Skip to main content
SpringerLink
Log in

Design, synthesis, and comparative study of optoelectronic properties of arylated triazine-based sulfanilamide derivatives through Suzuki–Miyaura cross-coupling reactions

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

Abstract 

In this study, a series of arylated triazine–based sulfanilamide derivatives was designed and synthesized via palladium (Pd-0)-catalyzed, Suzuki–Miyaura cross-coupling. The theoretical investigation of the optoelectronic attributes of the synthesized compounds was accomplished using Gaussian-09 package by Density Functional Theory (DFT) approach at WB97XD/6-31G (d, p). The triazine core was stabilized by the electron-rich environment around the HOMO orbital which in turn ensured the availibity of electrons for complexation of the Pd center. The computations in DFT were carried out for better comprehension of structure–property relationship. The theoretically computed values were in good agreement with the experimental findings. The outcomes of this investigation validated importance of mono- and di-substituted arylated triazine–based sulfanilamide derivatives in organic electronics. The structural identity of newly synthesized compounds was confirmed by 1H NMR, 13C NMR, and EI-MS analyses.

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
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

Data availability

All data will be available if required.

Code availability

Not applicable.

References

  1. Machakanur SS et al (2012) Synthesis, characterization and anticancer evaluation of novel tri-arm star shaped 1, 3, 5-triazine hydrazones. J Mol Struct 1011:121–127

    Article  CAS  Google Scholar 

  2. Vielhaber G et al (2006) Sunscreens with an absorption maximum of≥ 360 nm provide optimal protection against UVA1-induced expression of matrix metalloproteinase-1, interleukin-1, and interleukin-6 in human dermal fibroblasts. Photochem Photobiol Sci 5(3):275–282

    Article  CAS  PubMed  Google Scholar 

  3. Tanaka H et al (2012) Efficient green thermally activated delayed fluorescence (TADF) from a phenoxazine–triphenyltriazine (PXZ–TRZ) derivative. Chem Commun 48(93):11392–11394

    Article  CAS  Google Scholar 

  4. Gamez P, Reedijk J (2006) 1, 3, 5-Triazine-based synthons in supramolecular chemistry. Eur J Inorg Chem 2006(1):29–42

    Article  Google Scholar 

  5. Afonso CA, Lourenço NM, Rosatella ADA (2006) Synthesis of 2, 4, 6-tri-substituted-1, 3, 5-triazines. Molecules 11(1):81–102

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Wang C et al (2017) A sequential suzuki coupling approach to unsymmetrical aryl s-triazines from cyanuric chloride. Adv Synth Catal 359(14):2514–2519

    Article  CAS  Google Scholar 

  7. Tan JQ, Chang JH, Deng MZ (2004) Coupling reaction of organoboronic acids with chloropyrimidines and trichlorotriazine. Chin J Chem 22(9):941–944

    Article  CAS  Google Scholar 

  8. Cammidge AN, Crépy KV (2000) The first asymmetric Suzuki cross-coupling reaction. Chem Commun 18:1723–1724

    Article  Google Scholar 

  9. Karimi B, Safari AA (2008) One-pot synthesis of α-aminonitriles using a highly efficient and recyclable silica-based scandium (III) interphase catalyst. J Organomet Chem 693(18):2967–2970

    Article  CAS  Google Scholar 

  10. Kertesz M, Choi CH, Yang S (2005) Conjugated polymers and aromaticity. Chem Rev 105(10):3448–3481

    Article  CAS  PubMed  Google Scholar 

  11. Veerakumar P et al (2017) Computational studies of versatile heterogeneous palladium-catalyzed Suzuki, Heck, and Sonogashira coupling reactions. ACS Sustain Chem Eng 5(10):8475–8490

    Article  CAS  Google Scholar 

  12. Sun Y et al (2012) Solution-processed small-molecule solar cells with 6.7% efficiency. Nature Mater 11(1):44–48

    Article  CAS  Google Scholar 

  13. Naveed A et al (2022) Tuning the optoelectronic properties of benzodithiophene based donor materials and their photovoltaic applications. Mater Sci SemicondProcess 137:106150

    CAS  Google Scholar 

  14. Zara Z et al (2017) A comparative study of DFT calculated and experimental UV/Visible spectra for thirty carboline and carbazole based compounds. J Mol Struct 1149:282–298

    Article  CAS  Google Scholar 

  15. Khera, N., et al. Design of charge controller for solar PV systems. in 2015 International Conference on Control, Instrumentation, Communication and Computational Technologies (ICCICCT). 2015. IEEE.

  16. Funes-Ardoiz I, Maseras F (2018) Oxidative coupling mechanisms: current state of understanding. ACS Catal 8(2):1161–1172

    Article  CAS  Google Scholar 

  17. Hosseinnejad T, Ebrahimpour-Malmir F, Fattahi B (2018) Computational investigations of click-derived 1, 2, 3-triazoles as keystone ligands for complexation with transition metals: a review. RSC Adv 8(22):12232–12259

    Article  CAS  Google Scholar 

  18. Mubashar U et al (2021) Designing and theoretical study of fluorinated small molecule donor materials for organic solar cells. J Mol Model 27(7):1–13

    Article  Google Scholar 

  19. Salim M et al (2021) Tuning the optoelectronic properties of ZOPTAN core-based derivatives by varying acceptors to increase efficiency of organic solar cell. J Mol Model 27(11):1–14

    Article  Google Scholar 

  20. Yousaf I et al (2021) Isatin-derived non-fullerene acceptors for efficient organic solar cells. Mater Sci Semicond Process 121:105345

    Article  CAS  Google Scholar 

  21. Farhat A et al (2021) Designing and theoretical characterization of benzodithiophene dione based donor molecules for small molecule organic solar cells. Optik 242:167098

    Article  CAS  Google Scholar 

  22. Musawwir A et al (2021) Theoretical and computational study on electronic effect caused by electron withdrawing/electron-donating groups upon the coumarin thiourea derivatives. Comput Theor Chem 1201:113271

    Article  CAS  Google Scholar 

  23. Sikandar R et al (2021) Tuning the optoelectronic properties of oligothienyl silane derivatives and their photovoltaic properties. J Mol Graph Model 106:107918

    Article  CAS  PubMed  Google Scholar 

  24. Khan AU et al (2021) DFT study of superhalogen (AlF4) doped boron nitride for tuning their nonlinear optical properties. Optik 231:166464

    Article  CAS  Google Scholar 

  25. Dennington, R., et al., Semichem Inc. Shawnee Mission KS, GaussView, Version, 2009. 5.

  26. Martin JM, Bauschlicher CW Jr, Ricca A (2001) On the integration accuracy in molecular density functional theory calculations using Gaussian basis sets. Comput Phys Commun 133(2–3):189–201

    Article  CAS  Google Scholar 

  27. Rouf SA, Mares J, Vaara J (2015) 1H chemical shifts in paramagnetic Co (II) pyrazolylborate complexes: A first-principles study. J Chem Theory Comput 11(4):1683–1691

    Article  CAS  PubMed  Google Scholar 

  28. Wei L et al (2016) Application of Gaussian 09/GaussView 5.0 in analytical chemistry teaching. J Kunming Med Univ 37(10):134–136

    CAS  Google Scholar 

  29. Beck AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98(7):5648–6

    Article  Google Scholar 

  30. Corral I et al (2006) An experimental and theoretical investigation of gas-phase reactions of Ca2+ with glycine. Chem-A Eur J 12(26):6787–6796

    Article  CAS  Google Scholar 

  31. Irfan M et al (2017) Benchmark study of UV/Visible spectra of coumarin derivatives by computational approach. J Mol Struct 1130:603–616

    Article  CAS  Google Scholar 

  32. Bari A et al (2017) Benchmark study of bond dissociation energy of SiX (XF, Cl, Br, N, O, H and C) bond using density functional theory (DFT). J Mol Struct 1143:8–19

    Article  Google Scholar 

  33. Pedone A (2013) Role of solvent on charge transfer in 7-aminocoumarin dyes: new hints from TD-CAM-B3LYP and state specific PCM calculations. J Chem Theory Comput 9(9):4087–4096

    Article  CAS  PubMed  Google Scholar 

  34. Carta F et al (2011) Sulfonamides incorporating 1, 3, 5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: solution and X-ray crystallographic studies. Bioorg Med Chem 19(10):3105–3119

    Article  CAS  PubMed  Google Scholar 

  35. Hussain M et al (2010) Synthesis of aryl-substituted pyrimidines by site-selective suzuki–miyura cross-coupling reactions of 2, 4, 5, 6-tetrachloropyrimidine. Adv Synth Catal 352(9):1429–1433

    Article  CAS  Google Scholar 

  36. Ullah I et al (2009) Synthesis of tetraaryl-p-benzoquinones by Suzuki-Miyaura cross-coupling reactions of tetrabromo-p-benzoquinone. Tetrahedron Lett 50(32):4651–4653

    Article  CAS  Google Scholar 

  37. Hussain M et al (2015) Synthesis of arylated benzofurans by regioselective Suzuki-Miyaura Cross-coupling reactions of 2, 3-dibromobenzofurans-and 2, 3, 5-tribromobenzofurans. J Heterocycl Chem 52(2):497–505

    Article  CAS  Google Scholar 

  38. Khera RA et al (2012) Regioselective arylation and alkynylation of 2, 3-dibromo-1H-inden-1-one by Suzuki Miyaura and Sonogashira Cross-Coupling Reactions. Helv Chim Acta 95(3):469–482

    Article  CAS  Google Scholar 

  39. Khera RA et al (2012) Site-selective suzuki–Miyaura and Sonogashira Cross coupling reactions of the bis (triflate) of 2, 4′-bis (hydroxy) diphenyl sulfone. ChemCatChem 4(3):356

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Khera RA et al (2012) Synthesis of functionalized 3, 4-diarylbenzophenones and 2, 4-diarylbenzophenones by site-selective suzuki and sonogashira cross-coupling reactions of bis (triflates) of 3, 4-and 2, 4-dihydroxybenzophenone. Synthesis 44(02):219–234

    CAS  Google Scholar 

  41. Tognetti V et al (2013) A proposal for an extended dual descriptor: a possible solution when frontier molecular orbital theory fails. Phys Chem Chem Phys 15(34):14465–14475

    Article  CAS  PubMed  Google Scholar 

  42. Zhuo LG, Liao W, Yu ZX (2012) A frontier molecular orbital theory approach to understanding the Mayr equation and to quantifying nucleophilicity and electrophilicity by using HOMO and LUMO energies. Asian J Org Chem 1(4):336–345

    Article  CAS  Google Scholar 

  43. Fukui K, Yonezawa T, Shingu H (1952) A molecular orbital theory of reactivity in aromatic hydrocarbons. J Chem Phys 20(4):722–725

    Article  CAS  Google Scholar 

  44. Bendjeddou, A., et al., Molecular structure, HOMO-LUMO, MEP and Fukui function analysis of some TTF-donor substituted molecules using DFT (B3LYP) calculations. Int Res J Pure Appl Chem, 2016 1–9

  45. Marahatta AB (2020) Computational study on electronic structure, atomic charges distribution and frontier molecular orbitals of butadiene: general features for diels-alder reaction. Int J Progress Sci Technol 19(2):48–64

    Google Scholar 

  46. Marahatta AB (2020) DFT study on electronic charge distribution and quantum− chemical descriptors for the kinetic stability of vanadium aquo complex ions [V (H2O) 6] 2+ and [V (H2O) 6] 3+. Int J Progress Sci Technol 22(1):67–81

    Google Scholar 

  47. Demircioğlu Z, Kaştaş ÇA, Büyükgüngör O (2015) Theoretical analysis (NBO, NPA, Mulliken Population Method) and molecular orbital studies (hardness, chemical potential, electrophilicity and Fukui function analysis) of (E)-2-((4-hydroxy-2-methylphenylimino) methyl)-3-methoxyphenol. J Mol Struct 1091:183–195

    Article  Google Scholar 

  48. Saranya M et al (2018) Molecular structure, NBO and HOMO-LUMO analysis of quercetin on single layer graphene by density functional theory. Dig J Nanomater Biostruct 13(1):97–105

    Google Scholar 

Download references

Acknowledgements

Financial support from the Higher Education Commission (HEC) of Pakistan for this project is gratefully appreciated. We are also thankful to Dr. Khurshid Ayub, COMSATS University, Islamabad, Abbottabad Campus, Pakistan for additional resources.

Funding

Funding acquisition is from the University of Agriculture Faisalabad (UAF), Pakistan.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Agriculture, Faisalabad, 38040, Pakistan

    Iqra Khalid, Rasheed Ahmad Khera & Shauakt Ali

  2. Department of Biochemistry, University of Agriculture, Faisalabad, 38040, Pakistan

    Muhammad Shahid

Authors
  1. Iqra Khalid
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rasheed Ahmad Khera
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shauakt Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Muhammad Shahid
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Iqra Khalid: writing an original draft, formal analysis. Rasheed Ahmad Khera: data curation and funding acquisition Shauakt Ali: formal analysis, data curation. Muhammad Shahid: data curation and formal analysis.

Corresponding author

Correspondence to Rasheed Ahmad Khera.

Ethics declarations

Ethics approval

We approved all ethics.

Consent to participate

Not applicable.

Consent to publications

Not applicable.

Conflict of interest

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.

Associated information

Supporting information of all synthesized and optimized molecules along X, Y, and Z-axis at by Gaussian 09 package by DFT approach at WB97XD/6-31G (d, p) basis set.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khalid, I., Khera, R.A., Ali, S. et al. Design, synthesis, and comparative study of optoelectronic properties of arylated triazine-based sulfanilamide derivatives through Suzuki–Miyaura cross-coupling reactions. J Mol Model 28, 44 (2022). https://doi.org/10.1007/s00894-022-05027-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00894-022-05027-9

Keywords

Search

Navigation