Premium
Endo and exo phenylene‐bridged hetero (O,S) silacrown ether rotors including an unexpected structural example of the chloromethyl exchange rule for 1,4‐bis(X 2 methylsilyl)‐ benzene, XCl, Me
Author(s) -
MettaMagana Alejandro J.,
VargasPineda Diana G.,
MartinezPerez Carlos A.,
LopezCardoso Marcela,
Pannell Keith H.
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1721
Subject(s) - chemistry , moiety , phenylene , ether , diastereomer , crystal structure , solvent , molecule , crystal (programming language) , benzene , crystallography , stereochemistry , organic chemistry , polymer , computer science , programming language
Artificial molecular rotors are of current interest because of the various applications that they could have as materials. However, many of them have the common problem of interdigitation and solvent inclusion in the crystal structure. In this work, we prepare a potential rotor with a stator formed by a sila‐hetero(O, S) crown ether moiety and the phenylene bridge as rotator. The use of the sulfur atoms in the stator allows the formation of HB avoiding those common problems. The study of the potential activity as molecular rotors was done via structural analysis by single crystal X‐ray diffraction, comparing them with previously reported rotors for which the activation energies have been reported. A comparison between the exo and endo diastereoisomers was done, showing that the change in stereochemistry affects the conformation, making one of them a better rotor. In addition, we found that the crystal structure of the intermediate 1,4‐bis(dichloro‐methylsilyl)‐benzene represents an example of the non‐applicability of the so‐called chloro‐methyl exchange rule, with four groups substituted. Copyright © 2010 John Wiley & Sons, Ltd.