Bicyclo octene oligothiophenes

Synthesis and properties of cationic -conjugated systems stabilized by bicyclo[2.2.2]octene units including annulated silatropilium ion, thiophene, 1,2-dithiine, 1,4-dithiine, and oligothiophenes 05SL187. 

Other a,co-disubstituted oligothiophenes such as 31 [24], 32 [103], 33 [104], 34 [105], 35 [106] and 36 [98] were characterized by cyclic voltammetry (Scheme 9.23). In 35, bulky bicyclo[2.2.2]octene substituents were introduced to prevent dimerization. Indeed, all oligomers derived from 35 (n = 0, 1, 2, 4) show stable radical cations and dications. In the case of the hexamer derived from 35 with n = 4, the two first one-electron reversible oxidation waves are nearly coalesced ( ox 0. 19, = 0.28 V vs FC/FC+)... 

---