Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air

Zhuping Fei; Xiang Gao; Jeremy Smith; Pichaya Pattanasattayavong; Ester Buchaca Domingo; Natalie Stingelin; Scott E. Watkins; Thomas D. Anthopoulos; R. Joseph Kline; Martin Heeney

doi:10.1021/cm303166z

Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air

Zhuping Fei, Xiang Gao, Jeremy Smith, Pichaya Pattanasattayavong, Ester Buchaca Domingo, Natalie Stingelin, Scott E. Watkins, Thomas D. Anthopoulos, R. Joseph Kline, Martin Heeney^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

We report the synthesis of two novel cyclopenta[2,1-b:3,4-b′] dithiophen-4-one monomers containing solubilizing alkyl groups in the peripheral 3,5 positions. Polymerization with (E)-1,2-bis(tributylstannyl)-ethylene under Stille coupling conditions afforded the first reported examples of soluble poly(cyclopentadithiophen-4-one)vinylenes. The resulting polymers absorb in the near-infrared, with a maximum thin film absorbance around 815 nm and have optical band gaps of 1.25 eV. The polymers exhibit promising ambipolar field effect transistor performance, with average saturated mobilities of 0.5 cm ² V^-1 s^-1 for holes and 0.12 cm ²V^-1 s^-1 for electrons. The ambipolar transistors operate in both the hole and electron transport regimes in ambient air. Prolonged exposure to ambient atmosphere leads to a gradual loss of the electron transport behavior, with little change observed in the p-type mobility.

Original language	English (US)
Pages (from-to)	59-68
Number of pages	10
Journal	Chemistry of Materials
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/cm303166z
State	Published - Jan 8 2013
Externally published	Yes

Keywords

conjugated polymers
low band gap polymer
near-infrared absorbers
polymer field effect transistors
structure-property relationships

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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10.1021/cm303166z

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Fei, Z., Gao, X., Smith, J., Pattanasattayavong, P., Buchaca Domingo, E., Stingelin, N., Watkins, S. E., Anthopoulos, T. D., Kline, R. J., & Heeney, M. (2013). Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air. Chemistry of Materials, 25(1), 59-68. https://doi.org/10.1021/cm303166z

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title = "Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air",

abstract = "We report the synthesis of two novel cyclopenta[2,1-b:3,4-b′] dithiophen-4-one monomers containing solubilizing alkyl groups in the peripheral 3,5 positions. Polymerization with (E)-1,2-bis(tributylstannyl)-ethylene under Stille coupling conditions afforded the first reported examples of soluble poly(cyclopentadithiophen-4-one)vinylenes. The resulting polymers absorb in the near-infrared, with a maximum thin film absorbance around 815 nm and have optical band gaps of 1.25 eV. The polymers exhibit promising ambipolar field effect transistor performance, with average saturated mobilities of 0.5 cm 2 V-1 s-1 for holes and 0.12 cm 2V-1 s-1 for electrons. The ambipolar transistors operate in both the hole and electron transport regimes in ambient air. Prolonged exposure to ambient atmosphere leads to a gradual loss of the electron transport behavior, with little change observed in the p-type mobility.",

keywords = "conjugated polymers, low band gap polymer, near-infrared absorbers, polymer field effect transistors, structure-property relationships",

author = "Zhuping Fei and Xiang Gao and Jeremy Smith and Pichaya Pattanasattayavong and {Buchaca Domingo}, Ester and Natalie Stingelin and Watkins, {Scott E.} and Anthopoulos, {Thomas D.} and Kline, {R. Joseph} and Martin Heeney",

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doi = "10.1021/cm303166z",

language = "English (US)",

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Fei, Z, Gao, X, Smith, J, Pattanasattayavong, P, Buchaca Domingo, E, Stingelin, N, Watkins, SE, Anthopoulos, TD, Kline, RJ & Heeney, M 2013, 'Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air', Chemistry of Materials, vol. 25, no. 1, pp. 59-68. https://doi.org/10.1021/cm303166z

TY - JOUR

T1 - Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air

AU - Fei, Zhuping

AU - Gao, Xiang

AU - Smith, Jeremy

AU - Pattanasattayavong, Pichaya

AU - Buchaca Domingo, Ester

AU - Stingelin, Natalie

AU - Watkins, Scott E.

AU - Anthopoulos, Thomas D.

AU - Kline, R. Joseph

AU - Heeney, Martin

PY - 2013/1/8

Y1 - 2013/1/8

N2 - We report the synthesis of two novel cyclopenta[2,1-b:3,4-b′] dithiophen-4-one monomers containing solubilizing alkyl groups in the peripheral 3,5 positions. Polymerization with (E)-1,2-bis(tributylstannyl)-ethylene under Stille coupling conditions afforded the first reported examples of soluble poly(cyclopentadithiophen-4-one)vinylenes. The resulting polymers absorb in the near-infrared, with a maximum thin film absorbance around 815 nm and have optical band gaps of 1.25 eV. The polymers exhibit promising ambipolar field effect transistor performance, with average saturated mobilities of 0.5 cm 2 V-1 s-1 for holes and 0.12 cm 2V-1 s-1 for electrons. The ambipolar transistors operate in both the hole and electron transport regimes in ambient air. Prolonged exposure to ambient atmosphere leads to a gradual loss of the electron transport behavior, with little change observed in the p-type mobility.

AB - We report the synthesis of two novel cyclopenta[2,1-b:3,4-b′] dithiophen-4-one monomers containing solubilizing alkyl groups in the peripheral 3,5 positions. Polymerization with (E)-1,2-bis(tributylstannyl)-ethylene under Stille coupling conditions afforded the first reported examples of soluble poly(cyclopentadithiophen-4-one)vinylenes. The resulting polymers absorb in the near-infrared, with a maximum thin film absorbance around 815 nm and have optical band gaps of 1.25 eV. The polymers exhibit promising ambipolar field effect transistor performance, with average saturated mobilities of 0.5 cm 2 V-1 s-1 for holes and 0.12 cm 2V-1 s-1 for electrons. The ambipolar transistors operate in both the hole and electron transport regimes in ambient air. Prolonged exposure to ambient atmosphere leads to a gradual loss of the electron transport behavior, with little change observed in the p-type mobility.

KW - conjugated polymers

KW - low band gap polymer

KW - near-infrared absorbers

KW - polymer field effect transistors

KW - structure-property relationships

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Near infrared absorbing soluble poly(cyclopenta[2,1-b:3,4-b′] dithiophen-4-one)vinylene polymers exhibiting high hole and electron mobilities in ambient air

Abstract

Keywords

ASJC Scopus subject areas

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