Premium
Diastereospecific Photochemical Dimerization of a Stilbene‐Containing Daisy Chain Monomer in Solution as well as in the Solid State
Author(s) -
Amirsakis Dafni G.,
Elizarov Arkadij M.,
GarciaGaribay Miguel A.,
Glink Peter T.,
Stoddart J. Fraser,
White Andrew J. P.,
Williams David J.
Publication year - 2003
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.200390296
Subject(s) - cyclobutane , chemistry , monomer , photochemistry , solid state , photopolymer , crown ether , regioselectivity , yield (engineering) , diastereomer , polymer chemistry , ether , quantum yield , stereochemistry , crystallography , ion , ring (chemistry) , materials science , organic chemistry , polymer , metallurgy , catalysis , physics , quantum mechanics , fluorescence
A crown ether/dialkylammonium ion hybrid containing a stilbene group self‐assembles into a [c2]daisy chain‐like pseudorotaxane, the solid‐state superstructure of which was confirmed by X‐ray crystallography. Upon irradiation, the pseudorotaxane undergoes an efficient photochemical [2+2] dimerization, both in solution as well as in the solid state, to yield one cyclobutane diastereoisomer with syn‐anti‐syn stereochemistry and head‐to‐tail regiochemistry (see scheme).