An electron-transfer induced conformational transformation: from non-cofacial “sofa” to cofacial “boat” in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes

Abstract

Electro-active polychromophoric assemblies that undergo clam-like electromechanic actuation represent an important class of organic functional materials. Here, we show that the readily available cyclotetraveratrylene (CTTV) undergoes oxidation-induced folding, consistent with interconversion from a non-cofacial “sofa” conformation to a cofacial “boat” conformer. It is found that the non-cofacial “sofa” conformer of CTTV forms stable electron donor–acceptor complexes with chloranil and DDQ. Electron-transfer induced conformational transformation in CTTV provides a framework for the rational design of novel organic functional molecules.