Regioisomeric Polymer Semiconductors Based on Cyano-Functionalized Dialkoxybithiophenes: Structure–Property Relationship and Photovoltaic Performance

Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar cells. However, how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood. Three regioisomeric cyano-functionali...

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Veröffentlicht in:Transactions of Tianjin University 2022-10, Vol.28 (5), p.385-397
Hauptverfasser: Bai, Qingqing, Huang, Jun, Guo, Han, Ma, Suxiang, Yang, Jie, Liu, Bin, Yang, Kun, Sun, Huiliang, Woo, Han Young, Niu, Li, Guo, Xugang
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container_issue 5
container_start_page 385
container_title Transactions of Tianjin University
container_volume 28
creator Bai, Qingqing
Huang, Jun
Guo, Han
Ma, Suxiang
Yang, Jie
Liu, Bin
Yang, Kun
Sun, Huiliang
Woo, Han Young
Niu, Li
Guo, Xugang
description Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar cells. However, how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood. Three regioisomeric cyano-functionalized dialkoxybithiophenes BT HH , BT HT , and BT TT with head-to-head, head-to-tail, and tail-to-tail linkage, respectively, were synthesized and characterized in this work. The resulting polymer semiconductors (PBDTBTs) based on these building blocks were prepared accordingly. The regiochemistry and property relationships of PBDTBTs were investigated in detail. The BT HH moiety has a higher torsional barrier than the analogs BT HT and BT TT , and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers, such as optical absorption, band gap, and energy levels of frontier molecular orbitals. Organic field-effect transistors based on PBDTBT HH had higher hole mobility (4.4 × 10 −3 cm 2 /(V·s)) than those (ca. 10 −4 cm 2 /(V·s)) of the other two polymer analogs. Significantly different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron donors. Such difference was probed in greater detail by performing space-charge-limited current mobility, thin-film morphology, and transient photocurrent/photovoltage characterizations. The findings highlight that the BT HH unit is a promising building block for the construction of polymer donors for high-performance organic photovoltaic cells. Graphical abstract
doi_str_mv 10.1007/s12209-022-00323-0
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However, how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood. Three regioisomeric cyano-functionalized dialkoxybithiophenes BT HH , BT HT , and BT TT with head-to-head, head-to-tail, and tail-to-tail linkage, respectively, were synthesized and characterized in this work. The resulting polymer semiconductors (PBDTBTs) based on these building blocks were prepared accordingly. The regiochemistry and property relationships of PBDTBTs were investigated in detail. The BT HH moiety has a higher torsional barrier than the analogs BT HT and BT TT , and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers, such as optical absorption, band gap, and energy levels of frontier molecular orbitals. Organic field-effect transistors based on PBDTBT HH had higher hole mobility (4.4 × 10 −3 cm 2 /(V·s)) than those (ca. 10 −4 cm 2 /(V·s)) of the other two polymer analogs. Significantly different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron donors. Such difference was probed in greater detail by performing space-charge-limited current mobility, thin-film morphology, and transient photocurrent/photovoltage characterizations. The findings highlight that the BT HH unit is a promising building block for the construction of polymer donors for high-performance organic photovoltaic cells. 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Tianjin Univ</addtitle><description>Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar cells. However, how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood. Three regioisomeric cyano-functionalized dialkoxybithiophenes BT HH , BT HT , and BT TT with head-to-head, head-to-tail, and tail-to-tail linkage, respectively, were synthesized and characterized in this work. The resulting polymer semiconductors (PBDTBTs) based on these building blocks were prepared accordingly. The regiochemistry and property relationships of PBDTBTs were investigated in detail. The BT HH moiety has a higher torsional barrier than the analogs BT HT and BT TT , and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers, such as optical absorption, band gap, and energy levels of frontier molecular orbitals. Organic field-effect transistors based on PBDTBT HH had higher hole mobility (4.4 × 10 −3 cm 2 /(V·s)) than those (ca. 10 −4 cm 2 /(V·s)) of the other two polymer analogs. Significantly different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron donors. Such difference was probed in greater detail by performing space-charge-limited current mobility, thin-film morphology, and transient photocurrent/photovoltage characterizations. The findings highlight that the BT HH unit is a promising building block for the construction of polymer donors for high-performance organic photovoltaic cells. 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Tianjin Univ</stitle><date>2022-10-01</date><risdate>2022</risdate><volume>28</volume><issue>5</issue><spage>385</spage><epage>397</epage><pages>385-397</pages><issn>1006-4982</issn><eissn>1995-8196</eissn><abstract>Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar cells. However, how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly understood. Three regioisomeric cyano-functionalized dialkoxybithiophenes BT HH , BT HT , and BT TT with head-to-head, head-to-tail, and tail-to-tail linkage, respectively, were synthesized and characterized in this work. The resulting polymer semiconductors (PBDTBTs) based on these building blocks were prepared accordingly. The regiochemistry and property relationships of PBDTBTs were investigated in detail. The BT HH moiety has a higher torsional barrier than the analogs BT HT and BT TT , and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers, such as optical absorption, band gap, and energy levels of frontier molecular orbitals. Organic field-effect transistors based on PBDTBT HH had higher hole mobility (4.4 × 10 −3 cm 2 /(V·s)) than those (ca. 10 −4 cm 2 /(V·s)) of the other two polymer analogs. Significantly different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron donors. Such difference was probed in greater detail by performing space-charge-limited current mobility, thin-film morphology, and transient photocurrent/photovoltage characterizations. The findings highlight that the BT HH unit is a promising building block for the construction of polymer donors for high-performance organic photovoltaic cells. 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source SpringerNature Journals; Alma/SFX Local Collection
subjects Analogs
Circuits
Energy gap
Energy levels
Engineering
Field effect transistors
Hole mobility
Humanities and Social Sciences
Mechanical Engineering
Molecular orbitals
multidisciplinary
Optical properties
Optoelectronics
Organic semiconductors
Photoelectric effect
Photovoltaic cells
Polymers
Regioselectivity
Research Article
Science
Semiconductor devices
Semiconductors
Short circuit currents
Solar cells
Thin films
title Regioisomeric Polymer Semiconductors Based on Cyano-Functionalized Dialkoxybithiophenes: Structure–Property Relationship and Photovoltaic Performance
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