How to cite this paper
Rahimi, R., Gholamrezapor, E., Naimi-Jamal, M & Rabbani, M. (2012). Oxidation of o-chloro and o-hydroxy benzyl alcohols catalyzed by copper (II) tetraphenylporphyrin nanoparticles synthesized by mixed solvent method.Current Chemistry Letters, 1(3), 101-108.
Refrences
1. Seko T., Ogura K., Kawakami Y., Sugino H., Toyotama H., Tanaka J. (1998) Excimer emission of anthracene, perylene, coronene and pyrene microcrystals dispersed in water. J. Chem .Phys. Lett., 291, 438-444.#
2. Wang Y., Deng K., Gui L., Tang Y., Zhou J.,Cai L., Qiu J., Ren D. (1999) Preparation and Characterization of Nanoscopic Organic Semiconductor of Oxovanadium Phthalocyanine. J. Colloid Interface. Sci., 213, 270-272.
3. Kasai H., Oikawa H., Okada S., Nakanishi H. (1998) Crystal Growth of Perylene Microcrystals in the Reprecipitation Method. Bull. Chem. Soc. Jpn. 71, 2597-2601.
4. Matsuda H., Yamada S., Keuren E. V., Katagi H., Kasai H., Okada S., Oikawa H., Nakanishi H., Smith E. C., Kar A. K., Wherrett B. S. (1997) Nonlinear refractive indexes of polydiacetylene microcrystals. Proc. SPIE., 2998, 241-248.
5. Tamaki Y., Asahi T., Masuharam H. (2000) Tailoring nanoparticles of aromatic and dye molecules by excimer laser irradiation. Appl. Surf. Sci., 168, 85-88.
6. Fu H. B., Yao J. N. (2001) Size Effects on the Optical Properties of Organic Nanoparticles. J. Am. Chem. Soc., 123, 1434-1439.
7. Fu H. B., Ji X. H., Yao J. N. (1999) The Size-dependent Property of 1,3,5-Triphenyl-2-pyrazoline Microcrystals. J. N. Chem. Lett., 9, 967-968.
8. Arun K. P., Prakriti R.B. (2008) Preparation and Characterization of free –standing pure porphyrin nanoparticles. J. Chem. Sci. 120, 485–491.
9. Zhong M. O., Hiroshi Y., Keisaku K. (2007) Preparation and optical properties of organic nanoparticles of porphyrin without self-aggregation. J. Photo. Chem. Photo. Bio. A: Chem., 189, 7-14.
10. Kashani-Motlagh M. M., Rahmatollah R., Javaheri-Kachousangi M. (2010) Ultrasonic method for the preparation of organic porphyrin nanoparticles, Molecules, 15, 280-287
11. Drain C. M., Nifiatis F., Vasenko A., Batteas J. D. (1998) Porphyrin tessellation by design: metal-mediated self-assembly of large arrays and tapes. Angew. Chem. Int. Ed. En., 37(17), 2344-2347.
12. Xu. W, Guo H., Akins D .L. (2001) Aggregation of Tetrakis(p-sulfonatophenyl) porphyrin within modified mesoporous MCM-41. J. Phys. Chem. B., 105, 1543-1546.
13. Akins D. L., Zhu H. R., Guo C. (1996) Aggregation of tetraaryl substitutedporphyrins in homogeneous solution. J. Phys. Chem., 100, 5420-5425.
14. Chou J. H., Kosal M. E., Nalwa H. S., Rakow N. A., Suslick K. S., Kadish K. M., Guilard R., Eds (2000) The porphyrin Handbook. Academic Press: New York, 6, 43-131.
15. Yoshiaki T., Tsuyoshi A., Hiroshi M. (2002) Nanoparticle formation of vanadyl phthalocyanine by laser ablation of its crystalline powder in a poor solvent. J. Phys. Chem. A, 106, 2135-2139.
16. Maiti N. C., Mazumdar S., Periasamy N. (1998) J- and H-Aggregates of porphyrin-surfactant complexes: time-resolved fluorescence and other spectroscopic studies. J. Phys. Chem. B, 102, 1528-1538.
17. Arun K. P., Prakriti R. B. (2008) Preparation and characterization of free–standing pure porphyrin nanoparticles. J. Chem. Sci., 120, 485-491.
18. Faulkner K. M., Liochev S. I., Fridovich I. (1994) Stable Mn(III) porphyrins mimic superoxide dismutase in vitro and substitute for it in vivo. J. Biol. Chem., 269 (38), 23471-23476
19. Xianchang G., Tatjana M., Chang X., James D. B. Charles M. D. (2002) Preparation and Characterization of Porphyrin Nanoparticles. J. Am. Chem. Soc., 124, 14290-14291.
20. Ghosh A., Selvamani T., Jose D. A., Das A., Mukhopadhyay I. (2007) Generation of nanostructures by the aggregation of porphyrin derivatives with long alkane chain in mix-solvent. J. Nanomater., Article ID 47234, doi:10.1155/2007/47234, 8 pages.
21. Debuigne F., Jeunieau L., Wiame M., Nagy J. B. (2000) Synthesis of Organic Nanoparticles in Different W/O Microemulsions. Langmuir, 16 (20), 7605-7611.
22. Tabushi I., Koga N. (1979) Synergetic combination of catalysis of the phase transfer-electron transfer type for the oxidation of alcohols or hydrocarbons. Tetrahedron Lett., 20, 3681-3684.
23. Labat G., Meunier B. (1989) Factors controlling the reactivity of a ligninase model based on the association of potassium monopersulfate to manganese and iron porphyrin complexes. J. Org. Chem., 54, 5008-5011.
24. Wietzerbin K., Meunier B., Bernadou J. (1997) Oxidation of tertiary diaryl alcohols catalyzed by a water-soluble metalloporphyrin: Caliph–Caliph versus Caliph–CAr bond cleavage. J. Chem. Commun., 23, 2321-2322.
25. Baciocchi E., Belvedere S. (1998) oxidation of ?-Alkylbenzyl Alcohols Catalysed by 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin Iron(III) Chloride Competition between C-H and C-C Bond Cleavage. Tetrahedron Lett., 39, 4711-4714.
26. Campestrini S., Cagnina A. (1999) A mechanistic study on oxidation of benzylic alcohols with PPh4HSO5catalysed by manganese_(III) porphyrins in homogeneous solution. J. Mol. Catal. A: Chem., 150, 77-86.
27. Moghadam M., Tangestaninejad S., Mirkhani V., Mohammadpoor-Baltork I. ,Kargar H. (2005) Mild and efficient oxidation of alcohols with sodium periodate catalyzed by polystyrene-bound Mn(III) porphyrin. Bioorg. Med. Chem., 13, 2901-2905.
28. Naik R., Joshi P., Deshpande R. K. (2005) Immobilization of metallporphyrins on polystyrene: Efficient catalysts for aerobic oxidation of alcohols. J. Mol. Catal. A: Chem., 238, 46-50.
29. Han J. H., Yoo S. K., Seo J. S., Hong S. J., Kim S. K., Kim C. (2005) Biomimetic alcohol oxidations by an iron(III) porphyrin complex: relevance to cytochrome P-450 catalytic oxidation and involvement of the two-state radical rebound mechanism. Dalton Trans., 2, 402-406.
30. Oh N. Y., Suh Y., Park M. J., Seo M. S., Kim J., Nam W. (2005) Mechanistic insight into alcohol oxidation by high-valent iron–oxo complexes of heme and nonheme ligands. Angew. Chem. Int. Ed., 44, 4235-4239.
31. Huang J. Y., Li S, J., Wang Y. G.(2006) TEMPO-linked metalloporphyrins as efficient catalysts for selective oxidation of alcohols and sulfides. Tetrahedron Lett., 47, 5637-5640.
32. Schults M. J., Sigman M. S. (2006) Recent advances in homogeneous transition metal-catalyzed aerobic alcohol oxidations. Tetrahedron, 62, 8227-8241.
33. Jiang N., Ragauskas A. J. (2007) Vanadium-catalyzed selective aerobic alcohol oxidation in ionic liquid [bmim]PF6 . Tetrahedron Lett., 48, 273-276.
34. Huang G., Luo J., Deng C. C., Guo Y. A., Zhao S. K.,Zhou H.,Wei S. (2008) Catalytic oxidation of toluene with molecular oxygen over manganese tetraphenylporphyrin supported on chitosan. Appl. Catal. A: Gen., 338, 83-86.
35. Yuan Y., Ji H., Chen Y., Han Y.,Song X., She Y., Zhong R. (2004) Oxidation of cyclohexane to adipic acid using fe-porphyrin as a biomimetic catalyst. Org. Process Res. Dev., 8, 418-420.
36. Zhou X. T., Ji H. B., Cheng Z., Xu J. C., Pei L. X., Wang L. F. (2007) Selective oxidation of sulfides to sulfoxides catalyzed by ruthenium(III) meso-tetraphenylporphyrin chloride in the presence of molecular oxygen. Bioorg. Med. Chem. Lett., 17, 4650-4653.
37. Jain S. L., sain B. (2001) Cobalt phthalocyanine tetrasulphonamide catalyzed aerobic oxidation of ?-hydroxyketones: an efficient and simple synthesis of ?-diketones, J. Mol. Catal. A: Chem., 176, 101-104.
38. Santos I. C. M. S., Rebelo S. L. H., Baluda M. S. S., Martins R. R. L., Pereira M. M. M. S., Simoes M. M. Q., Neves M. G. P. M. S., Cavaleiro J. A. S., Cavaleiro A. M. V. (2005) Association of Keggin-type anions with cationic meso-substituted porphyrins: synthesis, characterization and oxidative catalytic studies. J. Mol. Catal. A: Chem., 231, 35-45.
39. Giri N. G., Chauhan S. M. S. (2009) Oxidation of polycyclic aromatic hydrocarbons with hydrogen peroxide catalyzed by iron(III) porphyrins. Catal. Commun., 10, 383-387.
40. Rayati S., Zakavi S., Motalagh S. H., Noroozi, Razmjoo M., wojtczak A., Kozakiewicz A. (2008) B-Tetra-brominated meso-tetraphenylporphyrin V. A conformational study and application to the Mn-porphyrin catalyzed epoxidation of olefins with tetrabutylammoniumoxone. Polyhedron, 27, 2285-2290.
41. Adler A.D., Longo F. R., Finarelli J. D., Goldmacher J., Assour J., Korsakoff L. (1967) A simplified synthesis for meso-tetra phenylporphyrine. J. Org. Chem., 32, 476–476.
2. Wang Y., Deng K., Gui L., Tang Y., Zhou J.,Cai L., Qiu J., Ren D. (1999) Preparation and Characterization of Nanoscopic Organic Semiconductor of Oxovanadium Phthalocyanine. J. Colloid Interface. Sci., 213, 270-272.
3. Kasai H., Oikawa H., Okada S., Nakanishi H. (1998) Crystal Growth of Perylene Microcrystals in the Reprecipitation Method. Bull. Chem. Soc. Jpn. 71, 2597-2601.
4. Matsuda H., Yamada S., Keuren E. V., Katagi H., Kasai H., Okada S., Oikawa H., Nakanishi H., Smith E. C., Kar A. K., Wherrett B. S. (1997) Nonlinear refractive indexes of polydiacetylene microcrystals. Proc. SPIE., 2998, 241-248.
5. Tamaki Y., Asahi T., Masuharam H. (2000) Tailoring nanoparticles of aromatic and dye molecules by excimer laser irradiation. Appl. Surf. Sci., 168, 85-88.
6. Fu H. B., Yao J. N. (2001) Size Effects on the Optical Properties of Organic Nanoparticles. J. Am. Chem. Soc., 123, 1434-1439.
7. Fu H. B., Ji X. H., Yao J. N. (1999) The Size-dependent Property of 1,3,5-Triphenyl-2-pyrazoline Microcrystals. J. N. Chem. Lett., 9, 967-968.
8. Arun K. P., Prakriti R.B. (2008) Preparation and Characterization of free –standing pure porphyrin nanoparticles. J. Chem. Sci. 120, 485–491.
9. Zhong M. O., Hiroshi Y., Keisaku K. (2007) Preparation and optical properties of organic nanoparticles of porphyrin without self-aggregation. J. Photo. Chem. Photo. Bio. A: Chem., 189, 7-14.
10. Kashani-Motlagh M. M., Rahmatollah R., Javaheri-Kachousangi M. (2010) Ultrasonic method for the preparation of organic porphyrin nanoparticles, Molecules, 15, 280-287
11. Drain C. M., Nifiatis F., Vasenko A., Batteas J. D. (1998) Porphyrin tessellation by design: metal-mediated self-assembly of large arrays and tapes. Angew. Chem. Int. Ed. En., 37(17), 2344-2347.
12. Xu. W, Guo H., Akins D .L. (2001) Aggregation of Tetrakis(p-sulfonatophenyl) porphyrin within modified mesoporous MCM-41. J. Phys. Chem. B., 105, 1543-1546.
13. Akins D. L., Zhu H. R., Guo C. (1996) Aggregation of tetraaryl substitutedporphyrins in homogeneous solution. J. Phys. Chem., 100, 5420-5425.
14. Chou J. H., Kosal M. E., Nalwa H. S., Rakow N. A., Suslick K. S., Kadish K. M., Guilard R., Eds (2000) The porphyrin Handbook. Academic Press: New York, 6, 43-131.
15. Yoshiaki T., Tsuyoshi A., Hiroshi M. (2002) Nanoparticle formation of vanadyl phthalocyanine by laser ablation of its crystalline powder in a poor solvent. J. Phys. Chem. A, 106, 2135-2139.
16. Maiti N. C., Mazumdar S., Periasamy N. (1998) J- and H-Aggregates of porphyrin-surfactant complexes: time-resolved fluorescence and other spectroscopic studies. J. Phys. Chem. B, 102, 1528-1538.
17. Arun K. P., Prakriti R. B. (2008) Preparation and characterization of free–standing pure porphyrin nanoparticles. J. Chem. Sci., 120, 485-491.
18. Faulkner K. M., Liochev S. I., Fridovich I. (1994) Stable Mn(III) porphyrins mimic superoxide dismutase in vitro and substitute for it in vivo. J. Biol. Chem., 269 (38), 23471-23476
19. Xianchang G., Tatjana M., Chang X., James D. B. Charles M. D. (2002) Preparation and Characterization of Porphyrin Nanoparticles. J. Am. Chem. Soc., 124, 14290-14291.
20. Ghosh A., Selvamani T., Jose D. A., Das A., Mukhopadhyay I. (2007) Generation of nanostructures by the aggregation of porphyrin derivatives with long alkane chain in mix-solvent. J. Nanomater., Article ID 47234, doi:10.1155/2007/47234, 8 pages.
21. Debuigne F., Jeunieau L., Wiame M., Nagy J. B. (2000) Synthesis of Organic Nanoparticles in Different W/O Microemulsions. Langmuir, 16 (20), 7605-7611.
22. Tabushi I., Koga N. (1979) Synergetic combination of catalysis of the phase transfer-electron transfer type for the oxidation of alcohols or hydrocarbons. Tetrahedron Lett., 20, 3681-3684.
23. Labat G., Meunier B. (1989) Factors controlling the reactivity of a ligninase model based on the association of potassium monopersulfate to manganese and iron porphyrin complexes. J. Org. Chem., 54, 5008-5011.
24. Wietzerbin K., Meunier B., Bernadou J. (1997) Oxidation of tertiary diaryl alcohols catalyzed by a water-soluble metalloporphyrin: Caliph–Caliph versus Caliph–CAr bond cleavage. J. Chem. Commun., 23, 2321-2322.
25. Baciocchi E., Belvedere S. (1998) oxidation of ?-Alkylbenzyl Alcohols Catalysed by 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin Iron(III) Chloride Competition between C-H and C-C Bond Cleavage. Tetrahedron Lett., 39, 4711-4714.
26. Campestrini S., Cagnina A. (1999) A mechanistic study on oxidation of benzylic alcohols with PPh4HSO5catalysed by manganese_(III) porphyrins in homogeneous solution. J. Mol. Catal. A: Chem., 150, 77-86.
27. Moghadam M., Tangestaninejad S., Mirkhani V., Mohammadpoor-Baltork I. ,Kargar H. (2005) Mild and efficient oxidation of alcohols with sodium periodate catalyzed by polystyrene-bound Mn(III) porphyrin. Bioorg. Med. Chem., 13, 2901-2905.
28. Naik R., Joshi P., Deshpande R. K. (2005) Immobilization of metallporphyrins on polystyrene: Efficient catalysts for aerobic oxidation of alcohols. J. Mol. Catal. A: Chem., 238, 46-50.
29. Han J. H., Yoo S. K., Seo J. S., Hong S. J., Kim S. K., Kim C. (2005) Biomimetic alcohol oxidations by an iron(III) porphyrin complex: relevance to cytochrome P-450 catalytic oxidation and involvement of the two-state radical rebound mechanism. Dalton Trans., 2, 402-406.
30. Oh N. Y., Suh Y., Park M. J., Seo M. S., Kim J., Nam W. (2005) Mechanistic insight into alcohol oxidation by high-valent iron–oxo complexes of heme and nonheme ligands. Angew. Chem. Int. Ed., 44, 4235-4239.
31. Huang J. Y., Li S, J., Wang Y. G.(2006) TEMPO-linked metalloporphyrins as efficient catalysts for selective oxidation of alcohols and sulfides. Tetrahedron Lett., 47, 5637-5640.
32. Schults M. J., Sigman M. S. (2006) Recent advances in homogeneous transition metal-catalyzed aerobic alcohol oxidations. Tetrahedron, 62, 8227-8241.
33. Jiang N., Ragauskas A. J. (2007) Vanadium-catalyzed selective aerobic alcohol oxidation in ionic liquid [bmim]PF6 . Tetrahedron Lett., 48, 273-276.
34. Huang G., Luo J., Deng C. C., Guo Y. A., Zhao S. K.,Zhou H.,Wei S. (2008) Catalytic oxidation of toluene with molecular oxygen over manganese tetraphenylporphyrin supported on chitosan. Appl. Catal. A: Gen., 338, 83-86.
35. Yuan Y., Ji H., Chen Y., Han Y.,Song X., She Y., Zhong R. (2004) Oxidation of cyclohexane to adipic acid using fe-porphyrin as a biomimetic catalyst. Org. Process Res. Dev., 8, 418-420.
36. Zhou X. T., Ji H. B., Cheng Z., Xu J. C., Pei L. X., Wang L. F. (2007) Selective oxidation of sulfides to sulfoxides catalyzed by ruthenium(III) meso-tetraphenylporphyrin chloride in the presence of molecular oxygen. Bioorg. Med. Chem. Lett., 17, 4650-4653.
37. Jain S. L., sain B. (2001) Cobalt phthalocyanine tetrasulphonamide catalyzed aerobic oxidation of ?-hydroxyketones: an efficient and simple synthesis of ?-diketones, J. Mol. Catal. A: Chem., 176, 101-104.
38. Santos I. C. M. S., Rebelo S. L. H., Baluda M. S. S., Martins R. R. L., Pereira M. M. M. S., Simoes M. M. Q., Neves M. G. P. M. S., Cavaleiro J. A. S., Cavaleiro A. M. V. (2005) Association of Keggin-type anions with cationic meso-substituted porphyrins: synthesis, characterization and oxidative catalytic studies. J. Mol. Catal. A: Chem., 231, 35-45.
39. Giri N. G., Chauhan S. M. S. (2009) Oxidation of polycyclic aromatic hydrocarbons with hydrogen peroxide catalyzed by iron(III) porphyrins. Catal. Commun., 10, 383-387.
40. Rayati S., Zakavi S., Motalagh S. H., Noroozi, Razmjoo M., wojtczak A., Kozakiewicz A. (2008) B-Tetra-brominated meso-tetraphenylporphyrin V. A conformational study and application to the Mn-porphyrin catalyzed epoxidation of olefins with tetrabutylammoniumoxone. Polyhedron, 27, 2285-2290.
41. Adler A.D., Longo F. R., Finarelli J. D., Goldmacher J., Assour J., Korsakoff L. (1967) A simplified synthesis for meso-tetra phenylporphyrine. J. Org. Chem., 32, 476–476.