Fluorination in thieno[3,4-C]pyrrole-4,6-dione copolymers leading to electron transport, high crystallinity and end-on alignment

T. Weller, M. Breunig, C. J. Mueller, E. Gann, C. R. McNeill, M. Thelakkat

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A series of copolymers based on thieno[3,4-c]pyrrole-4,6-dione and thiophene-phenyl-thiophene with varying degrees of fluorination on the phenyl unit was synthesized by Stille polycondensation. The influence of the degree of fluorination on the optical, thermal and electrochemical properties of these polymers is systematically studied. Additionally, the charge transport in organic field effect transistors (OFETs) as well as the thin film alignment are investigated. After thermal annealing the non-fluorinated as well as difluorinated polymers show ambipolar charge transport in OFETs. In contrast, tetrafluorination results in exclusively n-type behaviour with an electron mobility of 3.7 × 10-4 cm2 V-1 s-1. GIWAXS measurements of as-cast and annealed films reveal a very interesting structural alignment in thin films. All polymers show the rarely observed "end-on" orientation, where the polymer chains stand on the substrate. This may be explained by the low molecular weights of these polymers in relation to the film thickness. Fluorination does not influence the microstructural properties, only the propensity of crystallization is increased.

Original languageEnglish
Pages (from-to)7527-7534
Number of pages8
JournalJournal of Materials Chemistry C
Volume5
Issue number30
DOIs
Publication statusPublished - 14 Aug 2017

Cite this

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title = "Fluorination in thieno[3,4-C]pyrrole-4,6-dione copolymers leading to electron transport, high crystallinity and end-on alignment",
abstract = "A series of copolymers based on thieno[3,4-c]pyrrole-4,6-dione and thiophene-phenyl-thiophene with varying degrees of fluorination on the phenyl unit was synthesized by Stille polycondensation. The influence of the degree of fluorination on the optical, thermal and electrochemical properties of these polymers is systematically studied. Additionally, the charge transport in organic field effect transistors (OFETs) as well as the thin film alignment are investigated. After thermal annealing the non-fluorinated as well as difluorinated polymers show ambipolar charge transport in OFETs. In contrast, tetrafluorination results in exclusively n-type behaviour with an electron mobility of 3.7 × 10-4 cm2 V-1 s-1. GIWAXS measurements of as-cast and annealed films reveal a very interesting structural alignment in thin films. All polymers show the rarely observed {"}end-on{"} orientation, where the polymer chains stand on the substrate. This may be explained by the low molecular weights of these polymers in relation to the film thickness. Fluorination does not influence the microstructural properties, only the propensity of crystallization is increased.",
author = "T. Weller and M. Breunig and Mueller, {C. J.} and E. Gann and McNeill, {C. R.} and M. Thelakkat",
year = "2017",
month = "8",
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doi = "10.1039/c7tc01999h",
language = "English",
volume = "5",
pages = "7527--7534",
journal = "Journal of Materials Chemistry C",
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publisher = "The Royal Society of Chemistry",
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}

Fluorination in thieno[3,4-C]pyrrole-4,6-dione copolymers leading to electron transport, high crystallinity and end-on alignment. / Weller, T.; Breunig, M.; Mueller, C. J.; Gann, E.; McNeill, C. R.; Thelakkat, M.

In: Journal of Materials Chemistry C, Vol. 5, No. 30, 14.08.2017, p. 7527-7534.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Fluorination in thieno[3,4-C]pyrrole-4,6-dione copolymers leading to electron transport, high crystallinity and end-on alignment

AU - Weller, T.

AU - Breunig, M.

AU - Mueller, C. J.

AU - Gann, E.

AU - McNeill, C. R.

AU - Thelakkat, M.

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N2 - A series of copolymers based on thieno[3,4-c]pyrrole-4,6-dione and thiophene-phenyl-thiophene with varying degrees of fluorination on the phenyl unit was synthesized by Stille polycondensation. The influence of the degree of fluorination on the optical, thermal and electrochemical properties of these polymers is systematically studied. Additionally, the charge transport in organic field effect transistors (OFETs) as well as the thin film alignment are investigated. After thermal annealing the non-fluorinated as well as difluorinated polymers show ambipolar charge transport in OFETs. In contrast, tetrafluorination results in exclusively n-type behaviour with an electron mobility of 3.7 × 10-4 cm2 V-1 s-1. GIWAXS measurements of as-cast and annealed films reveal a very interesting structural alignment in thin films. All polymers show the rarely observed "end-on" orientation, where the polymer chains stand on the substrate. This may be explained by the low molecular weights of these polymers in relation to the film thickness. Fluorination does not influence the microstructural properties, only the propensity of crystallization is increased.

AB - A series of copolymers based on thieno[3,4-c]pyrrole-4,6-dione and thiophene-phenyl-thiophene with varying degrees of fluorination on the phenyl unit was synthesized by Stille polycondensation. The influence of the degree of fluorination on the optical, thermal and electrochemical properties of these polymers is systematically studied. Additionally, the charge transport in organic field effect transistors (OFETs) as well as the thin film alignment are investigated. After thermal annealing the non-fluorinated as well as difluorinated polymers show ambipolar charge transport in OFETs. In contrast, tetrafluorination results in exclusively n-type behaviour with an electron mobility of 3.7 × 10-4 cm2 V-1 s-1. GIWAXS measurements of as-cast and annealed films reveal a very interesting structural alignment in thin films. All polymers show the rarely observed "end-on" orientation, where the polymer chains stand on the substrate. This may be explained by the low molecular weights of these polymers in relation to the film thickness. Fluorination does not influence the microstructural properties, only the propensity of crystallization is increased.

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