Spectroscopy of protonated tetraphenylporphyrins with amino/carbomethoxy substituents: Hyperporphyrin effects and evidence for a monoprotonated porphyrin

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6040-6049

  Rudine, Alexander B ^a   Delfatti, Brian D ^a   Wamser, Carl C ^a  

^a PORTLAND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE DELOCALIZATION; ELECTRONWITHDRAWING; METHANE SULFONIC ACID; RELATIVE BASICITY; RELATIVE STABILITIES; SPECTROPHOTOMETRIC TITRATIONS; SUBSTITUTION PATTERNS; TETRAPHENYLPORPHYRINS;

PORPHYRINS; TITRATION;

PROTONATION;

DIMETHYL SULFOXIDE; MESYLIC ACID; PORPHYRIN; TETRAPHENYLPORPHYRIN DERIVATIVE;

ARTICLE; ISOMER; PROTON TRANSPORT; SPECTROPHOTOMETRY; SUBSTITUTION REACTION; TITRIMETRY;

DIMETHYL SULFOXIDE; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; PORPHYRINS; PROTONS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 84879342129     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400742f     Document Type: Article

References (46)

1. Sharman, W. M.; van Lier, J. E.; Allen, C. M. Adv. Drug Delivery Rev. 2004, 56, 53
2. Kalyani, N. T.; Dhoble, S. J. Renew. Sust. Energy Rev. 2012, 16, 2696
3. Walter, M. G.; Rudine, A. B.; Wamser, C. C. J. Porphyrins Phthalocyanines 2010, 14, 759
4. Imahori, H.; Kurotobi, K.; Walter, M. G.; Rudine, A. B.; Wamser, C. C. In Handbook of Porphyrin Science; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific: Singapore, 2012; Vol. 18, p 58.
5. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3, p 1.
6. Sayer, P.; Gouterman, M.; Connell, C. R. Acc. Chem. Res. 1982, 15, 73
7. Goldberg, P. K.; Pundsack, T. J.; Splan, K. E. J. Phys. Chem. A 2011, 115, 10452
8. Ojadi, E. C. A.; Linschitz, H.; Gouterman, M.; Walter, R. I.; Lindsey, J. S.; Wagner, R. W.; Droupadi, P. R.; Wang, W. J. Phys. Chem. 1993, 97, 13192
9. Walter, R. I.; Ojadi, E. C. A.; Linschitz, H. J. Phys. Chem. 1993, 97, 13308
10. Wasbotten, I. H.; Conradie, J.; Ghosh, A. J. Phys. Chem. B 2003, 107, 3613
11. Weinkauf, J. R.; Cooper, S. W.; Schweiger, A.; Wamser, C. C. J. Phys. Chem. A 2002, 107, 3486
12. De Luca, G.; Romeo, A.; Scolaro, L. M. J. Phys. Chem. B 2006, 110, 14135
13. Guo, H.; Jiang, J.; Shi, Y.; Wang, Y.; Dong, S. Spectrochim. Acta, Part A 2007, 67, 166
14. Guo, H.; Jiang, J.; Shi, Y.; Wang, Y.; Liu, J.; Dong, S. J. Phys. Chem. B 2004, 108, 10185
15. Guo, H.; Jiang, J.; Shi, Y.; Wang, Y.; Wang, Y.; Dong, S. J. Phys. Chem. B 2006, 110, 587
16. Walter, M. G.; Wamser, C. C. J. Phys. Chem. C. 2010, 114, 7563
17. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 71
18. Aronoff, S. J. Phys. Chem. 1958, 62, 428
19. Austin, E.; Gouterman, M. Bioinorg. Chem. 1978, 9, 281
20. Chauvin, B.; Kasselouri, A.; Chaminade, P.; Quiameso, R.; Nicolis, I.; Maillard, P.; Prognon, P. Anal. Chim. Acta 2011, 705, 306
21. Cheng, B.; Munro, O. Q.; Marques, H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732
22. Corwin, A. H.; Chivvis, A. B.; Poor, R. W.; Whitten, D. G.; Baker, E. W. J. Am. Chem. Soc. 1968, 90, 6577
23. De Luca, G.; Romeo, A.; Scolaro, L. M. J. Phys. Chem. B 2005, 109, 7149
24. De Luca, G.; Romeo, A.; Scolaro, L. M. J. Phys. Chem. B 2006, 110, 7309
25. Fleischer, E. B.; Webb, L. E. J. Phys. Chem. 1963, 67, 1131
26. Freeman, K. A.; Hibbert, F.; Hunte, K. P. P. J. Chem. Soc., Perkin Trans. 2 1979, 1237
27. Hambright, P.; Fleisher, E. B. Inorg. Chem. 1970, 9, 1757
28. Hibbert, F.; Hunte, K. P. P. J. Chem. Soc., Perkin Trans. 2 1977, 1624
29. Karaman, R.; Bruice, T. C. Inorg. Chem. 1992, 31, 2455
30. Pasternack, R. F.; Sutin, N.; Turner, D. H. J. Am. Chem. Soc. 1976, 98, 1908
31. Rau, W. G.; Longo, F. R. Inorg. Chem. 1977, 16, 1372
32. Stone, A.; Fleischer, E. B. J. Am. Chem. Soc. 1968, 90, 2735
33. Walter, R. I. J. Am. Chem. Soc. 1953, 75, 3860
34. Honda, T.; Kojima, T.; Fukuzumi, S. Chem. Commun. 2009, 4994
35. De Luca, G.; Romeo, A.; Scolaro, L. M.; Ricciardi, G.; Rosa, A. Inorg. Chem. 2007, 46, 5979
36. Thyagarajan, S.; Leiding, T.; Årsköld, S. P.; Cheprakov, A. V.; Vinogradov, S. A. Inorg. Chem. 2010, 49, 9909
37. Almarsson, O.; Blasko, A.; Bruice, T. C. Tetrahedron 1993, 49, 10239
38. Hirayama, N.; Takenaka, A.; Sasada, Y.; Watanabe, E.-I.; Ogoshi, H.; Yoshida, Z.-I. J. Chem. Soc., Chem. Commun. 1974, 330
39. Gunter, M. J.; Robinson, B. C. Aust. J. Chem. 1989, 42, 1897
40. Hatay, I.; Su, B.; Méndez, M. A.; Corminboeuf, C.; Khoury, T.; Gros, C. P.; Bourdillon, M.; Meyer, M.; Barbe, J.-M.; Ersoz, M.; Záliš, S.; Samec, Z.; Girault, H. H. J. Am. Chem. Soc. 2010, 132, 13733
41. Chirvony, V. S.; van Hoek, A.; Galievsky, V. A.; Sazanovich, I. V.; Schaafsma, T. J.; Holten, D. J. Phys. Chem. B 2000, 104, 9909
42. Vitasovic, M.; Gouterman, M.; Linschitz, H. J. Porphyrins Phthalocyanines 2001, 5, 191
43. Ransdell, R. A.; Wamser, C. C. J. Phys. Chem. 1992, 96, 10572
44. Gouterman, M.; Wagniere, G. H.; Snyder, L. C. J. Mol. Spectrosc. 1963, 11, 108
45. Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476
46. Walter, M. G.; Wamser, C. C.; Ruwitch, J.; Zhao, Y.; Braden, D.; Stevens, M.; Denman, A.; Pi, R.; Rudine, A.; Pessiki, P. J. J. Porphyrins Phthalocyanines 2007, 11, 601