Abstract
The reaction of 3,3′-diaminobenzidine (DAB) with 1,4-benzenedimethanol (BDM) in the presence of a RuCl2(PPh3)3 catalyst yielded oligobenzimidazoles (OBIs) with OH groups at both ends. The degrees of oligomerization (DO) of the OBIs depended on the monomer feed ratio and reaction temperature. The reaction of the OBIs with CH3(CH2)mI (m = 0, 3, 5, 7, and 9) assisted by KOH caused both N- and O-alkylation, yielding alkylated OBI-(CH2)mCH3. The UV–vis measurements suggest that OBI-CH3 forms a 1:2 charge transfer complex with 7,7,8,8-tetracyanoquinodimethane (TCNQ). The intensity of OBI-CH3 photoluminescence decreased depending on the amount of TCNQ added to the solution. The quenching behavior was investigated by Stern–Volmer analysis. The OBIs and OBI-Rs were electrochemically oxidized and reduced. The powder X-ray diffraction patterns suggest that the OBI-Rs self-assemble into ordered structures in the solid state.
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