Heteroarene-fused πconjugated main-chain polymers containing 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole or 2,5-bis(4- octylthiophen-2-yl)thiazolo[5,4-d]thiazole and their application to photovoltaic devices

Tae Wan Lee, Nam Su Kang, Jae Woong Yu, Mai Ha Hoang, Kyung Hwan Kim, Jung Il Jin, Dong Hoon Choi

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30 Citations (Scopus)

Abstract

Two conjugated main-chain polymers consisting of heteroarene-fused πconjuagted donor moiety alternating with 4,7-bis(5-bromo-4-octylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (P1) or 2,5-bis(5-bromo-4-octylthiophen-2-yl) thiazolo[5,4-d]thiazole (P2) units have been synthesized. They are intrinsically amorphous in nature and do not exhibit crystalline melting temperatures during thermal analysis. The effect of the fused rings on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers has been investigated. The polymer (P1) containing 4,7-bis(5-bromo-4- octylthiophen-2-yl)benzo[c][1,2,5] thiadiazole has a broad absorption extending from 300 to 600 nm with optical bandgaps as low as 2.02 eV. The HOMO levels (5.42 to 5.29 eV) are more sensitive to the choice of acceptor. The polymers were employed to fabricate organic photovoltaic cells with methanofullerene [6,6]-phenyl C71-butyric acid methyl ester (PC71BM). As a result, the polymer solar cell device containing P1 had the best preliminary results with an open-circuit voltage of 0.61 V, a short-circuit current density of 6.19 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency of 1.21%.

Original languageEnglish
Pages (from-to)5921-5929
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume48
Issue number24
DOIs
Publication statusPublished - 2010 Dec 15

Fingerprint

Thiadiazoles
Thiazoles
Polymers
Butyric acid
Butyric Acid
Photovoltaic cells
Optical band gaps
Open circuit voltage
Short circuit currents
Thermoanalysis
Conversion efficiency
Melting point
Charge transfer
Esters
Current density
Crystalline materials

Keywords

  • bulk heterojunction
  • conjugated polymers
  • donor-acceptor
  • fluorescence
  • heteroarene-fused ring
  • photophysics
  • solar cell
  • synthesis

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

@article{330a8952f32d41bf8136ff947c31e306,
title = "Heteroarene-fused πconjugated main-chain polymers containing 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole or 2,5-bis(4- octylthiophen-2-yl)thiazolo[5,4-d]thiazole and their application to photovoltaic devices",
abstract = "Two conjugated main-chain polymers consisting of heteroarene-fused πconjuagted donor moiety alternating with 4,7-bis(5-bromo-4-octylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (P1) or 2,5-bis(5-bromo-4-octylthiophen-2-yl) thiazolo[5,4-d]thiazole (P2) units have been synthesized. They are intrinsically amorphous in nature and do not exhibit crystalline melting temperatures during thermal analysis. The effect of the fused rings on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers has been investigated. The polymer (P1) containing 4,7-bis(5-bromo-4- octylthiophen-2-yl)benzo[c][1,2,5] thiadiazole has a broad absorption extending from 300 to 600 nm with optical bandgaps as low as 2.02 eV. The HOMO levels (5.42 to 5.29 eV) are more sensitive to the choice of acceptor. The polymers were employed to fabricate organic photovoltaic cells with methanofullerene [6,6]-phenyl C71-butyric acid methyl ester (PC71BM). As a result, the polymer solar cell device containing P1 had the best preliminary results with an open-circuit voltage of 0.61 V, a short-circuit current density of 6.19 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency of 1.21{\%}.",
keywords = "bulk heterojunction, conjugated polymers, donor-acceptor, fluorescence, heteroarene-fused ring, photophysics, solar cell, synthesis",
author = "Lee, {Tae Wan} and Kang, {Nam Su} and Yu, {Jae Woong} and Hoang, {Mai Ha} and Kim, {Kyung Hwan} and Jin, {Jung Il} and Choi, {Dong Hoon}",
year = "2010",
month = "12",
day = "15",
doi = "10.1002/pola.24405",
language = "English",
volume = "48",
pages = "5921--5929",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
issn = "0887-624X",
publisher = "John Wiley and Sons Inc.",
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TY - JOUR

T1 - Heteroarene-fused πconjugated main-chain polymers containing 4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole or 2,5-bis(4- octylthiophen-2-yl)thiazolo[5,4-d]thiazole and their application to photovoltaic devices

AU - Lee, Tae Wan

AU - Kang, Nam Su

AU - Yu, Jae Woong

AU - Hoang, Mai Ha

AU - Kim, Kyung Hwan

AU - Jin, Jung Il

AU - Choi, Dong Hoon

PY - 2010/12/15

Y1 - 2010/12/15

N2 - Two conjugated main-chain polymers consisting of heteroarene-fused πconjuagted donor moiety alternating with 4,7-bis(5-bromo-4-octylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (P1) or 2,5-bis(5-bromo-4-octylthiophen-2-yl) thiazolo[5,4-d]thiazole (P2) units have been synthesized. They are intrinsically amorphous in nature and do not exhibit crystalline melting temperatures during thermal analysis. The effect of the fused rings on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers has been investigated. The polymer (P1) containing 4,7-bis(5-bromo-4- octylthiophen-2-yl)benzo[c][1,2,5] thiadiazole has a broad absorption extending from 300 to 600 nm with optical bandgaps as low as 2.02 eV. The HOMO levels (5.42 to 5.29 eV) are more sensitive to the choice of acceptor. The polymers were employed to fabricate organic photovoltaic cells with methanofullerene [6,6]-phenyl C71-butyric acid methyl ester (PC71BM). As a result, the polymer solar cell device containing P1 had the best preliminary results with an open-circuit voltage of 0.61 V, a short-circuit current density of 6.19 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency of 1.21%.

AB - Two conjugated main-chain polymers consisting of heteroarene-fused πconjuagted donor moiety alternating with 4,7-bis(5-bromo-4-octylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (P1) or 2,5-bis(5-bromo-4-octylthiophen-2-yl) thiazolo[5,4-d]thiazole (P2) units have been synthesized. They are intrinsically amorphous in nature and do not exhibit crystalline melting temperatures during thermal analysis. The effect of the fused rings on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers has been investigated. The polymer (P1) containing 4,7-bis(5-bromo-4- octylthiophen-2-yl)benzo[c][1,2,5] thiadiazole has a broad absorption extending from 300 to 600 nm with optical bandgaps as low as 2.02 eV. The HOMO levels (5.42 to 5.29 eV) are more sensitive to the choice of acceptor. The polymers were employed to fabricate organic photovoltaic cells with methanofullerene [6,6]-phenyl C71-butyric acid methyl ester (PC71BM). As a result, the polymer solar cell device containing P1 had the best preliminary results with an open-circuit voltage of 0.61 V, a short-circuit current density of 6.19 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency of 1.21%.

KW - bulk heterojunction

KW - conjugated polymers

KW - donor-acceptor

KW - fluorescence

KW - heteroarene-fused ring

KW - photophysics

KW - solar cell

KW - synthesis

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VL - 48

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JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

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