Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes
Shixin Fa, Tan-hao Shi, Suzu Akama, Keisuke Adachi, Keisuke Wada, Seigo Tanaka, Naoki Oyama, Kenichi Kato, Shunsuke Ohtani, Yuuya Nagata, Shigehisa Akine & Tomoki Ogoshi
Real time monitoring of chirality transfer processes is necessary to better understand their kinetic properties. Herein, we monitor an ideal chirality transfer process from a statistically random distribution to a diastereomerically pure assembly in real time. The chirality transfer is based on discrete trimeric tubular assemblies of planar chiral pillararenes, achieving the construction of diastereomerically pure trimers of pillararenes through synergistic effect of ion pairing between a racemic rim-differentiated pillararene pentaacid bearing five benzoic acids on one rim and five alkyl chains on the other, and an optically resolved pillararene decaamine bearing ten amines. When the decaamine is mixed with the pentaacid, the decaamine is sandwiched by two pentaacids through ten ion pairs, initially producing a statistically random mixture of a homochiral trimer and two heterochiral trimers. The heterochiral trimers gradually dissociate and reassemble into the homochiral trimers after unit flipping of the pentaacid, leading to chirality transfer from the decaamine and producing diastereomerically pure trimers.
chirality, homochiral, nanotubes