Synthesis, photophysical and photovoltaic properties of conjugated polymers containing fused donor-acceptor dithienopyrrolobenzothiadiazole and dithienopyrroloquinoxaline arenes

Yen-Ju Cheng; Yu Ju Ho; Chiu Hsiang Chen; Wei Shun Kao; Cheng En Wu; So Lin Hsu; Chain-Shu Hsu

doi:10.1021/ma202764v

Synthesis, photophysical and photovoltaic properties of conjugated polymers containing fused donor-acceptor dithienopyrrolobenzothiadiazole and dithienopyrroloquinoxaline arenes

Yen-Ju Cheng^*, Yu Ju Ho, Chiu Hsiang Chen, Wei Shun Kao, Cheng En Wu, So Lin Hsu, Chain-Shu Hsu

^*Corresponding author for this work

Department of Applied Chemistry

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

68 Scopus citations

Abstract

We have developed two nitrogen-bridged pentacyclic donor-acceptor dithienopyrrolobenzothiadiazole (DTPBT) and dithienopyrroloquinoxaline (DTPQX) arenes where the two outer electron-rich thiophene moieties are covalently fastened with the central electron-deficient benzothiadiazole and quinoxaline cores by two nitrogen bridges. These rigid and coplanar DTPBT and DTPQX building blocks were copolymerized with fluorene (F), carbazole (C) and cyclopentadithiophene (CPDT) units via Suzuki or Stille coupling polymerization to afford six new alternating copolymers PFDTPBT, PCDTPBT, PCPDTDTPBT, PFDTPQX, PCDTPQX and PCPDTDTPQX, respectively. The nitrogen bridges not only planarize the structure to induce stronger intermolecular π-π interaction but also play an important role in determining the electronic and photophysical properties of the polymers. The device based on PFDTPQX/PC ₇₁BM (1:4, w/w) exhibited a open-circuit voltage (V _oc) of 0.72 V, a short-circuit current (J _sc) of 8.62 mA/cm ² and a FF of 0.55 leading to a decent power conversion efficiency (PCE) of 3.40% due to the lower-lying HOMO energy level, and the highest hole-mobility of PFDTPQX.

Original language	English
Pages (from-to)	2690-2698
Number of pages	9
Journal	Macromolecules
Volume	45
Issue number	6
DOIs	https://doi.org/10.1021/ma202764v
State	Published - 27 Mar 2012

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@article{2da9aca085f44e93b781fb27ac060292,

title = "Synthesis, photophysical and photovoltaic properties of conjugated polymers containing fused donor-acceptor dithienopyrrolobenzothiadiazole and dithienopyrroloquinoxaline arenes",

abstract = "We have developed two nitrogen-bridged pentacyclic donor-acceptor dithienopyrrolobenzothiadiazole (DTPBT) and dithienopyrroloquinoxaline (DTPQX) arenes where the two outer electron-rich thiophene moieties are covalently fastened with the central electron-deficient benzothiadiazole and quinoxaline cores by two nitrogen bridges. These rigid and coplanar DTPBT and DTPQX building blocks were copolymerized with fluorene (F), carbazole (C) and cyclopentadithiophene (CPDT) units via Suzuki or Stille coupling polymerization to afford six new alternating copolymers PFDTPBT, PCDTPBT, PCPDTDTPBT, PFDTPQX, PCDTPQX and PCPDTDTPQX, respectively. The nitrogen bridges not only planarize the structure to induce stronger intermolecular π-π interaction but also play an important role in determining the electronic and photophysical properties of the polymers. The device based on PFDTPQX/PC 71BM (1:4, w/w) exhibited a open-circuit voltage (V oc) of 0.72 V, a short-circuit current (J sc) of 8.62 mA/cm 2 and a FF of 0.55 leading to a decent power conversion efficiency (PCE) of 3.40% due to the lower-lying HOMO energy level, and the highest hole-mobility of PFDTPQX.",

author = "Yen-Ju Cheng and Ho, {Yu Ju} and Chen, {Chiu Hsiang} and Kao, {Wei Shun} and Wu, {Cheng En} and Hsu, {So Lin} and Chain-Shu Hsu",

year = "2012",

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doi = "10.1021/ma202764v",

language = "English",

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AU - Cheng, Yen-Ju

AU - Ho, Yu Ju

AU - Chen, Chiu Hsiang

AU - Kao, Wei Shun

AU - Wu, Cheng En

AU - Hsu, So Lin

AU - Hsu, Chain-Shu

PY - 2012/3/27

Y1 - 2012/3/27

N2 - We have developed two nitrogen-bridged pentacyclic donor-acceptor dithienopyrrolobenzothiadiazole (DTPBT) and dithienopyrroloquinoxaline (DTPQX) arenes where the two outer electron-rich thiophene moieties are covalently fastened with the central electron-deficient benzothiadiazole and quinoxaline cores by two nitrogen bridges. These rigid and coplanar DTPBT and DTPQX building blocks were copolymerized with fluorene (F), carbazole (C) and cyclopentadithiophene (CPDT) units via Suzuki or Stille coupling polymerization to afford six new alternating copolymers PFDTPBT, PCDTPBT, PCPDTDTPBT, PFDTPQX, PCDTPQX and PCPDTDTPQX, respectively. The nitrogen bridges not only planarize the structure to induce stronger intermolecular π-π interaction but also play an important role in determining the electronic and photophysical properties of the polymers. The device based on PFDTPQX/PC 71BM (1:4, w/w) exhibited a open-circuit voltage (V oc) of 0.72 V, a short-circuit current (J sc) of 8.62 mA/cm 2 and a FF of 0.55 leading to a decent power conversion efficiency (PCE) of 3.40% due to the lower-lying HOMO energy level, and the highest hole-mobility of PFDTPQX.

AB - We have developed two nitrogen-bridged pentacyclic donor-acceptor dithienopyrrolobenzothiadiazole (DTPBT) and dithienopyrroloquinoxaline (DTPQX) arenes where the two outer electron-rich thiophene moieties are covalently fastened with the central electron-deficient benzothiadiazole and quinoxaline cores by two nitrogen bridges. These rigid and coplanar DTPBT and DTPQX building blocks were copolymerized with fluorene (F), carbazole (C) and cyclopentadithiophene (CPDT) units via Suzuki or Stille coupling polymerization to afford six new alternating copolymers PFDTPBT, PCDTPBT, PCPDTDTPBT, PFDTPQX, PCDTPQX and PCPDTDTPQX, respectively. The nitrogen bridges not only planarize the structure to induce stronger intermolecular π-π interaction but also play an important role in determining the electronic and photophysical properties of the polymers. The device based on PFDTPQX/PC 71BM (1:4, w/w) exhibited a open-circuit voltage (V oc) of 0.72 V, a short-circuit current (J sc) of 8.62 mA/cm 2 and a FF of 0.55 leading to a decent power conversion efficiency (PCE) of 3.40% due to the lower-lying HOMO energy level, and the highest hole-mobility of PFDTPQX.

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ER -

Synthesis, photophysical and photovoltaic properties of conjugated polymers containing fused donor-acceptor dithienopyrrolobenzothiadiazole and dithienopyrroloquinoxaline arenes

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