Document Detail

Regioselective photodimerization of cinnamic acids in water: Templation with cucurbiturils.
MedLine Citation:
PMID:  16922539     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Cinnamic acids upon irradiation in solution undergo geometric isomerization while dimerizing to different dimers in the crystalline state. Controlling the nature of the dimer formed upon irradiation remains a challenging task. We have aligned a variety of cinnamic acid molecules in a head-head fashion employing cucurbit[8]uril, a weakly water soluble host as a template. The water solubility of cucurbit[8]uril is enhanced by inclusion of water soluble cinnamic acids and positions the olefins in an arrangement that favors the formation of syn head-head cyclobutanes in near quantitative yields. This methodology works in both solid state as well as in aqueous solution. Irradiation of cinnamic acid complexes with gamma-cyclodextrin has been carried out as a comparison. We find that while cucurbit[8]uril functions well both in solid state and aqueous solution, cyclodextrin works best as solid complexes only. Consistent with the postulated requirement of large cavities for templating olefins to dimerization, irradiation of complexes of cinnamic acid with cucurbit[7]uril resulted in only the corresponding cis isomers.
Mahesh Pattabiraman; Lakshmi S Kaanumalle; Arunkumar Natarajan; V Ramamurthy
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Langmuir : the ACS journal of surfaces and colloids     Volume:  22     ISSN:  0743-7463     ISO Abbreviation:  Langmuir     Publication Date:  2006 Aug 
Date Detail:
Created Date:  2006-08-22     Completed Date:  2007-09-21     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9882736     Medline TA:  Langmuir     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7605-9     Citation Subset:  -    
Department of Chemistry, University of Miami, Coral Gables, Florida 33124, USA.
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