skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Accessing conjugated polymers with precisely controlled heterobisfunctional chain ends via post-polymerization modification of the OTf group and controlled Pd(0)/t-Bu3P-catalyzed Suzuki cross-coupling polymerization

Journal Article · · ChemComm
DOI:https://doi.org/10.1039/C5CC06188A· OSTI ID:1245348
 [1];  [2];  [1]
  1. College of Staten Island and the Graduate Center of the City Univ. of New York, Staten Island, NY (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

In this study, a general strategy toward the synthesis of well-defined conjugated polymers with controlled heterobisfunctional chain ends via combination of controlled Pd(0)/t-Bu3P Suzuki cross-coupling polymerization with the post-polymerization modification of the triflate (OTf) group was disclosed.

Research Organization:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC05-00OR22725
OSTI ID:
1245348
Journal Information:
ChemComm, Vol. 51, Issue 80; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 14 works
Citation information provided by
Web of Science

References (46)

Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices journal March 2009
Synthesis of Conjugated Polymers for Organic Solar Cell Applications journal November 2009
π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications journal February 2011
Designing π-conjugated polymers for organic electronics journal December 2013
The future of organic photovoltaics journal January 2015
Poly(3-hexylthiophene)−CdSe Quantum Dot Bulk Heterojunction Solar Cells: Influence of the Functional End-Group of the Polymer journal June 2009
Effect of End Groups on Optoelectronic Properties of Poly(9,9-dioctylfluorene): A Study with Hexadecylfluorenes as Model Polymers journal October 2012
Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance journal December 2012
Exploring the synthesis and impact of end-functional poly(3-hexylthiophene) journal February 2015
Tuning the Electrical Conductivity and Self-Assembly of Regioregular Polythiophene by Block Copolymerization: Nanowire Morphologies in New Di- and Triblock Copolymers We gratefully acknowledge support from the NSF (CHE-9807707). journal January 2002
Facile Synthesis of Well-Defined Block Copolymers Containing Regioregular Poly(3-hexyl thiophene) via Anionic Macroinitiation Method and Their Self-Assembly Behavior journal September 2007
Facile Synthesis of Well-Defined Coil−Rod−Coil Block Copolymer Composed of Regioregular Poly(3-hexylthiophene) via Anionic Coupling Reaction journal February 2010
Synthesis and Characterization of Monocarboxylated Poly(3-hexylthiophene)s via Quantitative End-Group Functionalization journal September 2010
Mimicking Conjugated Polymer Thin-Film Photophysics with a Well-Defined Triblock Copolymer in Solution journal February 2012
Conductive Polymer Brushes of Regioregular Head-to-Tail Poly(3-alkylthiophenes) via Catalyst-Transfer Surface-Initiated Polycondensation journal May 2007
Grafting of Polyfluorene by Surface-Initiated Suzuki Polycondensation journal March 2009
Design of Well-Defined Monofunctionalized Poly(3-hexylthiophene)s: Toward the Synthesis of Semiconducting Graft Copolymers journal February 2012
Organic−Inorganic Nanocomposites via Directly Grafting Conjugated Polymers onto Quantum Dots journal October 2007
End-Group Functionalization of Poly(3-hexylthiophene) as an Efficient Route to Photosensitize Nanocrystalline TiO 2 Films for Photovoltaic Applications journal May 2011
Constructing Regioregular Star Poly(3-hexylthiophene) via Externally Initiated Kumada Catalyst-Transfer Polycondensation journal February 2012
Facile synthesis for well-defined A 2 B miktoarm star copolymer of poly(3-hexylthiophene) and poly(methyl methacrylate) by the combination of anionic polymerization and click reaction journal February 2013
Conducting Polymer/SWCNTs Modular Hybrid Materials via Diels–Alder Ligation journal March 2013
Conjugated Star Polymers from Multidirectional Suzuki–Miyaura Polymerization for Live Cell Imaging journal January 2015
Conjugated Polymer Synthesis via Catalyst-Transfer Polycondensation (CTP): Mechanism, Scope, and Applications journal September 2013
Scope of controlled synthesis via chain-growth condensation polymerization: from aromatic polyamides to π-conjugated polymers journal January 2013
In Situ Hetero End-Functionalized Polythiophene and Subsequent “Click” Chemistry With DNA journal February 2012
Synthesis and Photophysics of Fully π-Conjugated Heterobis-Functionalized Polymeric Molecular Wires via Suzuki Chain-Growth Polymerization journal October 2012
Enhanced Brightness Emission-Tuned Nanoparticles from Heterodifunctional Polyfluorene Building Blocks journal January 2013
Carbon−Carbon Bond-Forming Reductive Elimination from Arylpalladium Complexes Containing Functionalized Alkyl Groups. Influence of Ligand Steric and Electronic Properties on Structure, Stability, and Reactivity journal July 2004
Chain-Growth Polymerization for the Synthesis of Polyfluorene via Suzuki−Miyaura Coupling Reaction from an Externally Added Initiator Unit journal June 2007
Externally Initiated Regioregular P3HT with Controlled Molecular Weight and Narrow Polydispersity journal September 2009
Steric Effects of the Initiator Substituent Position on the Externally Initiated Polymerization of 2-Bromo-5-iodo-3-hexylthiophene journal February 2011
Effect of Initiators on the Kumada Catalyst-Transfer Polycondensation Reaction journal October 2009
Incorporation of Different End Groups in Conjugated Polymers Using Functional Nickel Initiators journal October 2009
Controlled Pd(0)/ t -Bu 3 P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with PhPd( t -Bu 3 P)I or Pd 2 (dba) 3 / t -Bu 3 P/ArI as the Initiator journal August 2012
Controlled Pd(0)/ t -Bu 3 P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with ArPd( t -Bu 3 P)X or Pd 2 (dba) 3 / t -Bu 3 P/ArX as the Initiator journal January 2015
End-group modification of regioregular poly(3-alkylthiophene)s journal January 2000
End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization journal December 2002
Facile Synthesis of End-Functionalized Regioregular Poly(3-alkylthiophene)s via Modified Grignard Metathesis Reaction journal December 2005
Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions journal May 2000
A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids journal October 2010
t -Bu 3 P-Coordinated 2-Phenylaniline-Based Palladacycle Complex as a Precatalyst for the Suzuki Cross-Coupling Polymerization of Aryl Dibromides with Aryldiboronic Acids journal December 2012
t Bu 3 P-Coordinated 2-Phenylaniline-Based Palladacycle Complexes as Precatalyst for Pd-Catalyzed Coupling Reactions of Aryl Halides with Polyfluoroarenes by a C-H Activation Strategy : Pd-Catalyzed Coupling of Aryl Halides with Polyfluoroarenes journal December 2013
“Green” Atom Transfer Radical Polymerization:  From Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials journal June 2007
Organocatalysis: Opportunities and Challenges for Polymer Synthesis journal March 2010
Synthesis and self-assembly of poly(3-hexylthiophene)-block-poly(acrylic acid) journal January 2011

Cited By (3)

Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross‐Coupling Reactions journal July 2019
A General and Air-tolerant Strategy to Conjugated Polymers within Seconds under Palladium(I) Dimer Catalysis text January 2019
A General and Air‐tolerant Strategy to Conjugated Polymers within Seconds under Palladium(I) Dimer Catalysis journal July 2019