A fast controlled synthesis of poly(p-phenyleneethynylene)s under transition-metal-free conditions
Authors:
- 8 March 2016
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Polymer Chemistry
- Vol. 7 (13) , 2323-2328
Abstract
A transition-metal-free polymerization of an AB-type monomer for the synthesis of well-defined poly(p-phenyleneethynylene)s is described. The polymerization of 1-pentafluorophenylethynyl-4-[(trimethylsilyl)ethynyl]benzene with a catalytic amount of tetrabutylammonium fluoride or potassium t-butoxide in the presence of cryptand[2.2.2] affords polymers within a few minutes. When monitoring the polymerization, the molecular weight as a function of monomer conversion shows a linear relationship, where the polydispersity indexes are around 1.6. The polymerization proceeds predominantly via intramolecular fluoride anion transfer to the polymer end. End capping of the active polymerization end is also demonstrated.Keywords
This publication has 73 references indexed in Scilit:
- Scope of controlled synthesis via chain-growth condensation polymerization: from aromatic polyamides to π-conjugated polymersChemical Communications, 2013
- Designing and Refining Ni(II)diimine Catalysts Toward the Controlled Synthesis of Electron-Deficient Conjugated PolymersJournal of the American Chemical Society, 2013
- Murahashi Coupling Polymerization: Nickel(II)–N-Heterocyclic Carbene Complex-Catalyzed Polycondensation of Organolithium Species of (Hetero)arenesJournal of the American Chemical Society, 2013
- Trimethylsilyl-Terminated Oligo(phenylene ethynylene)s: An Approach to Single-Molecule Junctions with Covalent Au–C σ-BondsJournal of the American Chemical Society, 2012
- Chain-Growth Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and π-Conjugated PolymersChemical Reviews, 2009
- Chemical Sensors Based on Amplifying Fluorescent Conjugated PolymersChemical Reviews, 2007
- Chain-Growth Polymerization for Poly(3-hexylthiophene) with a Defined Molecular Weight and a Low PolydispersityMacromolecules, 2004
- Novel Poly(arylene ether)s with Pendent Trifluoromethyl GroupsMacromolecules, 1999
- The preparation and properties of polyfluoro aromatic and heteroaromatic compoundsJournal of Fluorine Chemistry, 1997
- Are Single Molecular Wires Conducting?Science, 1996