Electrically conductive electroactive functionalized conjugated

Details Electrically conductive electroactive functionalized conjugated Electrically conductive electroactive functionalized conjugated

1996-02-06

2000-08-01

Nutter, Nathan M.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

530402, 530403, 530405, 530409, 530810, 530812, 530815, 530816, 530817, 205149, 210656, 210660, 210690, 210692, 427 58, 436518, 436528, 436531, 436532, C08G 6112, G01N 2700

Patent

active

060968257

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

Conjugated polymers, such as polypyrroles, polythiophenes, polyanilines, polyphenylenes and derivatives thereof are known for their electroactive nature, which is widely described in review works such as the "Handbook of Organic Conducting Polymers" (T. J. Skotheim editor, Marcel Dekker, New York, 1986). These polymers are obtained in the form of a film on an electrode, in the form of self-supporting films or alternatively in the form of a composite when combined with a polycationic or polyanionic polymer and behave like organic electrodes, which charge up according to an anodic oxidation process, by insertion of ions from the electrolytic medium. This electrochemical process is reversible, the reduction leading to the expulsion of the ions from this conjugated polymer or from the electroactive composite.
A second generation of conjugated polymers was then described in the literature, obtained by the covalent grafting, on to the monomer units of the polymers, of functional groups capable of providing these electroactive conjugated polymers with an additional function. By way of example, electrocatalytic metal complexes were grafted on to the monomer units of the polypyrrole, specific complexing macrocycles were grafted on to the polypyrrole or polythiophene chains for the recognition of cations in an electrolytic medium, and chiral groups were grafted on to polythiophenes for the recognition of optically active anions. All of these routes of functionalization have also formed the subject of development procedures detailed in the literature (F. Garnier, Angew. Chemie, 1989, 101, 529; A. Deronzier, J. C. Moutet, Acc. Chem. Res. 1989, 22, 249; J. Roncali, Chem Rev., 1992, 92, 711).
In the last few years authors have become interested in the use of functionalized conductive polymers for the development of analyte scavengers, in particular for diagnostic purposes. However, as indicated in Patent Application EP 0,314,009, it was commonly accepted by the scientific community that pyrrole polymers substituted either on the nitrogen atom or directly on the carbon atoms of the pyrrole ring were not good candidates for the development of analyte scavengers, in particular on account of the loss of conductivity of said polymers when functional groups are introduced on to the heteroatomic ring. In order to overcome this problem, the authors of this patent application thus envisaged the use of 2,5-di(2-thienylpyrrole) polymers which were grafted in the 3-position of the pyrrole ring with a reactive moiety with which an organic molecule could become covalently bonded. It should, however, be noted that on account of the hydrophobicity of the thiophene rings, the polymers described cannot be conductive and electroactive in aqueous media and consequently do not appear to be suitable for the detection and/or characterization of an analyte in a biological sample (see J. Roncali et al., Chem. Comm., 1986, page 783 and G. Tourillon et al., Electronal. Chem., 161, 407, 1984).


SUMMARY OF THE INVENTION

It has now been discovered, entirely surprisingly and contrary to what was hitherto accepted by specialists, that the conductivity and electroactivity of polypyrroles are retained provided that a functional group is grafted in the 3- or 4-position on the pyrrole ring using a functionalizing agent which allows the intended function to be distanced from the pyrrole ring. An antiligand is covalently bonded to the free end of the functional group, without the abovementioned properties of the polymer being modified. Such functionalized polymers have to date never been described and have shown themselves to be entirely suitable as scavengers for a biological ligand. Moreover, polypyrroles prove to be advantageous polymers on account of their biocompatibility. Lastly, the polypyrroles thus functionalized make it possible to prepare electroactive and conductive polymers of considerable thickness (up to several millimeters thick), which thereby allows a great density of functional sites and proportionately impr

REFERENCES:
patent: 5149826 (1992-09-01), Delabouglise et al.
F. Garnier, "Functionalized Conducting Polymers-Towards Intelligent Materials", Advanced Materials, vol. 101, pp. 101, pp. 529-533, (1989).
A. Deronzier et al., "Functionalized Polyprroles, New Molecular Materials for Electrocatalysis and Related Applications", Acc. Chem. Rec., vol. 22, pp. 249-255, (1989).
J. Roncall, "Conjugated Poly(thiophenes): Synthesis, Functionalization, and Applications,", Chem. Rev. vol. 92, pp. 711-738, (1992).
J. Roncall et al., "Electroactive Conducting Composites from Poly(3-methylthiophene) and Poly(methylmethoerylate)", J. Chem. Soc., Chem. Commun., (1986).
G. Tourillon et al., "Electrochemical Doping of Polythiophene in Aqueous Medium", J. Electroanal Chem., vol. 161, pp. 407-414, (1984).
D. Delabouglise et al., "Chiral Metals: Amino Acid-Substituted Conducting Polypyrroles", Synthetic Metals, vol. 39, pp. 117-120, (1990).
P. Baauerle et al., "Synthesis and Properties of Cerboxy-Functionalized Poly(3-alkylthienylenes)", Advanced Materials, vol. 2, pp. 490-494, (1990).
I.M. Chaiken, "Molecular Interactions, Affinity Methods, and the Developing Synergism Between Affinity Chromatography and Biological Recongnition", Affinity Chromatography and Biological Recognition, pp. 3-6 (1983).
B.M. Dunn et al., "Application of Quantitative Affinity Chromatography to the Study of Protein-Ligand Interactions", Affinity Chromatography and Biological Recognition, pp. 93-102 (1983).
S. Avrameas et al, "Immunoassays Based on Specific Bio-Recognition", Affinity Chromatography and Biological Recognition, pp. 363-373 (1983).
J.M. Egly, "Nucleic-Acids and Related Compounds in Affinity Chromatography", Affinity Chromatography and Biological Recognition, pp. 447-453 (1983).
W. J. Feast, "Synthesis of Conducting Polymers", Handbook of Conducting Polymers, vol. 1, pp. 1-44 (1986).
A.F. Diaz et al., "Electochemical Synthesis of Conducting Polymers", Handbook of Conducting Polymers, vol. 1, pp. 81-115 (1986).
G.B. Street, "Polypyrrole from Powder to Plastics", Handbook of Conducting Polymers, vol. 1, pp. 265-291 (1986).
G.A. Kossmehl, "Semiconducting and Conduting Polymers with Aromatic and Heteroaromatic Units" Handbook of Conducting Polymers, pp. 351-403 (1986).
J.R. Ellis, "Commercial Applications of Intrinsically Conducting Polymers", Handbook of Conducting Polymers, vol. 1, pp. 489-499 (1986).
J.M. Pochan, "The Oxidative Stability of Dopable Polyenes", Handbook of Conducting Polymers, vol. 1, pp. 1383-1405 (1986).
M. Egholm et al., "Peptide Nucleic Acids (PNA) Oligonucleotide Analogues with an Achiral Peptide Backbone", J. Am. Chem. Soc., vol. 114, pp. 1895-1897 (1992).
J.R. Uren, "Affinity Chromatography of Proteolytic Enzymes", Biochimica Et Biophysicia Acta, vol. 236, pp. 67-73 (1971).

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