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Crystallographic and Chiroptical Studies on Tetraarylferrocenes for Use as Chiral Rotary Modules for Molecular Machines
Author(s) -
Muraoka Takahiro,
Kinbara Kazushi,
Wakamiya Atsushi,
Yamaguchi Shigehiro,
Aida Takuzo
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601098
Subject(s) - absolute configuration , azobenzene , circular dichroism , chemistry , crystallography , ferrocene , crystal structure , derivative (finance) , enantiomer , crystal (programming language) , molecular machine , stereochemistry , molecule , materials science , nanotechnology , organic chemistry , computer science , electrode , financial economics , programming language , economics , electrochemistry
A crystal structure of the racemic form of chiral molecular scissors 1 with a trans configuration at the azobenzene unit ( rac ‐ trans ‐ 1 ), in which the scissors adopt a closed geometry with two blade phenyl groups that overlap each other, was successfully determined. X‐ray crystallographic determination of the structure of (1 S ,1′ S )‐ 10 , which is a derivative of the key precursor of trans ‐ 1 , was also successful. On the basis of the crystal structure of (1 S ,1′ S )‐ 10 , the absolute configuration of 1 and related molecular machines, such as molecular pedal 2 , and self‐locking rotor 3 , which all contain a chiral tetrasubstituted ferrocene module, were determined. A correlation between the absolute configuration and the circular dichroism properties of these molecular machines and their synthetic precursors was also determined.