Design of rotational potential in a phenyltriptycene molecular rotor by exploiting CH/π-interaction between tripticil hydrogen and phenyl.

ABSTRACT

The chemistry of artificial molecular rotors has recently attracted considerable attention in the field of molecular machines. Phenyltriptycene could be used as a stepwise molecular rotor because it is composed of a phenyl rotor and a triptycene stator, in which the rotational potential can be designed by introducing substituents. In this study, a novel design of the relative energies among three rotamers of a substituted phenyltriptycene by exploiting the CH/π-interaction between a peri-hydrogen and phenyl was investigated. First, the structures of two different phenyltriptycenes were compared to confirm CH/π-interactions. Second, the effects of the substituents of 1,4,5-trichloro-3',5'-dimethoxyphenyltriptycene on the relative energies were investigated by structural analysis, temperature-dependent nuclear magnetic resonance studies, and density functional theory calculations. The obtained results should facilitate the design of novel molecular switches and/or molecular rotors.