Title: Method for preparing dioxyheterocycle-based electrochromic polymers

Abstract

A method for preparing a conjugated polymer involves a DHAP polymerization of a 3,4-dioxythiophene, 3,4-dioxyfuran, or 3,4-dioxypyrrole and, optionally, at least one second conjugated monomer in the presence of a Pd or Ni comprising catalyst, an aprotic solvent, a carboxylic acid at a temperature in excess of 120.degree. C. At least one of the monomers is substituted with hydrogen reactive functionalities and at least one of the monomers is substituted with a Cl, Br, and/or I. The polymerization can be carried out at temperature of 140.degree. C. or more, and the DHAP polymerization can be carried out without a phosphine ligand or a phase transfer agent. The resulting polymer can display dispersity less than 2 and have a degree of polymerization in excess of 10.

Inventors:

Reynolds, John R.; Estrada, Leandro; Deininger, James; Arroyave-Mondragon, Frank Antonio

Issue Date:

2017-10-17

Research Org.:

Univ. of Florida, Gainesville, FL (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1400247

Patent Number(s):

9790326

Application Number:

14/897,063

Assignee:

UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

Patent Classifications (CPCs):

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08G - MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

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C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08G - MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

C08G2261/1412 - Saturated aliphatic units
C08G2261/1424 - containing ether groups, including alkoxy
C08G2261/3223 - containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
C08G2261/3243 - containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
C08G2261/41 - Organometallic coupling reactions
C08G2261/54 - electrochromatic
C08G61/126 - {with a five-membered ring containing one sulfur atom in the ring}
C08G75/00 - Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
C08G75/06 - from cyclic thioethers
C08G75/32 - Polythiazoles

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

C09K11/00 - Luminescent, e.g. electroluminescent, chemiluminescent materials
C09K2211/1491 - containing other combinations of heteroatoms
C09K9/02 - Organic tenebrescent materials

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01B - CABLES

H01B1/00 - Conductors or conductive bodies characterised by the conductive materials
H01B1/127 - {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

Y02E10/549 - organic PV cells

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DOE Contract Number:  

FG02-03ER15484

Resource Type:

Patent

Resource Relation:

Patent File Date: 2014 Jun 18

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE