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

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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.

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References

  1. Kadish KM, Smith KM, Guilard R (2010) Handbook of Porphyrin Science. World Scientific Publishing Company Co, Singapore

    Google Scholar 

  2. Di Carlo G, Biroli AO, Tessore F, Caramori S, Pizzotti M (2018) Coord Chem Rev 358:153

    Article  Google Scholar 

  3. Kundu S, Patra A (2017) Chem Rev 117:712

    Article  CAS  Google Scholar 

  4. Vamsi KN, Suman KJV, Madoori M, Seelam P, Lingamallu G (2017) Chemsuschem 10:4668

    Article  Google Scholar 

  5. Nakagaki S, Mantovani K, Sippel Machado G, de Freitas Dias, Castro K, Wypych F (2016) Molecules 21:291

    Article  Google Scholar 

  6. Costentin C, Robert M, Savéant J-M (2015) Acc Chem Res 48:2996

    Article  CAS  Google Scholar 

  7. Pegis ML, Wise CF, Martin DJ, Mayer JM (2018) Chem Rev 118:2340

    Article  CAS  Google Scholar 

  8. Zhang W, Lai W, Cao R (2017) Chem Rev 117:3717

    Article  CAS  Google Scholar 

  9. Jurow M, Schuckman AE, Batteas JD, Drain CM (2010) Coord Chem Rev 254:2297

    Article  CAS  Google Scholar 

  10. Niu T, Li A (2013) J Phys Chem Lett 4:4095

    Article  CAS  Google Scholar 

  11. Auwärter W, Écija D, Klappenberger F, Barth JV (2015) Nat Chem 7:105

    Article  Google Scholar 

  12. Lu H, Kobayashi N (2016) Chem Rev 116:6184

    Article  CAS  Google Scholar 

  13. Otsuki J (2018) J Mater Chem A 6:6710

    Article  CAS  Google Scholar 

  14. Paolesse R, Nardis S, Monti D, Stefanelli M, Di Natale C (2017) Chem Rev 117:2517

    Article  CAS  Google Scholar 

  15. Ding Y, Zhu W-H, Xie Y (2017) Chem Rev 117:2203

    Article  CAS  Google Scholar 

  16. Figueira F, Rodrigues JMM, Farinha AAS, Cavaleiro JAS, Tomé JPC (2016) J Porphyrins Phthalocyanines 20:950

    Article  CAS  Google Scholar 

  17. Singh S, Aggarwal A, Bhupathiraju NVSDK, Arianna G, Tiwari K, Drain CM (2015) Chem Rev 115:10261

  18. Calvete MJF, Pinto SMA, Pereira MM, Geraldes CFGC (2017) Coord Chem Rev 333:82

    Article  CAS  Google Scholar 

  19. Zhou Y, Liang X, Dai Z (2016) Nanoscale 8:12394

    Article  CAS  Google Scholar 

  20. Diogo P, Fernandes C, Caramelo F, Mota M, Miranda IM, Faustino MAF, Neves MGPMS, Uliana MP, Santos JM, Gonçalves T (2017) Front Microbiol 8:498

  21. Marciel L, Teles L, Moreira B, Pacheco M, Lourenço LMO, Neves MGPMS, Tomé JPC, Faustino MAF, Almeida A (2017) Future. Med Chem 9:365

    CAS  Google Scholar 

  22. Cerqueira A, Moura NMM, Serra VIV, Faustino MAF, Tomé AC, Cavaleiro JAS, Neves MGPMS (2017) Molecules 22:1269

  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 193

    Google Scholar 

  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 35

    Google Scholar 

  25. Crossley MJ, King LG, Simpson JL (1997) J Chem Soc Perkin Trans 1 3087 and references herein cited

  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 212

    Google Scholar 

  27. Jaquinod L, Gros C, Olmstead MM, Antolovich M, Smith KM (1996) Chem Commun 1475

  28. Jaquinod L, Gros C, Khoury RG, Smith KM (1996) Chem Commun 2581

  29. Luo D, Carter KA, Miranda D, Lovell JF (2017) Adv Sci 4:1600106

    Article  Google Scholar 

  30. Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) Chem Soc Rev 40:340

    Article  CAS  Google Scholar 

  31. Abrahamse H, Hamblin MR (2016) Biochem J 473:347

    Article  CAS  Google Scholar 

  32. Josefsen LB, Boyle RW (2012) Theranostics 2:916

    Article  CAS  Google Scholar 

  33. Gomes ATPC, Neves MGPMS, Cavaleiro JAS (2018) An Acad Bras Ciênc 90:993

  34. Alves E, Faustino MAF, Neves MGPMS, Cunha Â, Nadais H, Almeida A (2015) J Photochem Photobiol C 22:34

  35. Tim M (2015) J Photochem Photobiol B 150:2

    Article  CAS  Google Scholar 

  36. Rosa LP, Silva FC (2014) J Med Microb Diagn 3:158

    Google Scholar 

  37. Sperandio FF, Ying-Ying H, Hamblin MR (2013) Recent Pat Anti-Infect Drug Discov 8:108

    Article  CAS  Google Scholar 

  38. Adolfo VDM, Haynes MH, Ball AB, Tianhong D, Christos A, Kelso MJ, Hamblin MR, Tegos GP (2012) Photochem Photobiol 88:499

    Article  Google Scholar 

  39. Wainwright M, Maisch T, Nonell S, Plaetzer K, Almeida A, Tegos GP, Hamblin MR (2017) Lancet Infect Dis 17:e49

    Article  Google Scholar 

  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 3

    Chapter  Google Scholar 

  41. van Straten D, Mashayekhi V, de Bruijn HS, Oliveira S, Robinson DJ (2017) Cancers 9:54

    Article  Google Scholar 

  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 93:912

    Article  CAS  Google Scholar 

  43. Yun SH, Kwok SJJ (2017) Nat Biomed Eng 1:16

    Article  Google Scholar 

  44. Baldwin JE, Crossley MJ, DeBernardis J (1982) Tetrahedron 38:685

    Article  CAS  Google Scholar 

  45. Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2005) Tetrahedron 61:11866

  46. Faustino MA, Neves MGPMS, Vicente MGH, Silva AMS, Cavaleiro JS (1995) Tetrahedron Lett 36:5977

  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 5:71228

  48. Bastos MM, Gomes ATPC, Neves MGPMS, Santos-Filho OA, Boechat N, Cavaleiro JAS (2013) Eur J Org Chem 1485

  49. Hashimoto T, Choe Y-K, Nakano H, Hirao K (1999) J Phys Chem A 103:1894

    Article  CAS  Google Scholar 

  50. Baskin JS, Yu H-Z, Zewail AH (2002) J Phys Chem A 106:9837

    Article  CAS  Google Scholar 

  51. Durantini J, Otero L, Funes M, Durantini EN, Fungo F, Gervaldo M (2011) Electrochim Acta 56:4126

    Article  CAS  Google Scholar 

  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 214:115

    Article  CAS  Google Scholar 

  53. Berlman IB (1971) Handbook of fluorescence spectra of aromatic molecules, 2nd edn. Academic, New York

    Google Scholar 

  54. Montalti AC, Prodi L, Gandolfi MT (2006) Handbook of photochemistryn, 3rd edn. Taylor & Francis, Boca Raton

    Book  Google Scholar 

  55. Spiller W, Kliesch H, Wöhrle D, Hackbarth S, Röder B, Schnurpfeil G (1998) J Porphyrins Phthalocyanines 2:145

    Article  CAS  Google Scholar 

  56. Zenkevich E, Sagun E, Knyukshto V, Shulga A, Mironov A, Efremova O, Bonnett R, Songca SP, Kassem M (1996) J Photochem Photobiol B 33:171

    Article  CAS  Google Scholar 

  57. Armarego WLF, Perrin DD (1996) Purification of laboratory chemicals, 4th edn. Butterworth-Heinemann, Oxford

    Google Scholar 

  58. Ermilov EA, Tannert S, Werncke T, Choi MTM, Ng DKP, Röder B (2006) Chem Phys 328:428

    Article  CAS  Google Scholar 

Download references

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.

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Authors and Affiliations

  1. Laboratoire de Chimie Organique et Analytique, Faculté des Sciences et Techniques, Université Sultan Moulay Slimane, BP 523, 2300, Beni-Mellal, Morocco

    Ouafa Amiri & El Mostapha Rakib

  2. QOPNA and Department of Chemistry, University of Aveiro, 3810-193, Aveiro, Portugal

    Ouafa Amiri, Nuno M. M. Moura, Maria A. F. Faustino, José A. S. Cavaleiro & Maria G. P. M. S. Neves

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  1. Ouafa Amiri
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  2. Nuno M. M. Moura
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  3. Maria A. F. Faustino
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  4. José A. S. Cavaleiro
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  5. El Mostapha Rakib
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  6. Maria G. P. M. S. Neves
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Correspondence to Nuno M. M. Moura.

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Amiri, O., Moura, N.M.M., Faustino, M.A.F. et al. Synthetic access to new porphyrinoids from 2-nitro-5,10,15,20-tetraphenylporphyrin and an arylacetonitrile. Monatsh Chem 150, 67–75 (2019). https://doi.org/10.1007/s00706-018-2283-y

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