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Designing indenothiophene-based acceptor materials with efficient photovoltaic parameters for fullerene-free organic solar cells

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Abstract

Non-fullerene small molecular acceptors (NFSMAs) exhibit promising photovoltaic performance which promoted the rapid progress of organic solar cells (OSCs). In this study, an attempt is done to explore indenothiophene-based high-performance small molecular electron acceptors for organic solar cells. We have designed five acceptor molecules (M1–M5) with strong donor moiety indenothiophene linked to five different end-capped group acceptor moieties: diflouro-2-methylene-3-oxo-2,3-dihydroindene-1-ylidene)malononitrile (A1), 1-(dicyanomethylene)-2-methylene-3-oxo-2,3-dihydro-1H-indene-5,6-dicarbonitrile (A2), methyl-6-cyano-3-(dicyanomethylene)-2-methylene-1-oxo-2,3-dihydro-1H-indene-5-carboylate (A3), 2-(6-cyano-5-fluoro-2-methylene-3-oxo-2,3 dihydro-1H-indene-1-ylidene)malononitrile (A4), and (Z)-methyl 3-(benzo [c][1,2,5]thiadiazol-4-yl)-2-cyanoacrylate (A5) respectively. The structure–property relationship was studied and effects of structural modification on the optoelectronic properties of these acceptors (M1–M5) were determined systematically by comparing it with reference molecule R, which is recently reported as excellent non-fullerene-based small acceptor molecule. Among all designed molecules, M5 is proven as a suitable candidate for organic solar cell applications due to better photovoltaic properties including narrow HOMO-LUMO energy gap (2.11 eV), smallest electron mobility (λe = 0.0038 eV), highest λmax values (702.82 nm in gas) and (663.09 nm in chloroform solvent) and highest open-circuit voltage (Voc = 1.49 V) with respect to HOMOPTB7-Th–LUMOacceptor. Our results indicate that introducing more end-capped electron-accepting units is a simple and effective alternative strategy for the design of promising NFSMAs. This theoretical framework also proves that the conceptualized NFSMAs are superior and thus are recommended for the future construction of high-performance organic solar cell devices.

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Authors and Affiliations

  1. Department of Chemistry, University of Okara, Okara, 56300, Pakistan

    Zainab Afzal, Riaz Hussain, Muhammad Usman Khan, Muhammad Usman Alvi & Muhammad Yasir Mehboob

  2. Department of Applied Chemistry, Government College University, Faisalabad, 38000, Pakistan

    Muhammad Usman Khan

  3. Department of Chemistry, Khwaja Fareed University of Engineering & Information Technology, Rahim Yar Khan, 64200, Pakistan

    Muhammad Khalid, Munawar Hussain & Chaudhary Jahrukh Tariq

  4. Department of Chemistry, University of Agriculture, Faisalabad, 38000, Pakistan

    Javed Iqbal

  5. Punjab Bio-energy Institute, University of Agriculture, Faisalabad, 38040, Pakistan

    Javed Iqbal

  6. College of Natural Sciences, Department of Chemistry, Chosun University, Gwangju, 501-759, Republic of Korea

    Muhammad Adnan

  7. Renacon Pharma (PVT) Limited, Lahore, 54600, Pakistan

    Mahmood Ahmed

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  1. Zainab Afzal
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  2. Riaz Hussain
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  3. Muhammad Usman Khan
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  4. Muhammad Khalid
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Highlights

• The detailed DFT and TDDFT calculations have been performed on novel indenothiophene-based high-performance NFSMAs.

• Five acceptor molecules (M1–M5) with strong donor moiety indenothiophene linked to five different end-capped group acceptor moieties based on newly synthesized AIDIC molecule were designed and studied.

• The electronic, optical, and photovoltaic properties were studied.

• The studied compounds are proposed to be better entrants for OSC applications.

• This work may provide useful means in designing of new photovoltaic compounds.

Electronic supplementary material

ESM 1

Optimized Cartesian coordinates of our studied compounds are available in the Supporting Information file. (DOCX 213 kb).

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Afzal, Z., Hussain, R., Khan, M.U. et al. Designing indenothiophene-based acceptor materials with efficient photovoltaic parameters for fullerene-free organic solar cells. J Mol Model 26, 137 (2020). https://doi.org/10.1007/s00894-020-04386-5

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