Boat-to-boat conformation inversions of cyclobis[7,8-(para-quinodimethane)-3,7-(9-(p-tolyl)-9H-carbazole)] in the neutral and tetracationic state

Abstract

We report the synthesis of macrocyclic cyclobis[7,8-(para-quinodimethane)-3,7-(9-(p-tolyl)-9H-carbazole)] CBQCz. We found that CBQCz showed temperature-dependent and four-electron oxidative conformation changes. Both CBQCz and CBQCz⁴⁺ possess boat-to-boat conformation inversions. The smaller inverted energy and less curved structure of CBQCz⁴⁺ are due to the conjugated effect of tetracations.