A synthesis of 7-chloropyrido[1,2-a]benzimidazole-8,9-dione derivatives bearing fragments of widely used acceptor units has been performed, and their structures were investigated using the principle of coupled polymethines. Their electronic and electrochemical properties have also been studied. Compounds were isolated in both salt and neutral forms and depending on the introduced substituent can exist as o-quinone or p-quinone methide.