Document Detail


Enantioselective fluorescent recognition of chiral acids by cyclohexane-1,2-diamine-based bisbinaphthyl molecules.
MedLine Citation:
PMID:  17530897     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Zi-Bo Li; Jing Lin; Michal Sabat; Marilise Hyacinth; Lin Pu
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2007-05-27
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Jun 
Date Detail:
Created Date:  2007-06-15     Completed Date:  2007-09-13     Revised Date:  2013-06-06    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4905-16     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
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MeSH Terms
Descriptor/Qualifier:
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:
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:
0/Acids, Acyclic; 0/Cyclohexylamines; 0/Macrocyclic Compounds; 0/Mandelic Acids; 0/Naphthalenes; 694-83-7/1,2-cyclohexanediamine; NH496X0UJX/mandelic acid
Comments/Corrections

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