Molecular designing of four high performance pyrazine-based non-fullerene acceptor materials with naphthalene diimide-based small organic solar cells

  • Usman AliEmail author
  • Ayesha Javed
  • Aqsa Tallat
  • Javed IqbalEmail author
  • Ali Raza
Original Paper


We design four high performance non-fullerene acceptor materials by applying strong electron withdrawing groups at the end of A-D-A-D-A type organic solar cells molecules and compute their different opto-electronic and photovoltaic properties, including absorption spectrum, electron density, solubility strength, charge mobilities for electrons and holes, stability of HOMO/LUMO energy orbitals, excitation energies required for charge transfer mechanisms, and morphology of device with the help of DFT approaches using the principles of quantum mechanics. The newly designed molecules showed strong absorption bands between 420 to 650 nm, low HOMO energy values from −7.24 to −7.28 eV, large % ETC from 35 to 65%, and small excitation energies from 2.28 to 2.47 eV in the organic solvent chloroform; 410 to 620 nm, 31 to 64%, and 2.42 to 2.56 eV, respectively, in gas phase conditions. Solubility strengths of the newly designed molecules were also high, varying from 5.3039 to 18.4749 Debye in the ground and excited states. Power conversion efficiencies of the designed molecules are expected to be high because they show better results than the R molecule. Open circuit voltages of designed molecules range from 3.67 to 3.54 V with respect to the PCBM. Reorganization energies for electron transport vary from 0.0153 to 0.0175 eV and for hole transport from 0.0231 to 0.0254 eV. This computational study proves that the newly designed molecules with non-fullerene acceptors are superior and thus are recommended for the future construction of high performance organic solar cells devices.

Graphical Abstract

Orbital’s energy comparisons of four newly designed non-fullerene acceptor materials with naphthalene diimide-based small organic solar cells


Non-fullerene acceptors Naphthalene diimide Absorption bands Frontier molecular orbitals. 



This research work was supported by the Swedish National Infrastructure for computing (SNIC) Umeå University, 901 87, Umeå, Sweden. The authors also acknowledge the technical and financial support provided by the Punjab Bio-Energy Institute and University of Agriculture, Faisalabad, Pakistan.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

894_2019_3932_MOESM1_ESM.docx (1.3 mb)
ESM 1 (DOCX 1368 kb)


  1. 1.
    Chamberlain G (1983) Organic solar cells: a review. Solar cells 8(1):47–83CrossRefGoogle Scholar
  2. 2.
    Paish O (2002) Small hydro power: technology and current status. Renew Sust Energ Rev 6(6):537–556CrossRefGoogle Scholar
  3. 3.
    Burton T et al (2011) Wind energy handbook. Wiley, ChichesterCrossRefGoogle Scholar
  4. 4.
    Whicker FW, Schultz V (1982) Radioecology: nuclear energy and the environment, vol. 2. CRC, Boca RatonGoogle Scholar
  5. 5.
    Pillai S et al (2007) Surface plasmon enhanced silicon solar cells. J Appl Phys 101(9):093105CrossRefGoogle Scholar
  6. 6.
    Kline SJ, Rosenberg N (2010) An overview of innovation. Studies on science and the innovation process: selected works of Nathan Rosenberg. World Scientific, Singapore, pp 173–203Google Scholar
  7. 7.
    Scharber MC et al (2006) Design rules for donors in bulk-heterojunction solar cells—towards 10% energy-conversion efficiency. Adv Mater 18(6):789–794CrossRefGoogle Scholar
  8. 8.
    Scharber MC, Sariciftci NS (2013) Efficiency of bulk-heterojunction organic solar cells. Prog Polym Sci 38(12):1929–1940PubMedPubMedCentralCrossRefGoogle Scholar
  9. 9.
    Meng D et al (2015) High-performance solution-processed non-fullerene organic solar cells based on selenophene-containing perylene bisimide acceptor. J Am Chem Soc 138(1):375–380PubMedCrossRefGoogle Scholar
  10. 10.
    Baran D et al (2017) Reducing the efficiency–stability–cost gap of organic photovoltaics with highly efficient and stable small molecule acceptor ternary solar cells. Nat Mater 16(3):363PubMedCrossRefGoogle Scholar
  11. 11.
    Zhou J et al (2013) Solution-processed and high-performance organic solar cells using small molecules with a benzodithiophene unit. J Am Chem Soc 135(23):8484–8487PubMedCrossRefGoogle Scholar
  12. 12.
    Zhou J et al (2012) Small molecules based on benzo [1, 2-b: 4, 5-b′] dithiophene unit for high-performance solution-processed organic solar cells. J Am Chem Soc 134(39):16345–16351PubMedCrossRefGoogle Scholar
  13. 13.
    Ala'a FE et al (2014) Recent advances of non-fullerene, small molecular acceptors for solution processed bulk heterojunction solar cells. J Mater Chem A 2(5):1201–1213CrossRefGoogle Scholar
  14. 14.
    Günes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107(4):1324–1338PubMedCrossRefGoogle Scholar
  15. 15.
    Zhang Y et al (2015) Fluorene-centered perylene monoimides as potential non-fullerene acceptor in organic solar cells. Org Electron 21:184–191CrossRefGoogle Scholar
  16. 16.
    Kwon OK et al (2015) An all-small-molecule organic solar cell with high efficiency nonfullerene acceptor. Adv Mater 27(11):1951–1956PubMedCrossRefGoogle Scholar
  17. 17.
    Spitler EL, McClintock SP, Haley MM (2007) Dynamic proton-induced emission switching in donor-functionalized dehydrobenzopyrid [15] annulenes. J Org Chem 72(18):6692–6699PubMedCrossRefGoogle Scholar
  18. 18.
    Brédas J-L et al (2002) Organic semiconductors: a theoretical characterization of the basic parameters governing charge transport. Proc Natl Acad Sci 99(9):5804–5809PubMedCrossRefGoogle Scholar
  19. 19.
    Zhou H et al (2010) Enhanced photovoltaic performance of low-bandgap polymers with deep LUMO levels. Angew Chem 122(43):8164–8167CrossRefGoogle Scholar
  20. 20.
    Thomas CM, Darensbourg MY, Hall MB (2007) Computational definition of a mixed valent Fe (II) Fe (I) model of the [FeFe] hydrogenase active site resting state. J Inorg Biochem 101(11–12):1752–1757PubMedCrossRefGoogle Scholar
  21. 21.
    Mihailetchi VD et al (2006) Charge transport and photocurrent generation in poly (3-hexylthiophene): methanofullerene bulk-heterojunction solar cells. Adv Funct Mater 16(5):699–708CrossRefGoogle Scholar
  22. 22.
    Bach U et al (1998) Solid-state dye-sensitized mesoporous TiO 2 solar cells with high photon-to-electron conversion efficiencies. Nature 395(6702):583CrossRefGoogle Scholar
  23. 23.
    Hagberg DP et al (2007) Tuning the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells. J Org Chem 72(25):9550–9556PubMedCrossRefGoogle Scholar
  24. 24.
    Tamayo AB, Walker B, Nguyen T-Q (2008) A low band gap, solution processable oligothiophene with a diketopyrrolopyrrole core for use in organic solar cells. J Phys Chem C 112(30):11545–11551CrossRefGoogle Scholar
  25. 25.
    O'regan B, Grätzel M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 353(6346):737CrossRefGoogle Scholar
  26. 26.
    Park SH et al (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100%. Nat Photonics 3(5):297CrossRefGoogle Scholar
  27. 27.
    Spanhel L, Anderson MA (1991) Semiconductor clusters in the sol-gel process: quantized aggregation, gelation, and crystal growth in concentrated zinc oxide colloids. J Am Chem Soc 113(8):2826–2833CrossRefGoogle Scholar
  28. 28.
    Sung MJ et al (2017) Naphthalene diimide-based small molecule acceptors for fullerene-free organic solar cells. Sol Energy 150:90–95CrossRefGoogle Scholar
  29. 29.
    Manzoor F et al (2018) Theoretical calculations of the optical and electronic properties of dithienosilole-and dithiophene-based donor materials for organic solar cells. ChemistrySelect 3(5):1593–1601Google Scholar
  30. 30.
    Irfan M et al (2018) Tuning the optoelectronic properties of Naphtho-Dithiophene-based A-D-A type small donor molecules for bulk hetero-junction organic solar cells. ChemistrySelect 3(8):2352–2358Google Scholar
  31. 31.
    He Z et al (2011) Simultaneous enhancement of open-circuit voltage, short-circuit current density, and fill factor in polymer solar cells. Adv Mater 23(40):4636–4643PubMedCrossRefGoogle Scholar
  32. 32.
    Bai H et al (2014) Acceptor–donor–acceptor small molecules based on indacenodithiophene for efficient organic solar cells. ACS Appl Mater Interfaces 6(11):8426–8433PubMedCrossRefGoogle Scholar
  33. 33.
    Rand BP, Burk DP, Forrest SR (2007) Offset energies at organic semiconductor heterojunctions and their influence on the open-circuit voltage of thin-film solar cells. Phys Rev B 75(11):115327CrossRefGoogle Scholar
  34. 34.
    Brédas J-L et al (2009) Molecular understanding of organic solar cells: the challenges. Acc Chem Res 42(11):1691–1699PubMedCrossRefGoogle Scholar
  35. 35.
    Bisquert J et al (2004) Determination of rate constants for charge transfer and the distribution of semiconductor and electrolyte electronic energy levels in dye-sensitized solar cells by open-circuit photovoltage decay method. J Am Chem Soc 126(41):13550–13559PubMedCrossRefGoogle Scholar
  36. 36.
    Tang S, Zhang J (2012) Design of donors with broad absorption regions and suitable frontier molecular orbitals to match typical acceptors via substitution on oligo (thienylenevinylene) toward solar cells. J Comput Chem 33(15):1353–1363PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of AgricultureFaisalabadPakistan
  2. 2.Punjab Bio-energy InstituteUniversity of AgricultureFaisalabadPakistan
  3. 3.Department of PhysicsUniversity of AgricultureFaisalabadPakistan

Personalised recommendations