| Enantioselective fluorescent recognition of chiral acids by cyclohexane-1,2-diamine-based bisbinaphthyl molecules. | |
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MedLine Citation:
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PMID: 17530897 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The cyclohexane-1,2-diamine-based bisbinaphthyl macrocycles (S)-/(R)-5 and their cyclic and acyclic analogues are synthesized. The interactions of these compounds with various chiral acids are studied. Compounds (S)-/(R)-5 exhibit highly enantioselective fluorescent responses and high fluorescent sensitivity toward alpha-hydroxycarboxylic acids and N-protected amino acids. Among these interactions, (S)-mandelic acid (10(-3) M) led to over 20-fold fluorescence enhancement of (S)-5 (1.0 x 10(-5) M in benzene/0.05% DME) at the monomer emission, and (S)-hexahydromandelic acid (10(-3) M) led to over 80-fold fluorescence enhancement. These results demonstrate that (S)-5 is useful as an enantioselective fluorescent sensor for the recognition of the chiral acids. On the basis of the study of the structures of (S)-5 and the previously reported 1,2-diphenylethylenediamine-based bisbinaphthyl macrocycle (S)-4, the large fluorescence enhancement of (S)-5 with a chirality-matched alpha-hydroxycarboxylic acid is attributed to the formation of a structurally rigidified host-guest complex and the further interaction of this complex with the acid to suppress the photoinduced electron-transfer fluorescent quenching caused by the nitrogens in (S)-5. |
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Authors:
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Zi-Bo Li; Jing Lin; Michal Sabat; Marilise Hyacinth; Lin Pu |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2007-05-27 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Jun |
Date Detail:
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Created Date: 2007-06-15 Completed Date: 2007-09-13 Revised Date: 2013-06-06 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4905-16 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acids, Acyclic Circular Dichroism Crystallography, X-Ray Cyclohexylamines / chemical synthesis, chemistry* Macrocyclic Compounds / chemistry Magnetic Resonance Spectroscopy Mandelic Acids / chemistry* Models, Molecular Molecular Structure Naphthalenes / chemistry* Spectrometry, Fluorescence Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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R01 EB002037-05/EB/NIBIB NIH HHS; R01 EB002037-06/EB/NIBIB NIH HHS; R01 GM058454-01/GM/NIGMS NIH HHS; R01 GM058454-02/GM/NIGMS NIH HHS; R01 GM058454-03A1/GM/NIGMS NIH HHS; R01 GM058454-04/GM/NIGMS NIH HHS; R01EB002037-05/EB/NIBIB NIH HHS; R01GM58454/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Acids, Acyclic; 0/Cyclohexylamines; 0/Macrocyclic Compounds; 0/Mandelic Acids; 0/Naphthalenes; 694-83-7/1,2-cyclohexanediamine; NH496X0UJX/mandelic acid |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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