Carboxylate-substituted polythiophenes for efficient fullerene-free polymer solar cells: the effect of chlorination on their properties

Qi Wang, Miaomiao Li (Corresponding author), Xiaowei Zhang, Yunpeng Qin, Junke Wang, Jidong Zhang, Jianhui Hou, René A.J. Janssen, Yanhou Geng (Corresponding author)

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

Uittreksel

Two new wide-bandgap polythiophenes, i.e., poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3-chloro-2,2′-bithiophene] (PDCBT-Cl) and poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3,3′-dichloro-2,2′-bithiophene] (PDCBT-2Cl) comprising 3-chloro-2,2′-bithiophene and 3,3′-dichloro-2,2′-bithiophene moieties, respectively, were synthesized for fullerene-free polymer solar cells (PSCs). For comparison, three other polymers based on [2,2′-bithiophene]-4,4′-dicarboxylate (DCBT), i.e., PDCBT, PDCBT-F, and PDCBT-2F with 2,2′-bithiophene, 3-fluoro-2,2′-bithiophene, and 3,3′-difluoro-2,2′-bithiophene as comonomers, respectively, were also prepared. PSC devices were fabricated with these polymers as donor materials and ITIC-Th1 as acceptor. The incorporation of chlorine (Cl) or fluorine (F) atoms into polymers both efficiently downshifted the highest occupied molecular orbital (HOMO) energy levels, leading to higher open-circuit voltage (Voc) in the PSCs. Owing to the proper phase-separated morphology with favorable molecular packing and miscibility, the device based on PDCBT-Cl:ITIC-Th1 exhibited efficient exciton dissociation and charge collection as well as weak charge recombination and thereby displayed the best power conversion efficiency (PCE) up to 12.38%. The devices based on other polymers showed inferior PCEs (8.14% for PDCBT, 10.85% for PDCBT-F, 8.48% for PDCBT-2F, and 6.94% for PDCBT-2Cl). The monomers that are used to make PDCBT-Cl can be synthesized in relatively large scale from commercial available chemicals. All these indicate that PDCBT-Cl is a promising donor material for the large area fabrication of high-performance fullerene-free PSCs.

TaalEngels
Pagina's4464-4474
Aantal pagina's11
TijdschriftMacromolecules
Volume52
Nummer van het tijdschrift12
DOI's
StatusGepubliceerd - 25 jun 2019

Vingerafdruk

Fullerenes
Chlorination
Chlorine
Polymers
Fluorine
Molecular orbitals
Open circuit voltage
Excitons
Electron energy levels
Conversion efficiency
Energy gap
Solubility
Monomers
polythiophene
Polymer solar cells
Fabrication
Atoms

Citeer dit

Wang, Qi ; Li, Miaomiao ; Zhang, Xiaowei ; Qin, Yunpeng ; Wang, Junke ; Zhang, Jidong ; Hou, Jianhui ; Janssen, René A.J. ; Geng, Yanhou. / Carboxylate-substituted polythiophenes for efficient fullerene-free polymer solar cells : the effect of chlorination on their properties. In: Macromolecules. 2019 ; Vol. 52, Nr. 12. blz. 4464-4474
@article{a00d1a1394ee4b2d8b76acb0382543d1,
title = "Carboxylate-substituted polythiophenes for efficient fullerene-free polymer solar cells: the effect of chlorination on their properties",
abstract = "Two new wide-bandgap polythiophenes, i.e., poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3-chloro-2,2′-bithiophene] (PDCBT-Cl) and poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3,3′-dichloro-2,2′-bithiophene] (PDCBT-2Cl) comprising 3-chloro-2,2′-bithiophene and 3,3′-dichloro-2,2′-bithiophene moieties, respectively, were synthesized for fullerene-free polymer solar cells (PSCs). For comparison, three other polymers based on [2,2′-bithiophene]-4,4′-dicarboxylate (DCBT), i.e., PDCBT, PDCBT-F, and PDCBT-2F with 2,2′-bithiophene, 3-fluoro-2,2′-bithiophene, and 3,3′-difluoro-2,2′-bithiophene as comonomers, respectively, were also prepared. PSC devices were fabricated with these polymers as donor materials and ITIC-Th1 as acceptor. The incorporation of chlorine (Cl) or fluorine (F) atoms into polymers both efficiently downshifted the highest occupied molecular orbital (HOMO) energy levels, leading to higher open-circuit voltage (Voc) in the PSCs. Owing to the proper phase-separated morphology with favorable molecular packing and miscibility, the device based on PDCBT-Cl:ITIC-Th1 exhibited efficient exciton dissociation and charge collection as well as weak charge recombination and thereby displayed the best power conversion efficiency (PCE) up to 12.38{\%}. The devices based on other polymers showed inferior PCEs (8.14{\%} for PDCBT, 10.85{\%} for PDCBT-F, 8.48{\%} for PDCBT-2F, and 6.94{\%} for PDCBT-2Cl). The monomers that are used to make PDCBT-Cl can be synthesized in relatively large scale from commercial available chemicals. All these indicate that PDCBT-Cl is a promising donor material for the large area fabrication of high-performance fullerene-free PSCs.",
author = "Qi Wang and Miaomiao Li and Xiaowei Zhang and Yunpeng Qin and Junke Wang and Jidong Zhang and Jianhui Hou and Janssen, {Ren{\'e} A.J.} and Yanhou Geng",
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doi = "10.1021/acs.macromol.9b00793",
language = "English",
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pages = "4464--4474",
journal = "Macromolecules",
issn = "0024-9297",
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Carboxylate-substituted polythiophenes for efficient fullerene-free polymer solar cells : the effect of chlorination on their properties. / Wang, Qi; Li, Miaomiao (Corresponding author); Zhang, Xiaowei; Qin, Yunpeng; Wang, Junke; Zhang, Jidong; Hou, Jianhui; Janssen, René A.J.; Geng, Yanhou (Corresponding author).

In: Macromolecules, Vol. 52, Nr. 12, 25.06.2019, blz. 4464-4474.

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

TY - JOUR

T1 - Carboxylate-substituted polythiophenes for efficient fullerene-free polymer solar cells

T2 - Macromolecules

AU - Wang,Qi

AU - Li,Miaomiao

AU - Zhang,Xiaowei

AU - Qin,Yunpeng

AU - Wang,Junke

AU - Zhang,Jidong

AU - Hou,Jianhui

AU - Janssen,René A.J.

AU - Geng,Yanhou

PY - 2019/6/25

Y1 - 2019/6/25

N2 - Two new wide-bandgap polythiophenes, i.e., poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3-chloro-2,2′-bithiophene] (PDCBT-Cl) and poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3,3′-dichloro-2,2′-bithiophene] (PDCBT-2Cl) comprising 3-chloro-2,2′-bithiophene and 3,3′-dichloro-2,2′-bithiophene moieties, respectively, were synthesized for fullerene-free polymer solar cells (PSCs). For comparison, three other polymers based on [2,2′-bithiophene]-4,4′-dicarboxylate (DCBT), i.e., PDCBT, PDCBT-F, and PDCBT-2F with 2,2′-bithiophene, 3-fluoro-2,2′-bithiophene, and 3,3′-difluoro-2,2′-bithiophene as comonomers, respectively, were also prepared. PSC devices were fabricated with these polymers as donor materials and ITIC-Th1 as acceptor. The incorporation of chlorine (Cl) or fluorine (F) atoms into polymers both efficiently downshifted the highest occupied molecular orbital (HOMO) energy levels, leading to higher open-circuit voltage (Voc) in the PSCs. Owing to the proper phase-separated morphology with favorable molecular packing and miscibility, the device based on PDCBT-Cl:ITIC-Th1 exhibited efficient exciton dissociation and charge collection as well as weak charge recombination and thereby displayed the best power conversion efficiency (PCE) up to 12.38%. The devices based on other polymers showed inferior PCEs (8.14% for PDCBT, 10.85% for PDCBT-F, 8.48% for PDCBT-2F, and 6.94% for PDCBT-2Cl). The monomers that are used to make PDCBT-Cl can be synthesized in relatively large scale from commercial available chemicals. All these indicate that PDCBT-Cl is a promising donor material for the large area fabrication of high-performance fullerene-free PSCs.

AB - Two new wide-bandgap polythiophenes, i.e., poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3-chloro-2,2′-bithiophene] (PDCBT-Cl) and poly[5,5′-bis(2-hexyldecyl)-(2,2′-bithiophene)-4,4′-dicarboxylate-alt-5,5′-3,3′-dichloro-2,2′-bithiophene] (PDCBT-2Cl) comprising 3-chloro-2,2′-bithiophene and 3,3′-dichloro-2,2′-bithiophene moieties, respectively, were synthesized for fullerene-free polymer solar cells (PSCs). For comparison, three other polymers based on [2,2′-bithiophene]-4,4′-dicarboxylate (DCBT), i.e., PDCBT, PDCBT-F, and PDCBT-2F with 2,2′-bithiophene, 3-fluoro-2,2′-bithiophene, and 3,3′-difluoro-2,2′-bithiophene as comonomers, respectively, were also prepared. PSC devices were fabricated with these polymers as donor materials and ITIC-Th1 as acceptor. The incorporation of chlorine (Cl) or fluorine (F) atoms into polymers both efficiently downshifted the highest occupied molecular orbital (HOMO) energy levels, leading to higher open-circuit voltage (Voc) in the PSCs. Owing to the proper phase-separated morphology with favorable molecular packing and miscibility, the device based on PDCBT-Cl:ITIC-Th1 exhibited efficient exciton dissociation and charge collection as well as weak charge recombination and thereby displayed the best power conversion efficiency (PCE) up to 12.38%. The devices based on other polymers showed inferior PCEs (8.14% for PDCBT, 10.85% for PDCBT-F, 8.48% for PDCBT-2F, and 6.94% for PDCBT-2Cl). The monomers that are used to make PDCBT-Cl can be synthesized in relatively large scale from commercial available chemicals. All these indicate that PDCBT-Cl is a promising donor material for the large area fabrication of high-performance fullerene-free PSCs.

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DO - 10.1021/acs.macromol.9b00793

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JF - Macromolecules

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