On the role of single regiodefects and polydispersity in regioregular poly(3-hexylthiophene): defect distribution, synthesis of defect-free chains, and a simple model for the determination of crystallinity

Journal of the American Chemical Society
Peter KohnMichael Sommer

Abstract

Identifying structure formation in semicrystalline conjugated polymers is the fundamental basis to understand electronic processes in these materials. Although correlations between physical properties, structure formation, and device parameters of regioregular, semicrystalline poly(3-hexylthiophene) (P3HT) have been established, it has remained difficult to disentangle the influence of regioregularity, polydispersity, and molecular weight. Here we show that the most commonly used synthetic protocol for the synthesis of P3HT, the living Kumada catalyst transfer polycondensation (KCTP) with Ni(dppp)Cl(2) as the catalyst, leads to regioregular chains with one single tail-to-tail (TT) defect distributed over the whole chain, in contrast to the hitherto assumed exclusive location at the chain end. NMR end-group analysis and simulations are used to quantify this effect. A series of entirely defect-free P3HT materials with different molecular weights is synthesized via new, soluble nickel initiators. Data on structure formation in defect-free P3HT, as elucidated by various calorimetric and scattering experiments, allow the development of a simple model for estimating the degree of crystallinity. We find very good agreement for predict...Continue Reading

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Citations

Apr 23, 2016·Journal of the American Chemical Society·Chia-Hua TsaiKevin J T Noonan
Jun 15, 2016·ACS Nano·Jan-Michael Y CarrilloS Michael Kilbey
Aug 3, 2016·ACS Nano·Florian LombeckMichael Sommer
Nov 12, 2015·Chemical Reviews·Tsutomu Yokozawa, Yoshihiro Ohta
Nov 5, 2016·Chemical Reviews·Jean-Rémi PouliotMario Leclerc
Nov 3, 2016·ACS Applied Materials & Interfaces·Jing CuiEsther Rebollar
Dec 28, 2016·ACS Applied Materials & Interfaces·Youngkwon KimBumjoon J Kim
Jan 27, 2017·Journal of the American Chemical Society·François GrenierMario Leclerc
Feb 24, 2015·Physical Chemistry Chemical Physics : PCCP·Ruslan P KurtaSouren Grigorian
Feb 28, 2018·Proceedings of the National Academy of Sciences of the United States of America·Dominic RaithelRichard Hildner
Oct 2, 2012·Angewandte Chemie·Khosrow RahimiGünter Reiter
Apr 5, 2014·Macromolecular Rapid Communications·Tomasz JaroszPrzemyslaw Ledwon
Apr 25, 2017·Advanced Science·Christian KästnerHarald Hoppe
Aug 16, 2013·Beilstein Journal of Organic Chemistry·Helga SeylerWallace Wing Ho Wong
May 20, 2021·Physical Chemistry Chemical Physics : PCCP·Tobias KochNikos L Doltsinis
Jul 20, 2021·Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices·Sophie GriggsIain McCulloch
Mar 14, 2013·Journal of the American Chemical Society·Kerr JohnsonRichard H Friend
Jun 12, 2020·Journal of Chemical Information and Modeling·Wesley K TatumChristine K Luscombe
Aug 21, 2013·Journal of the American Chemical Society·Felix Peter Vinzenz KochPaul Smith
Dec 10, 2016·Journal of the American Chemical Society·Alexander S DudnikTobin J Marks
Oct 30, 2020·The Journal of Physical Chemistry. B·Stien VertommenGuy Koeckelberghs

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