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Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface
Author(s) -
Ishikawa Daisuke,
Mori Taizo,
Yonamine Yusuke,
Nakanishi Waka,
Cheung David L.,
Hill Jonathan P.,
Ariga Katsuhiko
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503363
Subject(s) - monolayer , torsion (gastropod) , molecule , molecular dynamics , materials science , amphiphile , mechanochemistry , crystallography , chemical physics , chemistry , nanotechnology , computational chemistry , organic chemistry , composite material , copolymer , medicine , surgery , polymer
Gradual and reversible tuning of the torsion angle of an amphiphilic chiral binaphthyl, from −90° to −80°, was achieved by application of a mechanical force to its molecular monolayer at the air–water interface. This 2D interface was an ideal location for mechanochemistry for molecular tuning and its experimental and theoretical analysis, since this lowered dimension enables high orientation of molecules and large variation in the area. A small mechanical energy (<1 kcal mol −1 ) was applied to the monolayer, causing a large variation (>50 %) in the area of the monolayer and modification of binaphthyl conformation. Single‐molecule simulations revealed that mechanical energy was converted proportionally to torsional energy. Molecular dynamics simulations of the monolayer indicated that the global average torsion angle of a monolayer was gradually shifted.