Skip to main content
SpringerLink
Log in

DFT-guided structural modeling of end-group acceptors at Y123 core for sensitizers as high-performance organic solar dyes and NLO responses

  • Original Paper
  • Published:
Journal of Molecular Modeling Aims and scope Submit manuscript

Abstract

Context

The organic solar cells (OSCs) are being developed with the goal of improving their photovoltaic capabilities. Here, utilizing computational methods, six new nonfullerene acceptors (NFA) comprising dyes (A1–A6) have been created by end-group alterations of the Y123 framework as a standard (R).

Methods

The DFT-based investigations at B3LYP/6-31G + (d,p) level were applied to evaluate their properties. The planar geometries associated with these structures, which lead to improved conjugation, were validated by the estimation of molecular geometries. Dyes A1–A6 have shorter Egap than R, according to a frontier molecular orbital (FMO) investigation, which encourages charge transfer in them. The dyes with their maximum absorption range were shown by optical properties to be 692–711 nm, which is significantly better than R with its 684 nm range. Their electrostatic and Mulliken charge patterns provided additional evidence of the significant separation of charges within these structures. All the dyes A1–A6 had improved light harvesting efficiency (LHE) values as compared to Y123, highlighting their improved capacity to generate charge carriers by light absorption. With the exception of dye A4, all newly developed dyes might have a superior rate of charge carrier mobility than R, according to reorganization energies λre. Dyes A3 and A4 had the greatest open-circuit voltage (Voc). Dye A3 exhibited improvement in all of its examined properties, making it a promising choice in DSSC applications.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

Data availability

All data generated or analyzed during this study are included in this published article and its supplementary information file.

Code availability

Gaussian 09 W and GaussView 5.1 are used for simulation, and origin software is used to draw the plots.

References  

  1. Shahsavari A, Akbari M (2018) Potential of solar energy in developing countries for reducing energy-related emissions. Renew Sustain Energy Rev 90:275–291. https://doi.org/10.1016/j.rser.2018.03.065

    Article  CAS  Google Scholar 

  2. Karakurt I, Aydin G (2023) Development of regression models to forecast the CO2 emissions from fossil fuels in the BRICS and MINT countries. Energy 263:125650. https://doi.org/10.1016/j.energy.2022.125650

    Article  CAS  Google Scholar 

  3. Gereffi G, Dubay K, Robinson J, others (2008) Concentrating solar power clean energy for the electric grid by

  4. Perez M, Perez R (2022) Update 2022–A fundamental look at supply side energy reserves for the planet. Sol Energy Adv 2:100014. https://doi.org/10.1016/j.seja.2022.100014

    Article  Google Scholar 

  5. Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photonics 8:506–514. https://doi.org/10.1038/nphoton.2014.134

    Article  CAS  Google Scholar 

  6. Kan B, Kan Y, Zuo L et al (2021) Recent progress on all-small molecule organic solar cells using small-molecule nonfullerene acceptors. InfoMat 3:175–200

    Article  CAS  Google Scholar 

  7. Rand BP, Cheyns D, Vasseur K et al (2012) The impact of molecular orientation on the photovoltaic properties of a phthalocyanine/fullerene heterojunction. Adv Funct Mater 22:2987–2995

    Article  CAS  Google Scholar 

  8. Li Y, Huang W, Zhao D et al (2022) Recent progress in organic solar cells: a review on materials from acceptor to donor. Molecules 27:1800. https://doi.org/10.3390/molecules27061800

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Breitung EM, Shu C-F, McMahon RJ (2000) Thiazole and thiophene analogues of donor- acceptor stilbenes: molecular hyperpolarizabilities and structure- property relationships. J Am Chem Soc 122:1154–1160

    Article  CAS  Google Scholar 

  10. Hagfeldt A, Boschloo G, Sun L et al (2010) Dye-sensitized solar cells. Chem Rev 110:6595–6663. https://doi.org/10.1021/cr900356p

    Article  CAS  PubMed  Google Scholar 

  11. Dey S (2019) Recent progress in molecular design of fused ring electron acceptors for organic solar cells. Small 15:1900134

    Article  Google Scholar 

  12. Zheng Z, Yao H, Ye L et al (2020) PBDB-T and its derivatives: a family of polymer donors enables over 17% efficiency in organic photovoltaics. Mater Today 35:115–130. https://doi.org/10.1016/j.mattod.2019.10.023

    Article  CAS  Google Scholar 

  13. Kang SB, Kim J-H, Jeong MH et al (2019) Stretchable and colorless freestanding microwire arrays for transparent solar cells with flexibility. Light Sci Appl 8:121. https://doi.org/10.1038/s41377-019-0234-y

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Hu Z, Wang J, Ma X et al (2020) A critical review on semitransparent organic solar cells. Nano Energy 78:105376. https://doi.org/10.1016/j.nanoen.2020.105376

    Article  CAS  Google Scholar 

  15. Horiuchi T, Miura H, Sumioka K, Uchida S (2004) High efficiency of dye-sensitized solar cells based on metal-free indoline dyes. J Am Chem Soc 126:12218–12219

    Article  CAS  PubMed  Google Scholar 

  16. Abe R, Shinmei K, Koumura N et al (2013) Visible-light-induced water splitting based on two-step photoexcitation between dye-sensitized layered niobate and tungsten oxide photocatalysts in the presence of a triiodide/iodide shuttle redox mediator. J Am Chem Soc 135:16872–16884. https://doi.org/10.1021/ja4048637

    Article  CAS  PubMed  Google Scholar 

  17. Kakiage K, Yamamura M, Fujimura E et al (2010) High performance of Si–O–Ti bonds for anchoring sensitizing dyes on TiO2 electrodes in dye-sensitized solar cells evidenced by using alkoxysilylazobenzenes. Chem Lett 39:260–262

    Article  CAS  Google Scholar 

  18. Ramsdale CM, Barker JA, Arias AC et al (2002) The origin of the open-circuit voltage in polyfluorene-based photovoltaic devices. J Appl Phys 92:4266–4270

    Article  CAS  Google Scholar 

  19. Hassan AU, Sumrra SH, Nkungli NK, Güleryüz C (2022) Theoretical probing of 3d nano metallic clusters as next generation non-linear optical materials. Results Chem 4:100627. https://doi.org/10.1016/j.rechem.2022.100627

    Article  CAS  Google Scholar 

  20. Hassan AU, Sumrra SH, Mustafa G et al (2023) Molecular modeling of mordant black dye for future applications as visible light harvesting materials with anchors: design and excited state dynamics. J Mol Model 29:74. https://doi.org/10.1007/s00894-023-05474-y

    Article  CAS  PubMed  Google Scholar 

  21. Frisch JM, Trucks WG, Schlegel BH et al (2013) Gaussian 09, Revision D. 01, Gaussian, Inc. Wallingford, CT

  22. Anthony JE (2011) Small-molecule, nonfullerene acceptors for polymer bulk heterojunction organic photovoltaics. Chem Mater 23:583–590

    Article  CAS  Google Scholar 

  23. Sumrra SH, Hassan AU, Zafar MN et al (2022) Metal incorporated sulfonamides as promising multidrug targets: combined enzyme inhibitory, antimicrobial, antioxidant and theoretical exploration. J Mol Struct 1250:131710. https://doi.org/10.1016/j.molstruc.2021.131710

    Article  CAS  Google Scholar 

  24. Li R, Liu J, Cai N et al (2010) Synchronously reduced surface states, charge recombination, and light absorption length for high-performance organic dye-sensitized solar cells. J Phys Chem B 114:4461–4464. https://doi.org/10.1021/jp101222s

    Article  CAS  PubMed  Google Scholar 

  25. Hassan AU, Sumrra SH, Mustafa G et al (2023) Creating intense and refined NLO responses by utilizing dual donor structural designs in A-π-D-π-D-π-A type organic switches: computed device parameters. Struct Chem. https://doi.org/10.1007/s11224-023-02138-8

  26. Lonnecke K, Eberhardt O, Wallmersperger T (2023) Electrostatic charge distribution in armchair and zigzag carbon nanotubes: a numerical comparison of CNT charge models. Acta Mech 234:1–16. https://doi.org/10.1007/s00707-021-03085-3

  27. Huang S, Shao W, Shi S et al (2022) The effect of conjugated groups for favourable molecular planarity and efficient suppression of charge recombination simultaneously of phenothiazine-based organic dyes for dye-sensitized solar cells. Synth Met 290:117137. https://doi.org/10.1016/j.synthmet.2022.117137

    Article  CAS  Google Scholar 

  28. Ye J-T, Wang H-Q, Zhang Y, Qiu Y-Q (2019) Regulation of the molecular architectures on second-order nonlinear optical response and thermally activated delayed fluorescence property: homoconjugation and twisted donor–acceptor. J Phys Chem C 124:921–931

    Article  Google Scholar 

  29. Kaur S, Mohiuddin G, Punjani V et al (2019) Structural organization and molecular self-assembly of a new class of polar and non-polar four-ring based bent-core molecules. J Mol Liq 295:111687

    Article  CAS  Google Scholar 

  30. Aydın G, Koçak O, Güleryüz C, Yavuz I (2020) Structural order and charge transfer in highly strained carbon nanobelts. New J Chem 44:15769–15775. https://doi.org/10.1039/D0NJ03455J

    Article  Google Scholar 

  31. Hassan AU, Sumrra SH, Imran M, Chohan ZH (2022) New 3d multifunctional metal chelates of sulfonamide: spectral, vibrational, molecular modeling, DFT, medicinal and in silico studies. J Mol Struct 1254:132305. https://doi.org/10.1016/j.molstruc.2021.132305

    Article  CAS  Google Scholar 

  32. Quiroz-Garcia B, Figueroa R, Cogordan JA, Delgado G (2005) Photocyclodimers from Z-ligustilide. Experimental results and FMO analysis. Tetrahedron Lett 46:3003–3006

    Article  CAS  Google Scholar 

  33. Friesen BA, Wiggins B, McHale JL et al (2010) Differing HOMO and LUMO mediated conduction in a porphyrin nanorod. J Am Chem Soc 132:8554–8556

    Article  CAS  PubMed  Google Scholar 

  34. Influence of energy gap between charge-transfer and locally excited states on organic long persistence luminescence | Nature Communications. https://www.nature.com/articles/s41467-019-14035-y. Accessed 19 Mar 2023

  35. Hassan AU, Sumrra SH, Zafar MN et al (2022) New organosulfur metallic compounds as potent drugs: synthesis, molecular modeling, spectral, antimicrobial, drug likeness and DFT analysis. Mol Divers 26:51–72. https://doi.org/10.1007/s11030-020-10157-4

    Article  CAS  PubMed  Google Scholar 

  36. Hassan AU, Mohyuddin A, Güleryüz C et al (2022) Novel pull–push organic switches with D–π–A structural designs: computational design of star shape organic materials. Struct Chem 34(2):399–412. https://doi.org/10.1007/s11224-022-01983-3

    Article  CAS  Google Scholar 

  37. Hassan AU, Sumrra SH, Zubair M et al (2022) Structurally modulated D-π-D-A(Semiconductor) anchoring dyes to enhance the tunable NLO response: a DFT/TDDFT quest for new photovoltaic materials. Struct Chem 34(3):1043–1060. https://doi.org/10.1007/s11224-022-02070-3

    Article  CAS  Google Scholar 

  38. Yu J, Cui Y, Wu C et al (2012) Second-order nonlinear optical activity induced by ordered dipolar chromophores confined in the pores of an anionic metal–organic framework. Angew Chem 124:10694–10697

    Article  Google Scholar 

  39. Durand RJ, Achelle S, Gauthier S et al (2018) Incorporation of a ferrocene unit in the $π$-conjugated structure of donor-linker-acceptor (D-$π$-A) chromophores for nonlinear optics (NLO). Dyes Pigments 155:68–74

  40. Yahya M, Nural Y, Seferoğlu Z (2022) Recent advances in the nonlinear optical (NLO) properties of phthalocyanines: a review. Dyes Pig 198:109. https://doi.org/10.1016/j.dyepig.2021.109960

    Article  CAS  Google Scholar 

  41. Hlel A, Mabrouk A, Chemek M et al (2015) A DFT study of charge-transfer and opto-electronic properties of some new materials involving carbazole units. Comput Condens Matter 3:30–40

    Article  Google Scholar 

  42. Norman P, Bishop DM, Jensen HJA, Oddershede J (2005) Nonlinear response theory with relaxation: the first-order hyperpolarizability. J Chem Phys 123:194103

    Article  PubMed  Google Scholar 

  43. Sahki FA, Bouraiou A, Taboukhat S et al (2021) Design and synthesis of highly conjugated electronic phenanthrolines derivatives for remarkable NLO properties and DFT analysis. Optik 241:166. https://doi.org/10.1016/j.ijleo.2021.166949

    Article  CAS  Google Scholar 

  44. Hassan AU, Mohyuddin A, Nadeem S et al (2022) Structural and electronic (absorption and fluorescence) properties of a stable triplet diphenylcarbene: a DFT study. J Fluoresc 32(5):1629–1638. https://doi.org/10.1007/s10895-022-02969-4

    Article  CAS  PubMed  Google Scholar 

  45. Chen C-Y, Wang M, Li J-Y et al (2009) Highly efficient light-harvesting ruthenium sensitizer for thin-film dye-sensitized solar cells. ACS Nano 3:3103–3109

    Article  CAS  PubMed  Google Scholar 

  46. Hassan AU, Sumrra SH (2022) Exploration of pull–push effect for novel photovoltaic dyes with A–π–D design: A DFT/TD-DFT investigation. J Fluoresc 32(6):1999–2014. https://doi.org/10.1007/s10895-022-03003-3

    Article  CAS  PubMed  Google Scholar 

  47. Singh Y, Patel RN, Patel SK et al (2019) Experimental and quantum computational study of two new bridged copper(II) coordination complexes as possible models for antioxidant superoxide dismutase: molecular structures, X-band electron paramagnetic spectra and cryogenic magnetic properties. Polyhedron 171:155–171. https://doi.org/10.1016/j.poly.2019.07.015

    Article  CAS  Google Scholar 

  48. Hassan AU, Sumrra SH, Nazar MF, Güleryüz C (2022) A DFT study on new photovoltaic dyes to investigate their NLO tuning at near infrared region (NIR) as pull–push effect by end capped acceptors. J Fluoresc. https://doi.org/10.1007/s10895-022-03075-1

    Article  PubMed  PubMed Central  Google Scholar 

  49. Galkowski K, Mitioglu A, Miyata A et al (2016) Determination of the exciton binding energy and effective masses for methylammonium and formamidinium lead tri-halide perovskite semiconductors. Energy Environ Sci 9:962–970. https://doi.org/10.1039/C5EE03435C

    Article  CAS  Google Scholar 

  50. Hassan AU, Sumrra SH, Zafar W et al (2022) Enriching the compositional tailoring of NLO responsive dyes with diversity oriented electron acceptors as visible light harvesters: a DFT/TD-DFT approach. Mol Phys 121(1):e2148585. https://doi.org/10.1080/00268976.2022.2148585

    Article  CAS  Google Scholar 

  51. Mary SJJ, Siddique MUM, Pradhan S et al (2020) Quantum chemical insight into molecular structure, NBO analysis of the hydrogen-bonded interactions, spectroscopic (FT--IR, FT--Raman), drug likeness and molecular docking of the novel anti COVID-19 molecule 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(4-fluorophenyl)acetamide - dimer. Spectrochim Acta A Mol Biomol Spectrosc 244:118825. https://doi.org/10.1016/j.saa.2020.118825

  52. Sumrra SH, Arshad Z, Zafar W et al (2022) Metal incorporated aminothiazole-derived compounds: synthesis, density function theory analysis, in vitro antibacterial and antioxidant evaluation. R Soc Open Sci 8:210910. https://doi.org/10.1098/rsos.210910

    Article  CAS  Google Scholar 

  53. Hassan AU, Sumrra SH (2022) Exploring the bioactive sites of new sulfonamide metal chelates for multi-drug resistance: an experimental versus theoretical design. J Inorg Organomet Polym Mater 32:513–535. https://doi.org/10.1007/s10904-021-02135-6

    Article  CAS  Google Scholar 

  54. Hassan AU, Sumrra SH, Mustafa G, Noreen S, Ali A, Sara S, Imran M (2023) Enhancing NLO performance by utilizing tyrian purple dye as donor moiety in organic DSSCs with end capped acceptors: A theoretical study. J Mol Graph Model 124:108538. https://doi.org/10.1016/j.jmgm.2023.108538

Download references

Acknowledgements

The authors are grateful to the University of Gujrat, Gujrat, Pakistan, for the access to all research facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Gujrat, Gujrat, 50700, Pakistan

    Abrar U. Hassan, Sajjad H. Sumrra & Sadaf Noreen

  2. Department of Biochemistry and Biotechnology, University of Gujrat, Gujrat, 50700, Pakistan

    Muddassar Zafar

  3. Department of Chemistry, University of Management and Technology Lahore, C-II, Johar Town, Lahore, 5476, Pakistan

    Ayesha Mohyuddin

  4. Department of Opticianry, Altınbaş University, Istanbul, 34144, Turkey

    Cihat Güleryüz

Authors
  1. Abrar U. Hassan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sajjad H. Sumrra
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Muddassar Zafar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ayesha Mohyuddin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sadaf Noreen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Cihat Güleryüz
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Conceptualization: Sajjad H. Sumrra; methodology: Abrar U. Hassan; formal analysis: Ayesha Mohyuddin; investigation: Muddassar Zafar; writing—original draft preparation: Sadaf Noreen; writing—review and editing: Cihat Güleryüz; resources: Sajjad H. Sumrra.

Corresponding authors

Correspondence to Abrar U. Hassan or Sajjad H. Sumrra.

Ethics declarations

Ethics approval

This work did not involve any human subjects.

Consent to participate

This article does not have any studies with human participants or animals, clinical trial registration, or plant reproducibility performed by any author.

Consent for publication

All authors have approved the paper and agree with its publication.

Competing interests

The authors declare no competing interests.

Additional information

Publisher's note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 212 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hassan, A.U., Sumrra, S.H., Zafar, M. et al. DFT-guided structural modeling of end-group acceptors at Y123 core for sensitizers as high-performance organic solar dyes and NLO responses. J Mol Model 29, 262 (2023). https://doi.org/10.1007/s00894-023-05668-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00894-023-05668-4

Keywords

Search

Navigation