Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics

Yen Ju Cheng, Jhong Sian Wu, Ping I. Shih, Chih Yu Chang, Pei Chi Jwo, Wei Shun Kao, Chain Shu Hsu

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

By utilizing Friedel-Crafts cyclization, we have successfully designed and synthesized a ladder-type heptacyclic carbazole-dicyclopentathiophene (CDCT-C8) unit in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core. The nitrogen-directing effect of the carbazole unit facilitates the intramolecular cyclization and thereby suppresses the acid-induced dehydration, allowing us to incorporate two octyl side chains on the cyclopentadiene rings in good chemical yield. The distannyl-CDCT-C8 building block was copolymerized with benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), dithienyldiketopyrrolopyrrole (DTDPP) and quinoxaline (QX) units by Stille polymerization to afford four alternating donor-acceptor copolymers, PCDCTBT-C8, PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8, respectively. The device based on the PCDCTBT-C8:PC71BM (1:3 in wt%) blend exhibited a V oc of 0.74 V, a Jsc of 10.3 mA/cm2, a FF of 60%, delivering an impressive PCE of 4.6%. This value represents one of the best performances among carbazole-based conjugated polymers in the literatures. The corresponding PCDCTBT-C8:PC71BM blend showed a high hole mobility of 1.2 ×10-3 cm2 V-1 s-1, which is in good agreement with its high current density and fill factor. This improved performance is associated with the modification of the aliphatic side chains on the CDCT structure to optimize the interchain interactions for enhanced charge transporting. The devices based on PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8 polymers also displayed promising efficiencies of 3.5%, 2.4%, and 1.8%, respectively.

Original languageEnglish
Pages (from-to)2361-2369
Number of pages9
JournalChemistry of Materials
Volume23
Issue number9
DOIs
Publication statusPublished - May 10 2011
Externally publishedYes

Fingerprint

Cyclization
Ladders
Hole mobility
Conjugated polymers
Thiophene
Dehydration
Current density
Copolymers
Polymerization
Nitrogen
Cyclopentanes
Thiophenes
Quinoxalines
Acids
Polymers
carbazole

Keywords

  • carbazole
  • Friedel-Crafts cyclization
  • ladder-type
  • organic photovoltaics
  • polymerization

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics. / Cheng, Yen Ju; Wu, Jhong Sian; Shih, Ping I.; Chang, Chih Yu; Jwo, Pei Chi; Kao, Wei Shun; Hsu, Chain Shu.

In: Chemistry of Materials, Vol. 23, No. 9, 10.05.2011, p. 2361-2369.

Research output: Contribution to journalArticle

Cheng, Yen Ju ; Wu, Jhong Sian ; Shih, Ping I. ; Chang, Chih Yu ; Jwo, Pei Chi ; Kao, Wei Shun ; Hsu, Chain Shu. / Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics. In: Chemistry of Materials. 2011 ; Vol. 23, No. 9. pp. 2361-2369.
@article{25cd481f26ed46e0bb5d84ad4ba620a3,
title = "Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics",
abstract = "By utilizing Friedel-Crafts cyclization, we have successfully designed and synthesized a ladder-type heptacyclic carbazole-dicyclopentathiophene (CDCT-C8) unit in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core. The nitrogen-directing effect of the carbazole unit facilitates the intramolecular cyclization and thereby suppresses the acid-induced dehydration, allowing us to incorporate two octyl side chains on the cyclopentadiene rings in good chemical yield. The distannyl-CDCT-C8 building block was copolymerized with benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), dithienyldiketopyrrolopyrrole (DTDPP) and quinoxaline (QX) units by Stille polymerization to afford four alternating donor-acceptor copolymers, PCDCTBT-C8, PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8, respectively. The device based on the PCDCTBT-C8:PC71BM (1:3 in wt{\%}) blend exhibited a V oc of 0.74 V, a Jsc of 10.3 mA/cm2, a FF of 60{\%}, delivering an impressive PCE of 4.6{\%}. This value represents one of the best performances among carbazole-based conjugated polymers in the literatures. The corresponding PCDCTBT-C8:PC71BM blend showed a high hole mobility of 1.2 ×10-3 cm2 V-1 s-1, which is in good agreement with its high current density and fill factor. This improved performance is associated with the modification of the aliphatic side chains on the CDCT structure to optimize the interchain interactions for enhanced charge transporting. The devices based on PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8 polymers also displayed promising efficiencies of 3.5{\%}, 2.4{\%}, and 1.8{\%}, respectively.",
keywords = "carbazole, Friedel-Crafts cyclization, ladder-type, organic photovoltaics, polymerization",
author = "Cheng, {Yen Ju} and Wu, {Jhong Sian} and Shih, {Ping I.} and Chang, {Chih Yu} and Jwo, {Pei Chi} and Kao, {Wei Shun} and Hsu, {Chain Shu}",
year = "2011",
month = "5",
day = "10",
doi = "10.1021/cm200041v",
language = "English",
volume = "23",
pages = "2361--2369",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "9",

}

TY - JOUR

T1 - Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics

AU - Cheng, Yen Ju

AU - Wu, Jhong Sian

AU - Shih, Ping I.

AU - Chang, Chih Yu

AU - Jwo, Pei Chi

AU - Kao, Wei Shun

AU - Hsu, Chain Shu

PY - 2011/5/10

Y1 - 2011/5/10

N2 - By utilizing Friedel-Crafts cyclization, we have successfully designed and synthesized a ladder-type heptacyclic carbazole-dicyclopentathiophene (CDCT-C8) unit in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core. The nitrogen-directing effect of the carbazole unit facilitates the intramolecular cyclization and thereby suppresses the acid-induced dehydration, allowing us to incorporate two octyl side chains on the cyclopentadiene rings in good chemical yield. The distannyl-CDCT-C8 building block was copolymerized with benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), dithienyldiketopyrrolopyrrole (DTDPP) and quinoxaline (QX) units by Stille polymerization to afford four alternating donor-acceptor copolymers, PCDCTBT-C8, PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8, respectively. The device based on the PCDCTBT-C8:PC71BM (1:3 in wt%) blend exhibited a V oc of 0.74 V, a Jsc of 10.3 mA/cm2, a FF of 60%, delivering an impressive PCE of 4.6%. This value represents one of the best performances among carbazole-based conjugated polymers in the literatures. The corresponding PCDCTBT-C8:PC71BM blend showed a high hole mobility of 1.2 ×10-3 cm2 V-1 s-1, which is in good agreement with its high current density and fill factor. This improved performance is associated with the modification of the aliphatic side chains on the CDCT structure to optimize the interchain interactions for enhanced charge transporting. The devices based on PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8 polymers also displayed promising efficiencies of 3.5%, 2.4%, and 1.8%, respectively.

AB - By utilizing Friedel-Crafts cyclization, we have successfully designed and synthesized a ladder-type heptacyclic carbazole-dicyclopentathiophene (CDCT-C8) unit in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core. The nitrogen-directing effect of the carbazole unit facilitates the intramolecular cyclization and thereby suppresses the acid-induced dehydration, allowing us to incorporate two octyl side chains on the cyclopentadiene rings in good chemical yield. The distannyl-CDCT-C8 building block was copolymerized with benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), dithienyldiketopyrrolopyrrole (DTDPP) and quinoxaline (QX) units by Stille polymerization to afford four alternating donor-acceptor copolymers, PCDCTBT-C8, PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8, respectively. The device based on the PCDCTBT-C8:PC71BM (1:3 in wt%) blend exhibited a V oc of 0.74 V, a Jsc of 10.3 mA/cm2, a FF of 60%, delivering an impressive PCE of 4.6%. This value represents one of the best performances among carbazole-based conjugated polymers in the literatures. The corresponding PCDCTBT-C8:PC71BM blend showed a high hole mobility of 1.2 ×10-3 cm2 V-1 s-1, which is in good agreement with its high current density and fill factor. This improved performance is associated with the modification of the aliphatic side chains on the CDCT structure to optimize the interchain interactions for enhanced charge transporting. The devices based on PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8 polymers also displayed promising efficiencies of 3.5%, 2.4%, and 1.8%, respectively.

KW - carbazole

KW - Friedel-Crafts cyclization

KW - ladder-type

KW - organic photovoltaics

KW - polymerization

UR - http://www.scopus.com/inward/record.url?scp=79955665216&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955665216&partnerID=8YFLogxK

U2 - 10.1021/cm200041v

DO - 10.1021/cm200041v

M3 - Article

VL - 23

SP - 2361

EP - 2369

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 9

ER -