Synthesis of Two-Dimensional Terbenzodithiophene-based Derivative by Palladium-catalyzed C─H Benzannulation and Its Donor–Acceptor Copolymers for Organic Photovoltaics

Fong Yi Cao; Yung Lung Chen; Yu Ying Lai; Yen-Ju Cheng

doi:10.1002/jccs.201700221

Synthesis of Two-Dimensional Terbenzodithiophene-based Derivative by Palladium-catalyzed C─H Benzannulation and Its Donor–Acceptor Copolymers for Organic Photovoltaics

Fong Yi Cao, Yung Lung Chen, Yu Ying Lai, Yen-Ju Cheng^*

^*Corresponding author for this work

1 Scopus citations

Abstract

A new two-dimensional tetrathienyl-TBDT (TBDT-4T) was synthesized by employing palladium-catalyzed C─H benzannulation between an iodobiaryl and 1,2-dithienylacetylene. The stannylated TBDT-4T was copolymerized with di(thiophenyl)difluorobenzothiadiazole (FBT) and fluorothienothiophene (FTT) monomers to yield PTBDT-FBT and PTBDT-FTT, which showed high decomposition temperatures (421 and 408°C) and deep-lying HOMO levels (−5.80 and −5.84 eV). The inverted solar cell device using PTBDT-FBT:PC₇₁BM (1:1 in wt%) blend showed a power conversion efficiency (PCE) of 4.16%, while the device using PTBDT-FTT:PC₇₁BM (1:2 in wt%) blend showed a PCE of 3.98%.

Original language	English
Pages (from-to)	133-140
Number of pages	8
Journal	Journal of the Chinese Chemical Society
Volume	65
Issue number	1
DOIs	https://doi.org/10.1002/jccs.201700221
State	Published - Jan 2018

Keywords

Ladder-type polymer
Palladium-catalyzed C─H arylation
Polymer solar cell
Two-dimensional structure

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title = "Synthesis of Two-Dimensional Terbenzodithiophene-based Derivative by Palladium-catalyzed C─H Benzannulation and Its Donor–Acceptor Copolymers for Organic Photovoltaics",

abstract = "A new two-dimensional tetrathienyl-TBDT (TBDT-4T) was synthesized by employing palladium-catalyzed C─H benzannulation between an iodobiaryl and 1,2-dithienylacetylene. The stannylated TBDT-4T was copolymerized with di(thiophenyl)difluorobenzothiadiazole (FBT) and fluorothienothiophene (FTT) monomers to yield PTBDT-FBT and PTBDT-FTT, which showed high decomposition temperatures (421 and 408°C) and deep-lying HOMO levels (−5.80 and −5.84 eV). The inverted solar cell device using PTBDT-FBT:PC71BM (1:1 in wt%) blend showed a power conversion efficiency (PCE) of 4.16%, while the device using PTBDT-FTT:PC71BM (1:2 in wt%) blend showed a PCE of 3.98%.",

keywords = "Ladder-type polymer, Palladium-catalyzed C─H arylation, Polymer solar cell, Two-dimensional structure",

author = "Cao, {Fong Yi} and Chen, {Yung Lung} and Lai, {Yu Ying} and Yen-Ju Cheng",

note = "Publisher Copyright: {\textcopyright} 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jan,

doi = "10.1002/jccs.201700221",

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T1 - Synthesis of Two-Dimensional Terbenzodithiophene-based Derivative by Palladium-catalyzed C─H Benzannulation and Its Donor–Acceptor Copolymers for Organic Photovoltaics

AU - Cao, Fong Yi

AU - Chen, Yung Lung

AU - Lai, Yu Ying

AU - Cheng, Yen-Ju

PY - 2018/1

Y1 - 2018/1

N2 - A new two-dimensional tetrathienyl-TBDT (TBDT-4T) was synthesized by employing palladium-catalyzed C─H benzannulation between an iodobiaryl and 1,2-dithienylacetylene. The stannylated TBDT-4T was copolymerized with di(thiophenyl)difluorobenzothiadiazole (FBT) and fluorothienothiophene (FTT) monomers to yield PTBDT-FBT and PTBDT-FTT, which showed high decomposition temperatures (421 and 408°C) and deep-lying HOMO levels (−5.80 and −5.84 eV). The inverted solar cell device using PTBDT-FBT:PC71BM (1:1 in wt%) blend showed a power conversion efficiency (PCE) of 4.16%, while the device using PTBDT-FTT:PC71BM (1:2 in wt%) blend showed a PCE of 3.98%.

AB - A new two-dimensional tetrathienyl-TBDT (TBDT-4T) was synthesized by employing palladium-catalyzed C─H benzannulation between an iodobiaryl and 1,2-dithienylacetylene. The stannylated TBDT-4T was copolymerized with di(thiophenyl)difluorobenzothiadiazole (FBT) and fluorothienothiophene (FTT) monomers to yield PTBDT-FBT and PTBDT-FTT, which showed high decomposition temperatures (421 and 408°C) and deep-lying HOMO levels (−5.80 and −5.84 eV). The inverted solar cell device using PTBDT-FBT:PC71BM (1:1 in wt%) blend showed a power conversion efficiency (PCE) of 4.16%, while the device using PTBDT-FTT:PC71BM (1:2 in wt%) blend showed a PCE of 3.98%.

KW - Ladder-type polymer

KW - Palladium-catalyzed C─H arylation

KW - Polymer solar cell

KW - Two-dimensional structure

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DO - 10.1002/jccs.201700221

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ER -

Synthesis of Two-Dimensional Terbenzodithiophene-based Derivative by Palladium-catalyzed C─H Benzannulation and Its Donor–Acceptor Copolymers for Organic Photovoltaics

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