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A Supramolecular Protecting Group Strategy Introduced to the Organic Solid State: Enhanced Reactivity through Molecular Pedal Motion
Author(s) -
Elacqua Elizabeth,
Kaushik Poonam,
Groeneman Ryan H.,
Sumrak Joseph C.,
Bučar DejanKrešimir,
MacGillivray Leonard R.
Publication year - 2012
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.201106842
Subject(s) - reactivity (psychology) , supramolecular chemistry , olefin fiber , solid state , acceptor , chemistry , computer science , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , catalysis , physics , medicine , alternative medicine , pathology , condensed matter physics
A supramolecular protecting group strategy has been applied to achieve solid‐state photodimerizations of olefins lined with a combination of hydrogen‐bond‐donor and ‐acceptor groups. Esters were used as protecting groups to generate head‐to‐head photodimers that were readily converted into diacids. A protected olefin equipped with a stilbene unit exhibits enhanced reactivity that is ascribed to pedal motions in the solid state (orange hexagons: template: blur circles: recognition sites).