Advertisement

Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 1, pp 67–75 | Cite as

Synthetic access to new porphyrinoids from 2-nitro-5,10,15,20-tetraphenylporphyrin and an arylacetonitrile

  • Ouafa Amiri
  • Nuno M. M. MouraEmail author
  • Maria A. F. Faustino
  • José A. S. Cavaleiro
  • El Mostapha Rakib
  • Maria G. P. M. S. Neves
Original Paper
  • 63 Downloads

Abstract

In this work, the reactivity of 2-nitro-5,10,15,20-tetraphenylporphyrin with 2-(4-nitrophenyl)acetonitrile in the presence of KOH as base was studied. Under these conditions, three new compounds were isolated: a β-di-substituted derivative, as the major compound, accompanied by two minor products, a π-extended and a β-isoxazoline-fused derivative, all in acceptable yields. A preliminary study was also performed in the presence of K2CO3. It allowed the isolation of a cyclopropyl-annulated chlorin in very good yield. All the obtained products were photochemically and photophysically characterized, some of them showing promising properties to be used as photosensitizers in photodynamic processes.

Graphical abstract

Keywords

Tetrapyrroles Porphyrins Nucleophilic substitutions Photosensitizer Singlet oxygen 

Notes

Acknowledgements

Thanks are due to FCT/MEC for the financial support to the QOPNA research Unit (FCT UID/QUI/00062/2013), through national funds and when applicable co-financed by the FEDER, within the PT2020 Partnership Agreement and “Compete” 2020, and also to the Portuguese NMR Network. N. M. M. Moura thanks to FCT for his postdoctoral Grant (SFRH/BPD/84216/2012). The authors also thank the Transnational cooperation program, FCT-CNRST (Morocco), for financial assistance.

Supplementary material

706_2018_2283_MOESM1_ESM.docx (138.1 mb)
Supplementary material 1 (DOCX 141450 kb)

References

  1. 1.
    Kadish KM, Smith KM, Guilard R (2010) Handbook of Porphyrin Science. World Scientific Publishing Company Co, SingaporeGoogle Scholar
  2. 2.
    Di Carlo G, Biroli AO, Tessore F, Caramori S, Pizzotti M (2018) Coord Chem Rev 358:153CrossRefGoogle Scholar
  3. 3.
    Kundu S, Patra A (2017) Chem Rev 117:712CrossRefGoogle Scholar
  4. 4.
    Vamsi KN, Suman KJV, Madoori M, Seelam P, Lingamallu G (2017) Chemsuschem 10:4668CrossRefGoogle Scholar
  5. 5.
    Nakagaki S, Mantovani K, Sippel Machado G, de Freitas Dias, Castro K, Wypych F (2016) Molecules 21:291CrossRefGoogle Scholar
  6. 6.
    Costentin C, Robert M, Savéant J-M (2015) Acc Chem Res 48:2996CrossRefGoogle Scholar
  7. 7.
    Pegis ML, Wise CF, Martin DJ, Mayer JM (2018) Chem Rev 118:2340CrossRefGoogle Scholar
  8. 8.
    Zhang W, Lai W, Cao R (2017) Chem Rev 117:3717CrossRefGoogle Scholar
  9. 9.
    Jurow M, Schuckman AE, Batteas JD, Drain CM (2010) Coord Chem Rev 254:2297CrossRefGoogle Scholar
  10. 10.
    Niu T, Li A (2013) J Phys Chem Lett 4:4095CrossRefGoogle Scholar
  11. 11.
    Auwärter W, Écija D, Klappenberger F, Barth JV (2015) Nat Chem 7:105CrossRefGoogle Scholar
  12. 12.
    Lu H, Kobayashi N (2016) Chem Rev 116:6184CrossRefGoogle Scholar
  13. 13.
    Otsuki J (2018) J Mater Chem A 6:6710CrossRefGoogle Scholar
  14. 14.
    Paolesse R, Nardis S, Monti D, Stefanelli M, Di Natale C (2017) Chem Rev 117:2517CrossRefGoogle Scholar
  15. 15.
    Ding Y, Zhu W-H, Xie Y (2017) Chem Rev 117:2203CrossRefGoogle Scholar
  16. 16.
    Figueira F, Rodrigues JMM, Farinha AAS, Cavaleiro JAS, Tomé JPC (2016) J Porphyrins Phthalocyanines 20:950CrossRefGoogle Scholar
  17. 17.
    Singh S, Aggarwal A, Bhupathiraju NVSDK, Arianna G, Tiwari K, Drain CM (2015) Chem Rev 115:10261Google Scholar
  18. 18.
    Calvete MJF, Pinto SMA, Pereira MM, Geraldes CFGC (2017) Coord Chem Rev 333:82CrossRefGoogle Scholar
  19. 19.
    Zhou Y, Liang X, Dai Z (2016) Nanoscale 8:12394CrossRefGoogle Scholar
  20. 20.
    Diogo P, Fernandes C, Caramelo F, Mota M, Miranda IM, Faustino MAF, Neves MGPMS, Uliana MP, Santos JM, Gonçalves T (2017) Front Microbiol 8:498Google Scholar
  21. 21.
    Marciel L, Teles L, Moreira B, Pacheco M, Lourenço LMO, Neves MGPMS, Tomé JPC, Faustino MAF, Almeida A (2017) Future. Med Chem 9:365Google Scholar
  22. 22.
    Cerqueira A, Moura NMM, Serra VIV, Faustino MAF, Tomé AC, Cavaleiro JAS, Neves MGPMS (2017) Molecules 22:1269Google Scholar
  23. 23.
    Cavaleiro JAS, Tomé AC, Neves MGPMS (2010) Meso-tetraarylporphyrin derivatives: New synthetic methodologies. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science. World Scientific Publishing Company Co, Singapore, p 193Google Scholar
  24. 24.
    Serra VIV, Pires SMG, Alonso CMA, Neves MGPMS, Tomé AC, Cavaleiro JAS (2014) Meso-tetraarylporphyrins bearing nitro or amino groups: synthetic strategies and reactivity profiles. In: Paolesse R (ed) Synthesis and modifications of porphyrinoids. Springer, Berlin, p 35Google Scholar
  25. 25.
    Crossley MJ, King LG, Simpson JL (1997) J Chem Soc Perkin Trans 1 3087 and references herein citedGoogle Scholar
  26. 26.
    Jaquinod L (2000) Functionalization of 5,10,15,20-tetra-substituted porphyrins. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, San Diego, p 212Google Scholar
  27. 27.
    Jaquinod L, Gros C, Olmstead MM, Antolovich M, Smith KM (1996) Chem Commun 1475Google Scholar
  28. 28.
    Jaquinod L, Gros C, Khoury RG, Smith KM (1996) Chem Commun 2581Google Scholar
  29. 29.
    Luo D, Carter KA, Miranda D, Lovell JF (2017) Adv Sci 4:1600106CrossRefGoogle Scholar
  30. 30.
    Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) Chem Soc Rev 40:340CrossRefGoogle Scholar
  31. 31.
    Abrahamse H, Hamblin MR (2016) Biochem J 473:347CrossRefGoogle Scholar
  32. 32.
    Josefsen LB, Boyle RW (2012) Theranostics 2:916CrossRefGoogle Scholar
  33. 33.
    Gomes ATPC, Neves MGPMS, Cavaleiro JAS (2018) An Acad Bras Ciênc 90:993Google Scholar
  34. 34.
    Alves E, Faustino MAF, Neves MGPMS, Cunha Â, Nadais H, Almeida A (2015) J Photochem Photobiol C 22:34Google Scholar
  35. 35.
    Tim M (2015) J Photochem Photobiol B 150:2CrossRefGoogle Scholar
  36. 36.
    Rosa LP, Silva FC (2014) J Med Microb Diagn 3:158Google Scholar
  37. 37.
    Sperandio FF, Ying-Ying H, Hamblin MR (2013) Recent Pat Anti-Infect Drug Discov 8:108CrossRefGoogle Scholar
  38. 38.
    Adolfo VDM, Haynes MH, Ball AB, Tianhong D, Christos A, Kelso MJ, Hamblin MR, Tegos GP (2012) Photochem Photobiol 88:499CrossRefGoogle Scholar
  39. 39.
    Wainwright M, Maisch T, Nonell S, Plaetzer K, Almeida A, Tegos GP, Hamblin MR (2017) Lancet Infect Dis 17:e49CrossRefGoogle Scholar
  40. 40.
    Marko AJ, Patel NJ, Joshi P, Missert JR, Pandey RK (2016) In: Pandey RK, Kessel D, Dougherty TJ (eds) Handbook of photodynamic therapy—updates on recent applications of porphyrin-based compounds. World Scientific Publishing Co, Singapore, p 3CrossRefGoogle Scholar
  41. 41.
    van Straten D, Mashayekhi V, de Bruijn HS, Oliveira S, Robinson DJ (2017) Cancers 9:54CrossRefGoogle Scholar
  42. 42.
    Baptista MS, Cadet J, Di Mascio P, Ghogare AA, Greer A, Hamblin MR, Lorente G, Nunez SC, Ribeiro MS, Thomas AH, Vignoni M, Yoshimura TM (2017) Photochem Photobiol 93:912CrossRefGoogle Scholar
  43. 43.
    Yun SH, Kwok SJJ (2017) Nat Biomed Eng 1:16CrossRefGoogle Scholar
  44. 44.
    Baldwin JE, Crossley MJ, DeBernardis J (1982) Tetrahedron 38:685CrossRefGoogle Scholar
  45. 45.
    Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2005) Tetrahedron 61:11866Google Scholar
  46. 46.
    Faustino MA, Neves MGPMS, Vicente MGH, Silva AMS, Cavaleiro JS (1995) Tetrahedron Lett 36:5977Google Scholar
  47. 47.
    Batalha PN, Gomes ATPC, Forezi LSM, Costa L, de Souza MCBV, Boechat FdCS, Ferreira VF, Almeida A, Neves MGPMS, Cavaleiro JAS (2015) RSC Adv 5:71228Google Scholar
  48. 48.
    Bastos MM, Gomes ATPC, Neves MGPMS, Santos-Filho OA, Boechat N, Cavaleiro JAS (2013) Eur J Org Chem 1485Google Scholar
  49. 49.
    Hashimoto T, Choe Y-K, Nakano H, Hirao K (1999) J Phys Chem A 103:1894CrossRefGoogle Scholar
  50. 50.
    Baskin JS, Yu H-Z, Zewail AH (2002) J Phys Chem A 106:9837CrossRefGoogle Scholar
  51. 51.
    Durantini J, Otero L, Funes M, Durantini EN, Fungo F, Gervaldo M (2011) Electrochim Acta 56:4126CrossRefGoogle Scholar
  52. 52.
    Maximiano RV, Piovesan E, Zílio SC, Machado AEH, de Paula R, Cavaleiro JAS, Borissevitch IE, Ito AS, Gonçalves PJ, Neto NMB (2010) J Photochem Photobiol A 214:115CrossRefGoogle Scholar
  53. 53.
    Berlman IB (1971) Handbook of fluorescence spectra of aromatic molecules, 2nd edn. Academic, New YorkGoogle Scholar
  54. 54.
    Montalti AC, Prodi L, Gandolfi MT (2006) Handbook of photochemistryn, 3rd edn. Taylor & Francis, Boca RatonCrossRefGoogle Scholar
  55. 55.
    Spiller W, Kliesch H, Wöhrle D, Hackbarth S, Röder B, Schnurpfeil G (1998) J Porphyrins Phthalocyanines 2:145CrossRefGoogle Scholar
  56. 56.
    Zenkevich E, Sagun E, Knyukshto V, Shulga A, Mironov A, Efremova O, Bonnett R, Songca SP, Kassem M (1996) J Photochem Photobiol B 33:171CrossRefGoogle Scholar
  57. 57.
    Armarego WLF, Perrin DD (1996) Purification of laboratory chemicals, 4th edn. Butterworth-Heinemann, OxfordGoogle Scholar
  58. 58.
    Ermilov EA, Tannert S, Werncke T, Choi MTM, Ng DKP, Röder B (2006) Chem Phys 328:428CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Laboratoire de Chimie Organique et Analytique, Faculté des Sciences et TechniquesUniversité Sultan Moulay SlimaneBeni-MellalMorocco
  2. 2.QOPNA and Department of ChemistryUniversity of AveiroAveiroPortugal

Personalised recommendations