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Updated: Aug 30, 2025

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Published on: July 27, 2022
Design of rotational potential in a phenyltriptycene molecular rotor by exploiting CH/π-interaction between tripticil
Hazuki Inami1, Yusuke Inagaki1, Wataru Setaka1
1Division of Applied Chemistry, Faculty of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan. wsetaka@tmu.ac.jp.
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.
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