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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
22
pubmed:dateCreated
2002-10-25
pubmed:abstractText
A series of well-defined enantiopure 1,1'-binaphthyl-based oligomers linked through their 6,6'-positions, ranging from quaternaphthol to decanaphthol, have been synthesized by Suzuki and Stille coupling reactions. These novel oligonaphthyls have been characterized by (1)H and (13)C[(1)H] NMR spectroscopy and high-resolution mass spectrometry. A combination of X-ray structural and CD studies suggests that these oligonaphthyls adopt zigzag but not helical conformations. As the chain length increases, the compounds show enhanced fluorescence. The fluorescence intensity of oligonaphthols is almost 2 orders of magnitude higher than that of 1,1'-bi-2-naphthol and can be effectively and enantioselectively quenched with trans-1,2-diaminocyclohexane with an enantioselectivity factor of 1.24. The present work thus demonstrates the potential of constructing chiral sensory materials based on well-defined enantiopure oligonaphthols.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Nov
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
1
pubmed:volume
67
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
7577-86
pubmed:year
2002
pubmed:articleTitle
Well-defined enantiopure 1,1'-binaphthyl-based oligomers: synthesis, structure, photophysical properties, and chiral sensing.
pubmed:affiliation
Department of Chemistry, CB#3290, University of North Carolina, Chapel Hill 27599, USA.
pubmed:publicationType
Journal Article