Octadehydrodibenzo[12]annulene-Based Organogels: Two Methyl Ester Groups Prevent Crystallization and Promote Gelation

摘要

Recently, π-conjugated cyclic systems involving benzene rings and acetylene units, the dehydrobenzoannulenes (DBAs), have attracted substantial interest from the viewpoint of acting as building blocks of supramolecular assemblies, along with their optoelectronic functionality, rigid, well-defined molecular structures, and extensively delocalized π electrons. To date, a handful of superstructures based on triangular DBAs have been reported. They include one-dimensional (1D) fibrous superstructures in films from Die-derich, Nielsen et al. and Iyoda et al. , micelles and liquid crystals from Tew et al., and two-dimensionally ordered networks at the liquid-solid interface from Tobe, De Feyter et al. More recently, we also demonstrated that a single crystal composed of one-dimensionally π-stacked DBA exhibited highly anisotropic charge-carrier mobility. However, superstructures of DBAs have not been extensively reported except for the case of crystals, and there has been no report on organogels based on DBAs. One of the reasons for the lack of DBA superstructures is that the affinity interactions between DBA rings are weaker than those of other systems, such as discotic graphene-like molecules, owing to weaker π-π interactions of DBA rings containing sp-hybridized carbon atoms. Indeed, for gelators, strong and highly directional intermolecular interactions are required.