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Synthesis of meso-substituted porphyrins using sustainable chemical processes

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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César A. Henriques

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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Vanessa A. Tomé

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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Carolina S. Vinagreiro

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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Mário J. F. Calvete

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

SPP full member in good standing

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Janusz M. Dąbrowski

Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland

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Marta Piñeiro

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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Luis G. Arnaut

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

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and

Mariette M. Pereira

Corresponding author

CQC, Department of Chemistry, Faculty of Science and Technology, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal

E-mail Address: [email protected]

SPP full member in good standing

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https://doi.org/10.1142/S1088424616300020Cited by:18

Abstract

The easy access and low price of pyrrole and aldehydes, conjugated with the simplicity in preparing meso-substituted porphyrins, makes this type of porphyrins very attractive for a broad range of applications. However, there is an increasing demand for the development of new synthetic processes involving more sustainable chemical principles substituting, whenever possible, dangerous organic solvents by alternative solvents, chromatographic purifications by precipitations and energy-intensive procedures by alternative energy sources such as microwaves and ultrasounds. In this review we will address some recent strategies to synthesize meso-substituted porphyrins using alternative energy sources, reaction media and catalysts, namely microwave irradiation, water as solvent, or solid microporous acid catalysts.

Dedicated to Professor Kevin M. Smith on the occasion of his 70th birthday

Keywords:

References

1. Die Chemie des Pyrrols, Vol. 1, Fischer H and Orth H. Akademische Verlagsgesellschaft: Leipzig, 1934. Google Scholar
2. The Colors of Life: An Introduction to the Chemistry of Porphyrins and Related Compounds, Milgrom LR. Oxford University Press: New York, 1997. Google Scholar
3. The Porphyrins, Vol. 1–7, Dolphin D. (Ed.) Academic Press: New York, 1979. Google Scholar
4. Serra VIV, Pires SMG, Alonso CMA, Neves MGPMS, Tome AC and Cavaleiro JAS. Topics Heterocycl. Chem. 2014; 33: 35–78. Google Scholar
5. Porphyrins and Metalloporphyrins, Smith KM. Elsevier Scientific Publishing Company: Amsterdam, 1975. Google Scholar
6. Smith KM and Vicente MGH. In Science of Synthesis, Vol. 17, Weinreb SM. (Ed.) Georg Thieme Verlag: Stuttgart, 2003. Google Scholar
7. The Porphyrin Handbook, Vol. 1–20, Kadish KMSmith KMGuilard R. (Eds.) Elsevier: Amsterdam, 1999–2003. Google Scholar
8. Handbook of Porphyrin Science, Vol. 1–35, Kadish KMSmith KMGuilard R. (Eds.) Academic Press: Boston, 2012–2014. Google Scholar
9. (a) Vicente MGH and Smith KM. Curr. Org. Synth. 2014; 11: 3–28. (b) Jensen TJ, Vicente MGH, Luguya R, Norton J, Fronczek FR and Smith KM. J. Photochem. Photobiol. B. 2010; 100: 100–111. (c) Mandoj F, Nardis S, Pomarico G, Stefanelli M, Schiaffino L, Ercolani G, Prodi L, Genovese D, Zaccheroni N, Fronczek FR, Smith KM, Xiao X, Shen J, Kadish KM and Paolesse R. Inorg. Chem. 2009; 48: 10346–10357. (d) Pandey RK, Zheng X, Dobhal MP and Smith KM. J. Porphyrins Phthalocyanines 2008; 12: 131–141. (e) Mwakwari C, Fronczek FR and Smith KM. Chem. Commun. 2007: 2258–2260. (f) Jiao L, Hao E, Fronczek FR, Smith KM and Vicente MGH. Tetrahedron 2007; 63: 4011–4017. (g) Song YJ, Haddad RE, Jia SL, Kok S, Olmstead MM, Nurco DJ, Schore NE, Zhang J, Ma JG and Smith KM. J. Am. Chem. Soc. 2005; 127: 1179–1192. (h) Vicente MGH and Smith KM. J. Porphyrins Phthalocyanines 2004; 8: 26–42. (i) Xie H, Leung SH and Smith KM.J. Porphyrins Phthalocyanines 2002; 6: 607–616. (j) Senge MO, Bischoff I, Nelson NY and Smith KM. J. Porphyrins Phthalocyanines 1999; 3: 99–116. (k) Gros CP, Jaquinod L, Khoury RG, Olmstead MM and Smith KM. J. Porphyrins Phthalocyanines 1997; 1: 201–212. (l) Senge MO, Medforth CJ, Forsyth TP, Lee DA, Olmstead MM, Jentzen W, Pandey RK, Shelnutt JA and Smith KM. Inorg. Chem. 1997; 36: 1149–1163. (m) Wallace DM, Leung SH, Senge MO and Smith KM. J. Org. Chem. 1993; 58: 7245–7257. (n) Sparks LD, Medforth CJ, Park MS, Chamberlain JR, Ondrias MR, Senge MO, Smith KM and Shelnutt JA. J. Am. Chem. Soc. 1993; 115: 581–592. (o) Medforth CJ, Senge MO, Smith KM, Sparks LD and Shelnutt JA. J. Am. Chem. Soc. 1992; 114: 9859–9869. (p) Pandey RK, Bellnier DA, Smith KM and Dougherty TJ. Photochem. Photobiol. 1991; 53: 65–72. (q) Barkigia KM, Berber MD, Fajer J, Medforth CJ, Renner MW and Smith KM. J. Am. Chem. Soc. 1990; 112: 8851–8857. (r) Minnetian OM, Morris IK, Snow KM and Smith KM. J. Org. Chem. 1989; 54: 5567–5574. Google Scholar
10. The Historie of the World by Sir Walter Raleigh, Raleigh W. Preface, 1614. Google Scholar
11. Li LL and Diau EWG. Chem. Soc. Rev. 2013; 42: 291–304. Crossref, ISI, Google Scholar
12. Walter MG, Rudine AB and Wamser CC. J. Porphyrins Phthalocyanines 2010; 14: 759–792. Link, ISI, Google Scholar
13. (a) Pinto SMA, Lourenco MAO, Calvete MJF, Abreu AR, Rosado MTS, Burrows HD and Pereira MM. Inorg. Chem. 2012; 50: 7916–7918. (b) Marques AT, Pinto SMA, Monteiro CJP, de Melo JSS, Burrows HD, Scherf U, Calvete MJF and Pereira MM. J. Polym. Sci. A1. 2012; 50: 1408–1417. (c) Monteiro CJP, Pina J, Pereira MM and Arnaut LG. Photochem. Photobiol. Sci. 2012; 7: 1233–1238. (d) Pinto SMA, Neves ACB, Calvete MJF, Abreu AR, Rosado MTS, Costa T, Burrows HD and Pereira MM. J. Photochem. Photobiol. A. 2012; 242: 59–66. (e) Monteiro CJP, Pereira MM, Vicente MGH and Arnaut LG. Tetrahedron 2012; 68: 8783–8788. (f) Calvete MJF, Int. Rev. Phys. Chem. 2012; 31: 319–366. (g) Henriques CA, Goncalves NPF, Abreu AR, Calvete MJF and Pereira MM. J. Porphyrins Phthalocyanines 2011; 15: 1–7. (h) Dini D, Meneghetti M, Calvete MJF, Arndt T, Liddiard C and Hanack M. Chem. Eur. J. 2010; 16: 1212–1220. (i) Pereira AMVM, Soares ARM, Calvete MJF and De la Torre G. J. Porphyrins Phthalocyanines 2009; 13: 419–428. (j) Dini D, Calvete M, Vagin S, Hanack M, Eriksson A and Lopes C. J. Porphyrins Phthalocyanines 2006; 10: 1165–1171. (k) Calvete MJF, Dini D, Hanack M, Sancho-Garcia JC, Chen WZ and Ji W. J. Mol. Model. 2006; 12: 543–550. (l) Dini D, Calvete MJF, Hanack M, Chen WZ and Ji W. Arkivoc 2006; 3: 77–96. Google Scholar
14. Mansuy D. C. R. Chim, 2007; 10: 392–413. Crossref, ISI, Google Scholar
15. Calvete MJF, Silva M, Pereira MM and Burrows HD. RSC Adv. 2013; 3: 22774–22789. Crossref, ISI, Google Scholar
16. (a) Silva M, Calvete MJF, Goncalves NPF, Burrows HD, Sarakha M, Fernandes A, Ribeiro MF, Azenha ME and Pereira MM, J. Hazard. Mater. 2012; 233–234: 79–88. (b) Pires SMG, Simões MMQ, Santos ICMS, Rebelo SLH, Pereira MM, Neves MGPMS and Cavaleiro JAS. Appl. Catal. A — Gen. 2012; 349: 51–56. Google Scholar
17. Silva M, Azenha ME, Pereira MM, Burrows HD, Sarakha M, Forano C, Ribeiro MF and Fernandes A. Appl. Catal. B: Environ. 2010; 100: 1–9. Crossref, ISI, Google Scholar
18. (a) Rebelo SLH, Pereira MM, Monsanto PV and Burrows HD. J. Mol. Catal. A — Chem. 2009; 297: 35–43. (b) Rebelo SLH, Melo A, Coimbra R, Azenha ME, Pereira MM, Burrows HD and Sarakha M. Environ. Chem. Lett. 2007; 5: 29–33. (c) Dąbrowski JM, Pucelik B, Pereira MM, Arnaut LG, Macyk W and Stochel G. RSC Adv. 2015; 5: 93252–93261. Google Scholar
19. (a) Dougherty TJ, Gomer CJ, Henderson BW, Jori G, Kessel D, Korbelik M, Moan J and Peng Q. J. Natl. Cancer Inst. 1998; 90: 889–905. (b) Giuntini F, Boyle R, Sibrian-Vazquez M and Vicente MGH, in The Handbook of Porphyrin Science (Ed: G.Ferreira), World Scientific Publishers, Singapore, 2013; 27: 303–416. (c) Manivannan E, Nayan JP and Pandey RK. In Porphyrin-Based Multifunctional Agents for Tumor-Imaging and Photodynamic Therapy (PDT), Vol. 4, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: Boston 2011; pp. 249–323. (d) Lovell JF, Liu TW, Chen J and Zheng G. Chem. Rev. 2010; 110: 2839–2857. (e) Vicente MGH. Curr. Med. Chem. 2001; 1: 175–194. (f) Ethirajan M, Chen Y, Joshi P and Pandey RK. Chem Soc Rev. 2011; 40: 340–362. Google Scholar
20. Calvete MJF, Simoes AVC, Henriques CA, Pinto SMA and Pereira MM. Curr. Org. Synth. 2014; 11: 127–140. Crossref, ISI, Google Scholar
21. Vinagreiro CS, Goncalves NPF, Calvete MJF, Schaberle FA, Arnaut LG and Pereira MM. J. Fluorine Chem. 2015; 180: 161–167. Crossref, ISI, Google Scholar
22. (a) Rocha LB, Gomes-da-Silva LC, Dąbrowski JM, Arnaut LG. Eur. J. Cancer, 2015; 51: 1822–1830. (b) Dąbrowski JM, Arnaut LG, Photochem. Photobiol. Sci. 2015; 14: 1765–1780. (c) Dąbrowski JM, Pucelik B, Pereira MM, Arnaut LG and Stochel G. J. Coord. Chem. 2015; 68: 3116–3134. (d) Saavedra R, Rocha LB, Dabrowski JM, Arnaut LG. ChemMedChem 2014; 9: 390–398. (e) Krzykawska-Serda M, Dabrowski JM, Arnaut LG, Szczygiel M, Urbanska K, G Stochel and Elas M. Free Rad. Biol. Med. 2014; 73: 239–251. (f) Arnaut LG, Pereira MM, Dabrowski JM, Silva EFF, Schaberle FA, Abreu AR, Rocha LB, Barsan MM, Urbanska K, Stochel G and Brett CMA. Chem. Eur. J. 2014; 20: 5346–5357. (g) Silva EFF, Serpa C, Dabrowski JM, Monteiro CJP, Formosinho SJ, Stochel G, Urbanska K, Simoes S, Pereira MM and Arnaut LG. Chem. Eur. J. 2010; 16: 9273–9286. (h) Monteiro CJP, Monteiro CJP, Pereira MM, Pinto SMA, Simoes AVC, Sa GFF, Arnaut LG, Formosinho SJ, Simoes S and Wyatt MF. Tetrahedron 2008; 64: 5132–5138. Google Scholar
23. Simoes AVC, Adamowicz A, Dabrowski JM, Calvete MJF, Abreu AR, Stochel G, Arnaut LG and Pereira MM. Tetrahedron 2012; 68: 8767–8772. Crossref, ISI, Google Scholar
24. (a) Goncalves NPF, Simoes AVC, Abreu AR, Abrunhosa AJ, Dabrowski JM and Pereira MM. J. Porphyrins Phthalocyanines 2015; 19: 946–955. (b) Monteiro CJP, Pereira MM, Goncalves NPF, Carvalho CG, Neves ACB, Abreu AR, Arnaut LG and Silva AMS. J. Porphyrins Phthalocyanines 2012; 16: 316–323. (c) Pereira MM, Monteiro CJP, Simoes AVC, Pinto SMA, Arnaut LG, Sa GFF, Silva EFF, Rocha LB, Simoes S and Formosinho SJ. J. Porphyrins Phthalocyanines 2009; 13: 567–573. Google Scholar
25. Pereira MM, Arnaut LG, Formosinho SJ and Monteiro CJP, Universidade de Coimbra PCT/EP/012212, 2005. Google Scholar
26. Pereira MM, Arnaut LG, Formosinho SJ, Monteiro CJP., WO Patent 053707, 2006. Google Scholar
27. Pereira MM, Abreu AR, Goncalves NPF, Calvete MJF, Simoes AVC, Monteiro CJP, Arnaut LG, Eusebio ME and Canotilho J. Green Chem. 2012; 14: 1666–1672. Crossref, ISI, Google Scholar
28. Vicente MGH and Smith KM. Curr. Org. Chem. 2000; 4: 139–174. Crossref, ISI, Google Scholar
29. Lindsey JS. Acc. Chem. Res. 2010; 43: 300–311. Crossref, ISI, Google Scholar
30. Pereira MM, Monteiro CJP and Peixoto AF. Targets in Heterocyclic Systems: Chemistry and Properties, Attanasi OASpinelli D. Eds; Italian Society of Chemistry, Vol 12, pp. 258–278. Google Scholar
31. Lindsey JS. In The Porphyrin Handbook, Vol. 1, Kadish KMSmith KMGuilard R. (Eds.) Academic Press: San Diego, CA, USA 2000; pp. 45–118. Google Scholar
32. Rothemund P. J. Am. Chem. Soc. 1935; 57: 2010–2011. Crossref, Google Scholar
33. Adler AD, Longo FR and Shergalis W. J. Am. Chem. Soc. 1964; 86: 3145–3149. Crossref, ISI, Google Scholar
34. Gonsalves AMDR, Varejao JMTB and Pereira MM. J. Heterocycl. Chem. 1991; 28: 635–640. Crossref, ISI, Google Scholar
35. Silva M, Fernandes A, Bebiano S, Calvete MJF, Ribeiro MF, Burrows HD and Pereira MM. Chem. Commun. 2014; 50: 6571–6573. Crossref, ISI, Google Scholar
36. (a) Henriques CA, Pinto SMA, Aquino GLB, Pineiro M, Calvete MJF and Pereira MM. ChemSusChem, 2014; 7: 2821–2824. (b) Henriques CA, Pinto SMA, Pineiro M, Canotilho J, Eusébio MES, Pereira MM and Calvete MJF. RSC Adv., 2015; 5: 64902–64910. Google Scholar
37. Gonsalves AMDR and Pereira MM. J. Heterocycl. Chem. 1985; 22: 931–933. Crossref, ISI, Google Scholar
38. Lindsey JS, Hsu HC and Schreimen IC. Tetrahedron Lett. 1986; 27: 4969–4970. Crossref, ISI, Google Scholar
39. Lindsey JS, Schreiman IC, Hsu HC, Kearney PC and Marguerettaz AM. J. Org. Chem. 1987; 52: 827–836. Crossref, ISI, Google Scholar
40. Wagner RW, Lawrence DS and Lindsey JS. Tetrahedron Lett. 1987; 28: 3069–3070. Crossref, ISI, Google Scholar
41. Johnstone RAW, Nunes MLPG, Pereira MM, Gonsalves AMDR and Serra AC. Heterocycles 1996; 43: 1423–1437. Crossref, ISI, Google Scholar
42. Green Chemistry Metrics, Measuring and Monitoring Sustainable Processes, Lapkin AConstable D. (Eds.) Wiley-Blackwell Publishing: Singapore, 2009. Google Scholar
43. Alternative Solvents for Green Chem, Kerton FM. The Royal Society of Chemistry: Cambridge, 2009. Google Scholar
44. Almeida C, Nascimento BFO, Pineiro M and Valente A. Colloids Surf. 2015; 480: 279–286. Crossref, Google Scholar
45. Chauhan SMS, Sahoo BB and Srinivas KA. Synth. Commun. 2001; 31: 33–37. Crossref, ISI, Google Scholar
46. Liu MO, Tai CH, Wang WY, Chen JR, Hu AT and Wei TH. J. Organomet. Chem. 2004; 689: 1078–1084. Crossref, ISI, Google Scholar
47. Cho TJ, Shreiner CD, Hwang SH, Moorefield CN, Courneya B, Godínez LA, Manríquez J, Jeong KU, Cheng SZD and Newkome GR. Chem. Commun. 2007; 4456–4458. Crossref, ISI, Google Scholar
48. McKay MG, Cwele T, Friedrich HB and Maguire GEM. Org. Biomol. Chem. 2009; 7: 3958–3968. Crossref, ISI, Google Scholar
49. Mikus A, Bielinska ME, Lipinska T and Ostrowski S. Synth. Commun. 2011; 41: 3703–3713. Crossref, ISI, Google Scholar
50. Nascimento BFO, Pineiro M, Rocha Gonsalves AMdA, Silva MR, Beja AM and Paixão JA. J. Porphyrins Phthalocyanines 2007; 11: 77–84. Link, ISI, Google Scholar
51. Nascimento BFO, Rocha Gonsalves AMdA and Pineiro M. Inorg. Chem. Commun. 2010; 13: 395–398. Crossref, ISI, Google Scholar
52. Lucas R, Vergnaud J, Teste K, Zerrouki R, Sol V and Krausz P. Tetrahedron Lett. 2008; 49: 5537–5539. Crossref, ISI, Google Scholar
53. Boens B, Faugeras PA, Vergnaud J, Lucas R, Teste K and Zerrouki R. Tetrahedron 2010; 66: 1994–1996. Crossref, ISI, Google Scholar
54. Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J and Korsakoff L. J. Org. Chem. 1967; 32: 476. Crossref, ISI, Google Scholar
55. Dallinger D and Kappe CO. Chem. Rev. 2007; 107: 2563–2591. Crossref, ISI, Google Scholar
56. Carr AG, Mammucari R and Foster NR. Chem. Eng. J. 2011; 172: 1–17. Crossref, ISI, Google Scholar
57. (a) Matthews E. In Microwave Synthesis; Chemistry at the Speed of Light, Hayes BL. (Ed.) CEM Publishing: Matthews NC, USA, 2002. (b) Kappe CO, Stadler A and Dalinger D. Microwaves in Organic and Medicinal Chemistry, 2nd ed., Wiley-VCH: Weinheim, 2012. (c) Kappe CO. Angew. Chem. 2004; 116: 6408–6443; Angew. Chem. Int. Ed. 2004; 43: 6250–6284. Google Scholar
58. Kremsner JM and Kappe CO. Eur. J. Org. Chem. 2005; 3672–3679. Crossref, ISI, Google Scholar
59. Colic M and Morse D. Colloids Surf. A 1999; 154: 167–178. Crossref, ISI, Google Scholar
60. Weingartner H and Franck EU. Angew. Chem. 2005; 117: 2730–2752; Angew. Chem. Int. Ed. 2005; 44: 2672–2692. Google Scholar
61. Purushothaman B, Varghese B and Bhyrappa P. Acta Cryst. C 2001; C57: 252–253. Crossref, ISI, Google Scholar
62. Bhyrappa P and Bhavana P. Chem. Phys. Lett. 2001; 349: 399–404. Crossref, ISI, Google Scholar
63. Gupta I and Ravikanth M. Tetrahedron 2003; 59: 6131–6139. Crossref, ISI, Google Scholar
64. Lapkin A and Constable D. Green Chemistry Metrics. Measuring and Monitoring Sustainable Processes, Wiley-Blackwell Publishing: Singapore, 2009. Google Scholar
65. Sheldon RA. J. Chem. Technol. Biotechnol. 1997; 68: 381–388. Crossref, ISI, Google Scholar
66. Van Aken K, Strekowski L and Patiny L. Beilstein J. Org. Chem. 2006; 2: 1–7. Crossref, ISI, Google Scholar
67. Hodgson GW and Baker BL. Nature 1967; 216: 29–32. Crossref, ISI, Google Scholar
68. (a) Silva M, Azenha ME, Pereira MM, Burrows HD, Sarakha M, Ribeiro MF, Fernandes A, Monsanto P and Castanheira F. Pure Appl. Chem. 2009; 81: 2025–2033. (b) Algarra F, Esteves MA, Fornés V, Garcia H and Primo J. New J. Chem. 1998; 22: 333–338. (c) Corma A and Garcia H. J. Chem. Soc., Dalton Trans. 2000; 1381–1394. (d) Rani VR, Kishan MR, Kulkarni SJ and Raghavan KV. Catal. Commun. 2005; 6: 531–538. (e) Nakagaki S, Xavier CR, Wosniak AJ, Mangrich AS, Wypych F, Cantão MP, Denicoló I and Kubota LT. Colloids Surf., A 2000; 168: 261–276. Google Scholar
69. Petit A, Loupy A, Maillard P and Momenteau M. Synth. Commun. 1992; 22: 1137–1142. Crossref, ISI, Google Scholar
70. Sharma RK, Ahuja G and Sidhwani IT. Green Chem. Lett. Rev. 2009; 2: 101–105. Crossref, ISI, Google Scholar
71. Yaseen M, Ali M, NajeebUllah M, Munawar MA and Khokhar I. J. Heterocyclic Chem. 2009; 46: 251–255. Crossref, ISI, Google Scholar
72. Vignaud Y, Granet R and Krausz P. J. Porphyrins Phthalocyanines 2006; 10: 937–941. Link, ISI, Google Scholar
73. Naik R, Joshi P, Kaiwar SP and Deshpande RK. Tetrahedron 2003; 59: 2207–2213. Crossref, ISI, Google Scholar
74. Onaka M, Shinoda T, Izumi Y and Nolen E. Tetrahedron Lett 1993; 34: 2625–2628. Crossref, ISI, Google Scholar
75. Onaka M, Shinoda T, Izumi Y and Nolen E. Chem. Lett. 1993; 22: 117–120. Crossref, ISI, Google Scholar
76. Shinoda T, Izumi Y and Onaka M. J. Chem. Soc., Chem. Commun. 1995; 1801–1802. Crossref, Google Scholar
77. Kishan MR, Rani VR, Murty MRVS, Devi PS, Kulkarni SJ and Raghavan KV. J. Mol. Catal. A: Chem. 2004; 223: 263–267. Crossref, ISI, Google Scholar
78. Kishan MR, Rani VR, Devi PS, Kulkarni SJ and Raghavan KV. J. Mol. Catal. A: Chem. 2007; 269: 30–34. Crossref, ISI, Google Scholar
79. Hoogenboom R, Wilms TFA, Erdmenger T and Schubert US. Aust. J. Chem. 2009; 62: 236–243. Crossref, ISI, Google Scholar
80. (a) Maugé F, Sahibed-Dine A, Gaillard M and Ziolek M. J. Catal. 2002; 207: 353–360. (b) Emeis CA. J. Catal. 1993; 141: 347–354. Google Scholar
81. Neya S and Funasaki N. J. Heterocycl. Chem. 1997; 34: 689–690. Crossref, ISI, Google Scholar
82. Gridnev AA and Nikiforov GA. Synth. Commun. 2009; 39: 1679–1689. Crossref, ISI, Google Scholar
83. Dalton J, Milgrom LR and Pemberton SM. J. Chem. Soc., Perkin Trans. 1980; 2: 370–372. Crossref, Google Scholar
84. Semeikin AS, Koifman OI and Berezin BD. Chem. Heterocycl. Compd. 1982; 18: 1046–1047. Crossref, Google Scholar
85. Fagadar-Cosma E, Enache C, Armeanu I and Fagadar-Cosma G. Digest J. Nanomat. Biostruct. 2007; 2: 175–183. ISI, Google Scholar
86. Ojadi ECA, Linschitz H, Gouterman M, Walter RI, Lindsey JS, Wagner RW, Droupadi PR and Wang W. J. Phys. Chem. 1993; 97: 13192–13197. Crossref, ISI, Google Scholar
87. Tjahjono DH, Akutsu T, Yoshioka N and Inoue H. Biochim. Biophys. Acta 1999; 1472: 333–343. Crossref, ISI, Google Scholar
88. Eaton SS and Eaton GR. J. Am. Chem. Soc. 1975; 97: 3660–3666. Crossref, ISI, Google Scholar
89. Wasserscheid P and Welton T. In Ionic Liquids in Synthesis, Wiley-VCH: Weinheim, 2008. Google Scholar
90. Kitaoka S, Nobuoka K and Ishikawa Y. Chem. Commun. 2004; 1902–1903. Crossref, ISI, Google Scholar
91. Kitaoka S, Nobuoka K and Ishikawa Y. Tetrahedron 2005; 61: 7678–7685. Crossref, ISI, Google Scholar
92. Kitaoka S, Nobuoka K, Hirakawa R, Ihara K and Ishikawa Y. Chem. Lett. 2013; 42 :1397–1399. Google Scholar
93. Kitaoka S, Nobuoka K, Hirakawa R, Ihara K and Ishikawa Y. RSC Adv. 2014; 4; 26777–26782. Crossref, ISI, Google Scholar
94. Babu MM, Amaravathi M, Giribabu L and Chandramouli G. J. Chem. Res. — S 2008; 11: 666–668. Crossref, ISI, Google Scholar
95. (a) Horváth IT and Anastas PT. Chem. Rev. 2007; 107: 2169–2173. (b) Dunn P, Wells A and Williams MT.Green Chemistry in the Pharmaceutical Industry, Wiley-VCH Publications: Weinheim, 2010. Google Scholar
96. Warner MG, Succaw GL and Hutchinson JE. Green Chem. 2001; 3: 267–270. Crossref, ISI, Google Scholar
97. Rothenberg G, Downie AP, Raston CL and Scott JL. J. Am. Chem. Soc. 2001; 123: 8701–8708. Crossref, ISI, Google Scholar
98. Tanaka K and Toda F. Chem. Rev. 2000; 100: 1025–1074. Crossref, ISI, Google Scholar
99. Drain CM and Gong X. Chem. Commun. 1997; 2117–2118. Crossref, ISI, Google Scholar
100. Nia S, Gong X, Drain CM, Jurow M, Rizvi W and Qureshy M. J. Porphyrins Phthalocyanines 2010; 14: 621–629. Link, ISI, Google Scholar
101. Shy H, Mackin P, Orvieto AS, Gharbharan D, Peterson GR, Bampos N and Hamilton TD. Faraday Discuss. 2014; 170: 59–69. Crossref, ISI, Google Scholar

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Received 13 November 2015

Accepted 16 December 2015
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Synthesis of meso-substituted porphyrins using sustainable chemical processes

Abstract

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