<p>Annulation reaction of a 1,1′-(1,3-butadiyne)-8,8′-(2,5-thiophene)-bridged carbazole dimer <bold>10</bold> provided the carbazole-based isophlorines <bold>11a–11c</bold> and <bold>12</bold>. The oxidation of <bold>12</bold> generated the corresponding 21-selena-23-thiaporphyrin <bold>13</bold>.</p>