Star-shaped dendritic molecules based on carboxylated carbazole and pyrrole as peripheral oxidizable units

The synthesis and spectroscopic characterization of three tricarboxylated pyrrole (Pyr)- and carbazole (Cbz)-containing star-shaped dendritic molecules 1–3 have been described here. Clauson–Kaas, amide coupling and debenzylation reactions have been used as key chemical tools. Electropolymerization of these oxidizable molecules has been investigated. The carboxylated Cbz-based molecules upon oxidative electropolymerization produced stable electroactive polyCOOH polyCbz films.

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► Polycarboxylated carbazole- and pyrrole-based dendritic monomers.
► Carboxylated peripheral building blocks were synthesized in one step.
► Pyrrole-/carbazole-based dendritic monomers were synthesized in three steps.
► Electropolymerization of polycarboxylated monomers was investigated.
► The carbazole-based monomers produced stable functionalized conducting polymer film.