Issue 37, 2022

Statistical copolymers of thiophene-3-carboxylates and selenophene-3-carboxylates; 77Se NMR as a tool to examine copolymer sequence in selenophene-based conjugated polymers

Abstract

Herein, we demonstrate that homopolymerization and statistical copolymerization of 2-ethylhexyl thiophene-3-carboxylate and 2-ethylhexyl selenophene-3-carboxylate monomers is possible via Suzuki–Miyaura cross-coupling. A commercially available palladium catalyst ([1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)dichloropalladium(II) or PEPPSI-IPent) was employed to prepare regioregular conjugated polymers with high molecular weights (∼20–30 kg mol−1), and relatively narrow molecular weight distributions. The optical bandgap in the copolymer series could be reduced by increasing the concentration of selenophene-3-carboxylate in the material. Configurational triads were observed in the 1H NMR spectra of the statistical copolymers, which were assigned using a combination of 2D NMR techniques. The use of a 1H–77Se HSQC spectrum to further examine sequence distribution in the statistical copolymers revealed how 77Se NMR can be used as a tool to examine the microstructure of Se-containing conjugated polymers.

Graphical abstract: Statistical copolymers of thiophene-3-carboxylates and selenophene-3-carboxylates; 77Se NMR as a tool to examine copolymer sequence in selenophene-based conjugated polymers

Supplementary files

Article information

Article type
Paper
Submitted
16 Jun 2022
Accepted
08 Aga 2022
First published
09 Aga 2022

Polym. Chem., 2022,13, 5316-5324

Author version available

Statistical copolymers of thiophene-3-carboxylates and selenophene-3-carboxylates; 77Se NMR as a tool to examine copolymer sequence in selenophene-based conjugated polymers

M. Kawakami, K. H. G. Schulz, A. J. Varni, C. F. Tormena, R. R. Gil and K. J. T. Noonan, Polym. Chem., 2022, 13, 5316 DOI: 10.1039/D2PY00777K

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