9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells

Thu Trang Do, Kira Rundel, Qinying Gu, Eliot Gann, Sergei Manzhos, Krishna Feron, John Bell, Christopher R. McNeill, Prashant Sonar

Research output: Contribution to journalArticleResearchpeer-review

Abstract

In this work, for the first time we used two novel fused aromatic conjugated electron withdrawing moieties 9-fluorenone and 9,10-anthraquinone, respectively, to design two non-fullerene acceptors and evaluated their viability in solution-processable organic solar cells (OSCs). 9-Fluorenone and 9,10-anthraquinone were used as core electron withdrawing blocks in combination with another common strong electron accepting diketopyrrolopyrrole (DPP) end-capping group. The compounds 6,6′-(5,5′-(9-oxo-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-FN-DPP) and 6,6′-(5,5′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-ANQ-DPP) were synthesized via a Suzuki coupling reaction and characterized completely. The new acceptors exhibit good solubility in common organic solvents and good thermal stability with 5% weight loss above 360 °C. DPP-FN-DPP and DPP-ANQ-DPP possess a broad absorption band at 300-700 nm with optical band-gaps of 1.75 and 1.71 eV, respectively. The use of different core acceptor building blocks resulted in a difference in LUMO and HOMO energy levels. Inverted OSC devices employing P3HT as the donor polymer and DPP-FN-DPP and DPP-ANQ-DPP as acceptors yielded quite high open-circuit voltages (VOC) of 0.85-0.98 V, benefiting from the relatively low-lying LUMO energy levels of the two acceptors. Among both, OSC devices based on DPP-FN-DPP as acceptor exhibits the highest performance with a VOC of 0.97 V, a short-circuit current density (JSC) of 3.2 mA cm-2, a fill factor (FF) of 37%, and an overall power conversion efficiency of 1.2%.

Original languageEnglish
Pages (from-to)2899-2909
Number of pages11
JournalNew Journal of Chemistry
Volume41
Issue number8
DOIs
Publication statusPublished - 2017

Cite this

Do, Thu Trang ; Rundel, Kira ; Gu, Qinying ; Gann, Eliot ; Manzhos, Sergei ; Feron, Krishna ; Bell, John ; McNeill, Christopher R. ; Sonar, Prashant. / 9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells. In: New Journal of Chemistry. 2017 ; Vol. 41, No. 8. pp. 2899-2909.
@article{46b90b031a784a66b2bc3e4dbba94789,
title = "9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells",
abstract = "In this work, for the first time we used two novel fused aromatic conjugated electron withdrawing moieties 9-fluorenone and 9,10-anthraquinone, respectively, to design two non-fullerene acceptors and evaluated their viability in solution-processable organic solar cells (OSCs). 9-Fluorenone and 9,10-anthraquinone were used as core electron withdrawing blocks in combination with another common strong electron accepting diketopyrrolopyrrole (DPP) end-capping group. The compounds 6,6′-(5,5′-(9-oxo-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-FN-DPP) and 6,6′-(5,5′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-ANQ-DPP) were synthesized via a Suzuki coupling reaction and characterized completely. The new acceptors exhibit good solubility in common organic solvents and good thermal stability with 5{\%} weight loss above 360 °C. DPP-FN-DPP and DPP-ANQ-DPP possess a broad absorption band at 300-700 nm with optical band-gaps of 1.75 and 1.71 eV, respectively. The use of different core acceptor building blocks resulted in a difference in LUMO and HOMO energy levels. Inverted OSC devices employing P3HT as the donor polymer and DPP-FN-DPP and DPP-ANQ-DPP as acceptors yielded quite high open-circuit voltages (VOC) of 0.85-0.98 V, benefiting from the relatively low-lying LUMO energy levels of the two acceptors. Among both, OSC devices based on DPP-FN-DPP as acceptor exhibits the highest performance with a VOC of 0.97 V, a short-circuit current density (JSC) of 3.2 mA cm-2, a fill factor (FF) of 37{\%}, and an overall power conversion efficiency of 1.2{\%}.",
author = "Do, {Thu Trang} and Kira Rundel and Qinying Gu and Eliot Gann and Sergei Manzhos and Krishna Feron and John Bell and McNeill, {Christopher R.} and Prashant Sonar",
year = "2017",
doi = "10.1039/c6nj03938c",
language = "English",
volume = "41",
pages = "2899--2909",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "The Royal Society of Chemistry",
number = "8",

}

9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells. / Do, Thu Trang; Rundel, Kira; Gu, Qinying; Gann, Eliot; Manzhos, Sergei; Feron, Krishna; Bell, John; McNeill, Christopher R.; Sonar, Prashant.

In: New Journal of Chemistry, Vol. 41, No. 8, 2017, p. 2899-2909.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - 9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells

AU - Do, Thu Trang

AU - Rundel, Kira

AU - Gu, Qinying

AU - Gann, Eliot

AU - Manzhos, Sergei

AU - Feron, Krishna

AU - Bell, John

AU - McNeill, Christopher R.

AU - Sonar, Prashant

PY - 2017

Y1 - 2017

N2 - In this work, for the first time we used two novel fused aromatic conjugated electron withdrawing moieties 9-fluorenone and 9,10-anthraquinone, respectively, to design two non-fullerene acceptors and evaluated their viability in solution-processable organic solar cells (OSCs). 9-Fluorenone and 9,10-anthraquinone were used as core electron withdrawing blocks in combination with another common strong electron accepting diketopyrrolopyrrole (DPP) end-capping group. The compounds 6,6′-(5,5′-(9-oxo-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-FN-DPP) and 6,6′-(5,5′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-ANQ-DPP) were synthesized via a Suzuki coupling reaction and characterized completely. The new acceptors exhibit good solubility in common organic solvents and good thermal stability with 5% weight loss above 360 °C. DPP-FN-DPP and DPP-ANQ-DPP possess a broad absorption band at 300-700 nm with optical band-gaps of 1.75 and 1.71 eV, respectively. The use of different core acceptor building blocks resulted in a difference in LUMO and HOMO energy levels. Inverted OSC devices employing P3HT as the donor polymer and DPP-FN-DPP and DPP-ANQ-DPP as acceptors yielded quite high open-circuit voltages (VOC) of 0.85-0.98 V, benefiting from the relatively low-lying LUMO energy levels of the two acceptors. Among both, OSC devices based on DPP-FN-DPP as acceptor exhibits the highest performance with a VOC of 0.97 V, a short-circuit current density (JSC) of 3.2 mA cm-2, a fill factor (FF) of 37%, and an overall power conversion efficiency of 1.2%.

AB - In this work, for the first time we used two novel fused aromatic conjugated electron withdrawing moieties 9-fluorenone and 9,10-anthraquinone, respectively, to design two non-fullerene acceptors and evaluated their viability in solution-processable organic solar cells (OSCs). 9-Fluorenone and 9,10-anthraquinone were used as core electron withdrawing blocks in combination with another common strong electron accepting diketopyrrolopyrrole (DPP) end-capping group. The compounds 6,6′-(5,5′-(9-oxo-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-FN-DPP) and 6,6′-(5,5′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-butyloctyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP-ANQ-DPP) were synthesized via a Suzuki coupling reaction and characterized completely. The new acceptors exhibit good solubility in common organic solvents and good thermal stability with 5% weight loss above 360 °C. DPP-FN-DPP and DPP-ANQ-DPP possess a broad absorption band at 300-700 nm with optical band-gaps of 1.75 and 1.71 eV, respectively. The use of different core acceptor building blocks resulted in a difference in LUMO and HOMO energy levels. Inverted OSC devices employing P3HT as the donor polymer and DPP-FN-DPP and DPP-ANQ-DPP as acceptors yielded quite high open-circuit voltages (VOC) of 0.85-0.98 V, benefiting from the relatively low-lying LUMO energy levels of the two acceptors. Among both, OSC devices based on DPP-FN-DPP as acceptor exhibits the highest performance with a VOC of 0.97 V, a short-circuit current density (JSC) of 3.2 mA cm-2, a fill factor (FF) of 37%, and an overall power conversion efficiency of 1.2%.

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U2 - 10.1039/c6nj03938c

DO - 10.1039/c6nj03938c

M3 - Article

VL - 41

SP - 2899

EP - 2909

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 8

ER -