Tetraptycene derivatives: synthesis, structure and their self-assemblies in solid state

Abstract

As iptycenes of arenes are fused to a bicyclo[2.2.2]octatriene bridgehead system, there are only odd-sequenced iptycene family members, such as triptycene, pentiptycene and heptiptycene. In order to ensure the completeness of the iptycene family sequence, developing even-sequenced iptycene family members is of great significance. The dimer of anthracene derivatives is a class of tricyclo[2.2.2.2]dodetetraene molecules with four separate phenyl rings, which are structurally similar to the iptycene family and herein referred to as “tetraptycene”. In this work, a series of hydroxyl or methoxy-substituted tetraptycene derivatives from the photochemical reactions of anthracene derivatives was reported. These tetraptycene derivatives were characterized using nuclear magnetic resonance (NMR), mass spectrum (MS) and single-crystal X-ray diffraction (SC-XRD). Moreover, their self-assemblies in the solid state were further discussed. Their properties of modifiability, asymmetry, and rigidity indicate their superiority as novel monomers to construct functional material architectures.