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Method for preparing dioxyheterocycle-based electrochromic polymers

Patent ·
OSTI ID:1400247
; ; ;
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.
Research Organization:
UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC., Gainesville, FL (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
FG02-03ER15484
Assignee:
UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
Patent Number(s):
9,790,326
Application Number:
14/897,063
OSTI ID:
1400247
Country of Publication:
United States
Language:
English

References (11)

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Palladium-Catalyzed Direct Arylation of Heteroaromatic Compounds: Improved Conditions Utilizing Controlled Microwave Heating journal October 2011
Synthesis of 4,4′-dinonyl-2,2′-bithiazole-based copolymers via Pd-catalyzed direct C–H arylation journal January 2012
Direct arylation polycondensation for the synthesis of bithiophene-based alternating copolymers journal January 2013
Semi-random P3HT analogs via direct arylation polymerization
  • Rudenko, Andrey E.; Wiley, Calvin A.; Stone, Shiloh M.
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 18, p. 3691-3697 https://doi.org/10.1002/pola.26175
journal June 2012
Detailed Optimization of Polycondensation Reaction via Direct C-H Arylation of Ethylenedioxythiophene journal October 2012
Manufacture and demonstration of organic photovoltaic-powered electrochromic displays using roll coating methods and printable electrolytes journal January 2012
Pd-Catalysed Direct Arylation Polymerisation for Synthesis of Low-Bandgap Conjugated Polymers and Photovoltaic Performance journal July 2012
Color Control in π-Conjugated Organic Polymers for Use in Electrochromic Devices journal January 2010
Tetrathiafulvalene (TTF)-Functionalized Thiophene Copolymerized with 3,3‴-Didodecylquaterthiophene: Synthesis, TTF Trapping Activity, and Response to Trinitrotoluene journal January 2013
Assessment of the Intermediacy of Arylpalladium Carboxylate Complexes in the Direct Arylation of Benzene: Evidence for C−H Bond Cleavage by “Ligandless” Species journal March 2011

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