Kinetically and Thermodynamically Controlled Nanostructures of Perylene-Substituted Lophine Derivatives

Supramolecular assemblies have been extensively studied because of their fundamental insights into intermolecular interactions and their potential applications to optoelectronic devices. Among various molecular building units, 2,4,5-triphenylimidazole (lophine) has been extensively studied because the molecule itself gives chemiluminescence and bright fluorescence and because it forms various anisotropic nanostructures. While various potential applications such as to optoelectronic and lasing devices have been reported in lophine-based nanostructures, the relationship among molecular structures, nanostructures, and their optical properties remains elusive. This study reveals that the hydrogen bonding of the imidazole ring plays a crucial role for one-dimensional anisotropic nanostructures and their optical properties. The hydrogen bonding leads to thermodynamically stable nanofibers and gives a monomeric sharp emission, while it also induces ultrafast nonradiative relaxation. On the other hand, the π–π in...