th January, 2015
DOI: 10.3987/COM-14-13145
Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives

Maurizio D'Auria,* Ambra Guarnaccio, Rocco Racioppi, Antonio Santagata, and Roberto Teghil

*Departament of Science, Università della Basilicata, viale dell'Ateneo Lucano 10, 00137, Italy


The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 nm and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo-[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 nm.