We report here a new strategy towards functionalization of oligothiophenes that consists of the chemical transformation of thienyl sulfurs into the corresponding S,S-dioxides. We show that this kind of functionalization, which implies the dearomatization of the thiophene rings, leads to very stable oligomers with increased electron delocalization and has also a dramatic effect on their electron affinity as deduced from their electrochemical reduction potential. It is worth mentioning that the synthesis and the characterization of unsubstituted thiophene S,S-dioxide has been reported only very recently and that only S,S-dioxides derived from polysubstituted thiophene are stable at room temperature. So far, no electrochemical data on this kind of compound have yet been published.
Barbarella G., Favaretto L., Zambianchi M., Pudova O., Arbizzani C., Bongini A., et al. (1998). From easily oxidized to easily reduced thiophene-based materials. ADVANCED MATERIALS, 10(7), 551-554 [10.1002/(SICI)1521-4095(199805)10:7<551::AID-ADMA551>3.0.CO;2-Y].
From easily oxidized to easily reduced thiophene-based materials
Favaretto L.;Zambianchi M.;Arbizzani C.Investigation
;Bongini A.;Mastragostino M.
1998
Abstract
We report here a new strategy towards functionalization of oligothiophenes that consists of the chemical transformation of thienyl sulfurs into the corresponding S,S-dioxides. We show that this kind of functionalization, which implies the dearomatization of the thiophene rings, leads to very stable oligomers with increased electron delocalization and has also a dramatic effect on their electron affinity as deduced from their electrochemical reduction potential. It is worth mentioning that the synthesis and the characterization of unsubstituted thiophene S,S-dioxide has been reported only very recently and that only S,S-dioxides derived from polysubstituted thiophene are stable at room temperature. So far, no electrochemical data on this kind of compound have yet been published.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
