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Poly(benzotriazole)s, P(BTz)s, having an n-type benzotriazole-π-conjugated main chain and p-type and electrochemically polymerizable carbazole (CBz) pendant groups, −(CH 2 ) m −CBz ( m = 12 or 6) groups, were synthesized by Ni− (for homopolymers) and Pd-promoted (for a copolymer) organometallic polycondensations. The copolymer between benzotriazole with the −(CH 2 ) 12 −CBz pendant and p -phenylene was soluble in organic solvents and showed a number-average molecular weight ( M n ) of 27000 in the GPC analysis. The homopolymers ( m = 12, 6) were less soluble, and about half of the polymer was soluble in CHCl 3 in the case of m = 12; the soluble part gave an M n value of 4700. The polymers were photoluminescent with quantum yields of 50−70%. Cyclic voltammograms of the polymers revealed that the polymers were active in electrochemical n-doping in accord with the electron-accepting nature of the benzotriazole main chain. Application of electrochemical oxidation potential to the polymer made the polymer insoluble due to occurrence of electrochemical polymerization of the CBz unit.
Tanimoto et al. (2006) studied this question.