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

Do, Thu Trang and Rundel, Kira and Gu, Qinying and Gann, Eliot and Manzhos, Sergei and Feron, Krishna and Bell, John and McNeill, Christopher R and Sonar, Prashant (2017) 9-Fluorenone and 9,10-anthraquinone potential fused aromatic building blocks to synthesize electron acceptors for organic solar cells. New Journal of Chemistry, 41 (8). pp. 2899-2909. ISSN 1144-0546


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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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Files associated with this item cannot be displayed due to copyright restrictions.
Faculty/School / Institute/Centre: No Faculty
Faculty/School / Institute/Centre: No Faculty
Date Deposited: 28 Sep 2020 00:31
Last Modified: 02 Nov 2020 01:36
Uncontrolled Keywords: non-fullerene acceptors; low-band-gap; open-circuit voltage; photovoltaic properties; small molecules; charge-transport; perylene-diimide; polymer; diketopyrrolopyrrole; donor
Fields of Research (2008): 03 Chemical Sciences > 0399 Other Chemical Sciences > 039999 Chemical Sciences not elsewhere classified
Fields of Research (2020): 34 CHEMICAL SCIENCES > 3499 Other chemical sciences > 349999 Other chemical sciences not elsewhere classified
Identification Number or DOI: https://doi.org/10.1039/c6nj03938c
URI: http://eprints.usq.edu.au/id/eprint/39361

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