Synthesis and Evaluation of Molecular Rotors with Large and Bulky tert-Butyldiphenylsilyloxy-Substituted Trityl Stators

摘要

The search for voluminous stators that may accommodate large rotator units and speed rotational dynamics in the solid state led us to investigate a simple and efficient method for the synthesis of molecular rotors with tert-butyldiphenylsilyl-protected (TBDPS) triphenylmethyl stators. Additionally, solid state characterization of these systems with two-, four-, and six-TBDPS groups provided us with a description of their crystallinity and thermal stability. Among them, molecular rotor 7c with the largest and most symmetric stator resulting from six peripheral silyl groups showed the best tendency to crystallize, and the study of its isotopologue 7c-d4 by solid state 2H NMR revealed a 2-fold motion of the 1,4-diethynylphenylene-d4 rotator in the kHz regime.