Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells

Jinwoo Kim, Sung Heum Park, Shinuk Cho, Youngeup Jin, Jaehong Kim, Il Kim, Jin Sook Lee, Joo Hyun Kim, Han Young Woo, Kwanghee Lee, Hongsuk Suh

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazole (DTBT) unit by Suzuki conditions. The newly synthesized copolymers, poly(2,6-((4,4-bis(2-ethylhexyl)-4H-cyclopenta[def]phenanthrene))-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PCPP-DTBT), and poly(2,6-(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[def]phenanthrene)-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PBEHPCPP-DTBT), contain dialkyl and bis(alkoxyphenyl) groups in the CPP unit, respectively. The HOMO-LUMO energy bandgaps of these materials, estimated from UV-vis spectroscopy and cyclic voltammetry (CV), were 2.00 eV for PCPP-DTBT and 1.80 eV for PBEHPCPP-DTBT. Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-C71-butyric acid methyl ester (PC71BM) gave power conversion efficiencies as 1.00% for PCPP-DTBT and 1.12% for PBEHPCPP-DTBT under AM 1.5, 100 mW/cm2.

Original languageEnglish
Pages (from-to)390-396
Number of pages7
JournalPolymer
Volume51
Issue number2
DOIs
Publication statusPublished - 2010 Jan 21
Externally publishedYes

Fingerprint

Photovoltaic cells
Heterojunctions
Solar cells
Energy gap
Bearings (structural)
Copolymers
Derivatives
Butyric acid
Conjugated polymers
Ultraviolet spectroscopy
Conversion efficiency
Cyclic voltammetry
Esters
Polymers
phenanthrene
benzo-1,2,3-thiadiazole
Butyric Acid

Keywords

  • Benzothiadiazole
  • Cyclopentaphenanthrene
  • Polymer solar cell

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells. / Kim, Jinwoo; Park, Sung Heum; Cho, Shinuk; Jin, Youngeup; Kim, Jaehong; Kim, Il; Lee, Jin Sook; Kim, Joo Hyun; Woo, Han Young; Lee, Kwanghee; Suh, Hongsuk.

In: Polymer, Vol. 51, No. 2, 21.01.2010, p. 390-396.

Research output: Contribution to journalArticle

Kim, Jinwoo ; Park, Sung Heum ; Cho, Shinuk ; Jin, Youngeup ; Kim, Jaehong ; Kim, Il ; Lee, Jin Sook ; Kim, Joo Hyun ; Woo, Han Young ; Lee, Kwanghee ; Suh, Hongsuk. / Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells. In: Polymer. 2010 ; Vol. 51, No. 2. pp. 390-396.
@article{1fbd311f4acd4ebbbff66c665bb5b2c3,
title = "Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells",
abstract = "A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazole (DTBT) unit by Suzuki conditions. The newly synthesized copolymers, poly(2,6-((4,4-bis(2-ethylhexyl)-4H-cyclopenta[def]phenanthrene))-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PCPP-DTBT), and poly(2,6-(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[def]phenanthrene)-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PBEHPCPP-DTBT), contain dialkyl and bis(alkoxyphenyl) groups in the CPP unit, respectively. The HOMO-LUMO energy bandgaps of these materials, estimated from UV-vis spectroscopy and cyclic voltammetry (CV), were 2.00 eV for PCPP-DTBT and 1.80 eV for PBEHPCPP-DTBT. Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-C71-butyric acid methyl ester (PC71BM) gave power conversion efficiencies as 1.00{\%} for PCPP-DTBT and 1.12{\%} for PBEHPCPP-DTBT under AM 1.5, 100 mW/cm2.",
keywords = "Benzothiadiazole, Cyclopentaphenanthrene, Polymer solar cell",
author = "Jinwoo Kim and Park, {Sung Heum} and Shinuk Cho and Youngeup Jin and Jaehong Kim and Il Kim and Lee, {Jin Sook} and Kim, {Joo Hyun} and Woo, {Han Young} and Kwanghee Lee and Hongsuk Suh",
year = "2010",
month = "1",
day = "21",
doi = "10.1016/j.polymer.2009.12.009",
language = "English",
volume = "51",
pages = "390--396",
journal = "Polymer (United Kingdom)",
issn = "0032-3861",
publisher = "Elsevier BV",
number = "2",

}

TY - JOUR

T1 - Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells

AU - Kim, Jinwoo

AU - Park, Sung Heum

AU - Cho, Shinuk

AU - Jin, Youngeup

AU - Kim, Jaehong

AU - Kim, Il

AU - Lee, Jin Sook

AU - Kim, Joo Hyun

AU - Woo, Han Young

AU - Lee, Kwanghee

AU - Suh, Hongsuk

PY - 2010/1/21

Y1 - 2010/1/21

N2 - A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazole (DTBT) unit by Suzuki conditions. The newly synthesized copolymers, poly(2,6-((4,4-bis(2-ethylhexyl)-4H-cyclopenta[def]phenanthrene))-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PCPP-DTBT), and poly(2,6-(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[def]phenanthrene)-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PBEHPCPP-DTBT), contain dialkyl and bis(alkoxyphenyl) groups in the CPP unit, respectively. The HOMO-LUMO energy bandgaps of these materials, estimated from UV-vis spectroscopy and cyclic voltammetry (CV), were 2.00 eV for PCPP-DTBT and 1.80 eV for PBEHPCPP-DTBT. Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-C71-butyric acid methyl ester (PC71BM) gave power conversion efficiencies as 1.00% for PCPP-DTBT and 1.12% for PBEHPCPP-DTBT under AM 1.5, 100 mW/cm2.

AB - A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazole (DTBT) unit by Suzuki conditions. The newly synthesized copolymers, poly(2,6-((4,4-bis(2-ethylhexyl)-4H-cyclopenta[def]phenanthrene))-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PCPP-DTBT), and poly(2,6-(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[def]phenanthrene)-alt-(4,7-((2-thienyl)-2,1,3-benzothiadiazole))) (PBEHPCPP-DTBT), contain dialkyl and bis(alkoxyphenyl) groups in the CPP unit, respectively. The HOMO-LUMO energy bandgaps of these materials, estimated from UV-vis spectroscopy and cyclic voltammetry (CV), were 2.00 eV for PCPP-DTBT and 1.80 eV for PBEHPCPP-DTBT. Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-C71-butyric acid methyl ester (PC71BM) gave power conversion efficiencies as 1.00% for PCPP-DTBT and 1.12% for PBEHPCPP-DTBT under AM 1.5, 100 mW/cm2.

KW - Benzothiadiazole

KW - Cyclopentaphenanthrene

KW - Polymer solar cell

UR - http://www.scopus.com/inward/record.url?scp=73949159464&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=73949159464&partnerID=8YFLogxK

U2 - 10.1016/j.polymer.2009.12.009

DO - 10.1016/j.polymer.2009.12.009

M3 - Article

VL - 51

SP - 390

EP - 396

JO - Polymer (United Kingdom)

JF - Polymer (United Kingdom)

SN - 0032-3861

IS - 2

ER -