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WO1997005631A1 - Dendrimeres electroconducteurs - Google Patents

Dendrimeres electroconducteurs Download PDF

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Publication number
WO1997005631A1
WO1997005631A1 PCT/US1996/012183 US9612183W WO9705631A1 WO 1997005631 A1 WO1997005631 A1 WO 1997005631A1 US 9612183 W US9612183 W US 9612183W WO 9705631 A1 WO9705631 A1 WO 9705631A1
Authority
WO
WIPO (PCT)
Prior art keywords
electrophoric
dendrimer
compound
electrically conductive
reaction product
Prior art date
Application number
PCT/US1996/012183
Other languages
English (en)
Inventor
Larry L. Miller
Donald A. Tomalia
Robert G. Duan
Original Assignee
Dendritech, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dendritech, Inc. filed Critical Dendritech, Inc.
Priority to EP96926124A priority Critical patent/EP0840932A4/fr
Priority to US09/000,311 priority patent/US6043336A/en
Priority to AU66374/96A priority patent/AU6637496A/en
Publication of WO1997005631A1 publication Critical patent/WO1997005631A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/003—Dendrimers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/121—Charge-transfer complexes

Definitions

  • U.S. Patent 5,272,217 discloses a polymeric complex comprised of a quaternized cationic polyamine which is combined with N,N-bis(4,-hydroxysulfonylphen-l'-yl)-l, 4,5,8- naphthalenetetracarboxylic acid diimide disodium salt.
  • the complex is precipitated as a solid or deposited as a film by electro-precipitation.
  • the resulting complex exhibits highly anisotropic electrical conductivity which is generally several orders of magnitude lower than that of doped polyacetylene.
  • the reactive sites are unsymmetrically located on a given branch, e.g., one might be located along the length of the branch while another might be located at the end of the branch.
  • dendrimers as used herein is intended to include dendrons.
  • a dendron is a species of dendrimer having branches emanating from a focal point which is or can be joined to a core, either directly or through a linking moiety.
  • An ammonia core dendrimer might be thought of as an ammonia molecule having 3 dendrons radiating from the core.
  • the ratio of excess ethylenediamine to methyl carboxylate moieties is preferably from about 2:1 to about 120:1.
  • the zero generation adduct is then reacted with excess methyl acrylate under Michael's addition conditions to form a second generation adduct having terminal methyl ester moieties, which are subsequently reacted with excess ethylenediamine under amide forming conditions to produce a polyamidoamine dendrimer having ordered, first generation dendritic branches with terminal amine moieties.
  • the excess of co-reactant to reactive moieties is preferably from about 2:1 to about 120:1.
  • R is as follows:
  • the dendrimer and the chosen electrophore are chemically reacted to covalently bond the electrophore to the terminal functional groups on the dendrimer.
  • the resulting peripherally modified dendrimer has electrophoric moieties which can be reduced in a polar solvent to form anion radical groups which aggregate into ⁇ -stacks which can form electrically conductive pathways.
  • a polyamidoamine dendrimer can be reacted with a naphthalene diimide having the above formula I to form a dendrimer having the following structure:
  • the resulting peripherally modified dendrimers are contacted with a reducing agent to convert the terminally bonded electrophore into anion radical groups which form ⁇ -stacks in polar solutions.
  • a reducing agent to reduce the terminal electrophoric moieties to form anion moieties.
  • suitable and appropriate reducing agents is well within the ability of those having ordinary skill in the art.
  • a preferred reducing agent is a ⁇ , which can be utilized in varying amounts depending upon electric conductivity and other properties which are desired.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Polymère électroconducteur constitué d'un produit de réaction d'un dendrimère et d'un composé électrophorétique qui présente un empilage en pi lors d'une réduction. Le produit de réaction qui est un dendrimère modifié en périphérie est formé puis réduit, soit chimiquement soit électrochimiquement, dans un solvant polaire. Les fractions électrophorétique réduites s'aggrègent (formes des piles en π) pour donner des cheminements électriquement conducteurs. Les dendrimères modifiés en périphérie et réduits visés de cette invention peuvent être moulés sous la forme de films et sous d'autres formes solides pour produire des conducteurs électriques et des semi-conducteurs souples. Les polymères conducteurs de cette invention présentent des conductivités électriques comparables à celle d'un polyacétylène dopé, mais sont résistants à l'oxygène et à l'humidité.
PCT/US1996/012183 1995-07-26 1996-07-25 Dendrimeres electroconducteurs WO1997005631A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP96926124A EP0840932A4 (fr) 1995-07-26 1996-07-25 Dendrimeres electroconducteurs
US09/000,311 US6043336A (en) 1996-07-25 1996-07-25 Electrically conducting dendrimers
AU66374/96A AU6637496A (en) 1995-07-26 1996-07-25 Electrically conducting dendrimers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US153795P 1995-07-26 1995-07-26
US60/001,537 1995-07-26
US525795P 1995-10-13 1995-10-13
US60/005,527 1995-10-13

Publications (1)

Publication Number Publication Date
WO1997005631A1 true WO1997005631A1 (fr) 1997-02-13

Family

ID=26669171

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/012183 WO1997005631A1 (fr) 1995-07-26 1996-07-25 Dendrimeres electroconducteurs

Country Status (3)

Country Link
EP (1) EP0840932A4 (fr)
AU (1) AU6637496A (fr)
WO (1) WO1997005631A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010006698A1 (fr) * 2008-06-30 2010-01-21 Eni S.P.A. Copolymères conjugués de faible bande d'énergie interdite et leur procédé de fabrication

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4558120A (en) * 1983-01-07 1985-12-10 The Dow Chemical Company Dense star polymer
US5272217A (en) * 1992-03-12 1993-12-21 Regents Of The University Of Minnesota Anisotropic polymers
EP0682059A1 (fr) * 1994-05-13 1995-11-15 Gould Electronics Inc. Electrolytes polymères ayant une structure dendrimère
US5520904A (en) * 1995-01-27 1996-05-28 Mallinckrodt Medical, Inc. Calcium/oxyanion-containing particles with a polymerical alkoxy coating for use in medical diagnostic imaging
US5527524A (en) * 1986-08-18 1996-06-18 The Dow Chemical Company Dense star polymer conjugates
US5530092A (en) * 1992-01-13 1996-06-25 Dsm N.V. Dendritic macromolecule and the preparation thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4558120A (en) * 1983-01-07 1985-12-10 The Dow Chemical Company Dense star polymer
US5527524A (en) * 1986-08-18 1996-06-18 The Dow Chemical Company Dense star polymer conjugates
US5530092A (en) * 1992-01-13 1996-06-25 Dsm N.V. Dendritic macromolecule and the preparation thereof
US5272217A (en) * 1992-03-12 1993-12-21 Regents Of The University Of Minnesota Anisotropic polymers
EP0682059A1 (fr) * 1994-05-13 1995-11-15 Gould Electronics Inc. Electrolytes polymères ayant une structure dendrimère
US5520904A (en) * 1995-01-27 1996-05-28 Mallinckrodt Medical, Inc. Calcium/oxyanion-containing particles with a polymerical alkoxy coating for use in medical diagnostic imaging

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0840932A4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010006698A1 (fr) * 2008-06-30 2010-01-21 Eni S.P.A. Copolymères conjugués de faible bande d'énergie interdite et leur procédé de fabrication

Also Published As

Publication number Publication date
AU6637496A (en) 1997-02-26
EP0840932A4 (fr) 1998-08-12
EP0840932A1 (fr) 1998-05-13

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