(Principal Investigator's) The study of novel electrical and optical sensors for the enantioselective recognition of chiral organic compounds and drug molecules has been proposed. These sensors are constructed by using optically active binaphthyl-based main chain chiral conjugated materials. Different molecular receptors such as crown ethers, polyammonium macrocycles and diboronic acid functions will be incorporated into the chiral conjugated polymers. These materials will be used to analyze molecules such as chiral amines, amino acids, chiral phosphates, chiral carboxylates, chiral alcohols and sugars. Due to the chirality of these novel conjugated polymers, they will be able to differentiate the enantiomers of the substrates. The synthesis and study of binaphthyl-based chiral conjugated dendrimers is also proposed. In addition to the research on the polymers with stable main chain chiral configuration, we also propose to prepare an achiral cross-conjugated polymer that can exhibit main chain chirality in the presence of chiral guests. This induced main chain chirality will be used to discriminate the enantiomers of chiral molecules. Through the study of these conjugated chiral host polymers, it is expected to develop a class of highly sensitive and enantioselective sensors with rapid responses. The interaction of these sensors with substrates will be investigated by analyzing their UV-vis absorptions, fluorescences, phosphorescences, CD effects and electrochemistry. This study will lead to fundamentally new sciences and important practical applications.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM058454-02
Application #
6138669
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
1999-01-01
Project End
2001-06-30
Budget Start
2000-01-01
Budget End
2001-06-30
Support Year
2
Fiscal Year
2000
Total Cost
$103,600
Indirect Cost
Name
University of Virginia
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
001910777
City
Charlottesville
State
VA
Country
United States
Zip Code
22904
Wang, Qin; Chen, Xi; Tao, Lan et al. (2007) Enantioselective fluorescent recognition of amino alcohols by a chiral tetrahydroxyl 1,1'-binaphthyl compound. J Org Chem 72:97-101
Wang, Qin; Chen, Shan-Yong; Yu, Xiao-Qi et al. (2007) 1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes. Tetrahedron 63:4422-4428
Li, Zi-Bo; Liu, Tian-Dong; Pu, Lin (2007) Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes. J Org Chem 72:4340-3
Li, Zi-Bo; Lin, Jing; Sabat, Michal et al. (2007) Enantioselective fluorescent recognition of chiral acids by cyclohexane-1,2-diamine-based bisbinaphthyl molecules. J Org Chem 72:4905-16
Rajaram, Amaresh R; Pu, Lin (2006) Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids. Org Lett 8:2019-21
Hyacinth, Marilise; Chruszcz, Maksymilian; Lee, Ki Sung et al. (2006) Supramolecular assemblies of chiral propargylic alcohols. Angew Chem Int Ed Engl 45:5358-60
Qin, Ying-Chuan; Liu, Lan; Pu, Lin (2005) On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes. Org Lett 7:2381-3
Li, Zi-Bo; Lin, Jing; Qin, Ying-Chuan et al. (2005) Enantioselective fluorescent recognition of a soluble ""supported"" chiral acid: toward a new method for chiral catalyst screening. Org Lett 7:3441-4
Pu, Lin (2004) Fluorescence of organic molecules in chiral recognition. Chem Rev 104:1687-716
Li, Zi-Bo; Lin, Jing; Zhang, Hui-Chang et al. (2004) Macrocyclic bisbinaphthyl fluorophores and their acyclic analogues: signal amplification and chiral recognition. J Org Chem 69:6284-93

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