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Title: Chiral recognition polymer and its use to separate enantiomers

Abstract

A new polymeric material, a process for forming the material and method of using the material to separate enantiomers of chiral compounds, particularly amino acids and pharmaceuticals are disclosed. A polymeric material can be formed from polyaniline doped with a chiral acid and then extracted with a suitable base. This leaves behind a polymeric material which preferentially traps, and then selectively releases, one enantiomer of a chiral mixture brought in contact with the surface of the polymeric material. In particular, when polyaniline is doped with either R- or S-camphorsulfonic acid (CSA) it takes on a chiral structure. Removing the chiral acid dopant leads to a new chiral polyaniline. The dedoped chiral polyanilines have the ability to discriminate among enantiomers of many compounds which exist in chiral mixtures.

Inventors:
; ;
Issue Date:
Research Org.:
Univ. of California, Oakland, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1531438
Patent Number(s):
6265615
Application Number:
09/322,327
Assignee:
The Regents of the University of California (Oakland, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08G - MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
DOE Contract Number:  
N00014-97-1-0888
Resource Type:
Patent
Resource Relation:
Patent File Date: 1999-05-28
Country of Publication:
United States
Language:
English

Citation Formats

Kaner, Richard B., Knobler, Charles M., and Guo, Hailan. Chiral recognition polymer and its use to separate enantiomers. United States: N. p., 2001. Web.
Kaner, Richard B., Knobler, Charles M., & Guo, Hailan. Chiral recognition polymer and its use to separate enantiomers. United States.
Kaner, Richard B., Knobler, Charles M., and Guo, Hailan. Tue . "Chiral recognition polymer and its use to separate enantiomers". United States. https://www.osti.gov/servlets/purl/1531438.
@article{osti_1531438,
title = {Chiral recognition polymer and its use to separate enantiomers},
author = {Kaner, Richard B. and Knobler, Charles M. and Guo, Hailan},
abstractNote = {A new polymeric material, a process for forming the material and method of using the material to separate enantiomers of chiral compounds, particularly amino acids and pharmaceuticals are disclosed. A polymeric material can be formed from polyaniline doped with a chiral acid and then extracted with a suitable base. This leaves behind a polymeric material which preferentially traps, and then selectively releases, one enantiomer of a chiral mixture brought in contact with the surface of the polymeric material. In particular, when polyaniline is doped with either R- or S-camphorsulfonic acid (CSA) it takes on a chiral structure. Removing the chiral acid dopant leads to a new chiral polyaniline. The dedoped chiral polyanilines have the ability to discriminate among enantiomers of many compounds which exist in chiral mixtures.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2001},
month = {7}
}

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Works referenced in this record:

Membranes having selective permeability
patent, March 1992


Polyaniline, a novel conducting polymer. Morphology and chemistry of its oxidation and reduction in aqueous electrolytes
journal, January 1986

  • Huang, Wu-Song; Humphrey, Brian D.; MacDiarmid, Alan G.
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Method for membrane reactor resolution of stereoisomers
patent, December 1991


A chiral recognition polymer based on polyaniline
journal, May 1999


Large induced optical activity in the conduction band of polyaniline doped with (1S)-(+)-10-camphorsulfonic acid
journal, September 1994


Facile synthesis of optically active polyaniline and polytoluidine
journal, January 1996


Conjugated Polymer Films for Gas Separations
journal, June 1991


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