An in depth study of solvent effects on yield and average molecular weight in poly(3-hexylthiophene)

Poly(3-hexylthiophene) was synthesized by chemical oxidation using FeCl3 in chloroform, dichloromethane, acetonitrile, nitromethane, nitrobenzene and mixtures of these solvents. Comparative reactions for 1 day at room temperature were carried out to investigate solvent effects. Polymer samples and t...

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Bibliographic Details
Published in:Polymer (Guilford) 2017-04, Vol.115, p.21-27
Main Authors: Gadient, Jennifer, Groch, Rebecca, Lind, Cora
Format: Article
Language:English
Subjects:
Acetonitrile
Chemical synthesis
Chloroform
Correlation analysis
Dichloromethane
MALDI
Molecular weight
Nitrobenzene
Nitromethane
Oxidation
Oxidation potential
Oxidative polymerization
Poly(3-hexylthiophene)
Polymers
Solvent effect
Solvents
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Summary:Poly(3-hexylthiophene) was synthesized by chemical oxidation using FeCl3 in chloroform, dichloromethane, acetonitrile, nitromethane, nitrobenzene and mixtures of these solvents. Comparative reactions for 1 day at room temperature were carried out to investigate solvent effects. Polymer samples and the remaining reaction solutions were analyzed by MALDI-MS and LDI-MS to determine Mw and reaction completeness, respectively. Solubilities of FeCl3, FeCl2, and P3HT in each pure solvent were measured and correlated to the results. Open circuit potentials of FeCl3 and mixtures of FeCl3 and FeCl2 in pure solvents were measured and compared to the experimentally determined oxidation potential of 3-hexylthiophene. An optimized solvent system for reproducible synthesis of high Mw P3HT with quantitative yields is proposed based on MS analysis results. [Display omitted] •Solubilities of P3HT and FeCl2 significantly affect the final product.•CHCl3 gives high yields but irreproducible Mw.•CH2Cl2-nitrobenzene gave high yield, high Mw and excellent reproducibility.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2017.03.014