Solvent-dependent deprotonation of meso -pyrimidinylcorroles: Absorption and fluorescence studies

Journal of Physical Chemistry A

Volumn 116, Issue 44, 2012, Pages 10704-10711

  Kruk, Mikalai ^a   Ngo, Thien H ^b,c   Savva, Vadim ^a   Starukhin, Aleksander ^a   Dehaen, Wim ^b   Maes, Wouter ^b,d  

^a B I STEPANOV INSTITUTE OF PHYSICS   (Belarus)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d HASSELT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CORROLES; DEPROTONATED SPECIES; FLUORESCENCE PROPERTIES; FLUORESCENCE STUDIES; INTRAMOLECULAR HYDROGEN BONDING; MACROCYCLES; MULTIPARAMETERS; PREFERENTIAL SOLVATION; PROTONATED SPECIES; SINGLE SOLVENTS; SOLUTE-SOLVENT INTERACTION; SOLVENT PROPERTIES;

ELECTROMAGNETIC WAVE ABSORPTION; FLUORESCENCE; HYDROGEN BONDS; POLYPYRROLES;

SOLVENTS;

10 (4,6 DICHLOROPYRIMIDIN 5 YL) 5,15 DIMESITYLCORROLE; 10-(4,6-DICHLOROPYRIMIDIN-5-YL)-5,15-DIMESITYLCORROLE; PORPHYRIN; PROTON; SOLVENT;

ARTICLE; CHEMISTRY; FLUORESCENCE; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

FLUORESCENCE; PORPHYRINS; PROTONS; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84868554812     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp305327c     Document Type: Article

References (50)

1. Aviv, I.; Gross, Z. Chem. Commun. 2007, 1987-1999
2. Flamigni, L.; Gryko, D. T. Chem. Soc. Rev. 2009, 38, 1635-1646
3. Aviv-Harel, I.; Gross, Z. Chem.-Eur. J. 2009, 15, 8382-8394
4. Aviv-Harel, I.; Gross, Z. Coord. Chem. Rev. 2011, 255, 717-736
5. Barbe, J.-M.; Canard, G.; Brandès, S.; Guilard, R. Chem.-Eur. J. 2007, 13, 2118-2129
6. Mahammed, A.; Gross, Z. Chem. Commun. 2010, 7040-7042
7. Kupershmidt, L.; Okun, Z.; Amit, T.; Mandel, S.; Saltsman, I.; Mahammed, A.; Bar-Am, O.; Gross, Z.; Youdim, M. B. H. J. Neurochem. 2010, 113, 363-373
8. Abu-Omar, M. M. Dalton Trans. 2011, 40, 3435-3444
9. Suranjana Bose, S.; Pariyar, A.; Biswas, A. N.; Das, P.; Bandyopadhyay, P. Catal. Commun. 2011, 12, 446-449
10. Dogutan, D. K.; McGuire, R.; Nocera, D. G. J. Am. Chem. Soc. 2011, 133, 9178-9180
11. Aviv-Harel, I.; Gross, Z. Coord. Chem. Rev. 2011, 255, 717-736
12. Flamigni, L.; Ciuciu, A. I.; Langhals, H.; Böck, B.; Gryko, D. T. Chem. Asian J. 2012, 7, 582-592
13. Johnson, A. W.; Kay, I. T. J. Chem. Soc. 1965, 1620-1629
14. Gryko, D. T. Eur. J. Org. Chem. 2002, 1735-1743
15. Gryko, D. T.; Fox, J. P.; Goldberg, P. J. Porphyrins Phthalocyanines 2004, 8, 1091-1105
16. Ghosh, A. Angew. Chem., Int. Ed. 2004, 43, 1918-1931
17. Nardis, S.; Monti, D.; Paolesse, R. Mini-Rev. Org. Chem. 2005, 2, 355-374
18. Paolesse, R. Synlett 2008, 2215-2230
19. Gryko, D. T. J. Porphyrins Phthalocyanines 2008, 12, 906-917
20. Lemon, C. M.; Brothers, P. J. J. Porphyrins Phthalocyanines 2011, 15, 809-834
21. Ding, T.; Aleman, E. A.; Modarelli, D. A.; Ziegler, C. J. J. Phys. Chem. A 2005, 109, 7411-7417
22. Mahammed, A.; Weaver, J. J.; Gray, H. B.; Abdelas, M.; Gross, Z. Tetrahedron Lett. 2003, 44, 2077-2079
23. Ivanova, Y. B.; Savva, V. A.; Mamardashvili, N. Z.; Starukhin, A. S.; Ngo, T. H.; Dehaen, W.; Maes, W.; Kruk, M. M. J. Phys. Chem. A. 2012, companion article 10.1021/jp305325e
24. Gross, Z.; Galili, N.; Saltsman, I. Angew. Chem., Int. Ed. 1999, 38, 1427-1429
25. Paolesse, R.; Jaquinod, L.; Nurco, D. J.; Mini, S.; Sagone, F.; Boschi, T.; Smith, K. M. Chem. Commun. 1999, 1307-1308
26. Simkovich, L.; Goldberg, I.; Gross, Z. J. Inorg. Biochem. 2000, 80, 235-238
27. Bendix, J.; Dmochowski, I. J.; Gray, H. B.; Mahammed, A.; Simkovich, L.; Gross, Z. Angew. Chem., Int. Ed. 2000, 39, 4048-4051
28. Shen, J.; Shao, J.; Ou, Z.; E, W.; Koszarna, B.; Gryko, D. T.; Kadish, K. M. Inorg. Chem. 2006, 45, 2251-2265
29. Shen, J.; Ou, Z.; Shao, J.; Galezowski, M.; Gryko, D. T.; Kadish, K. M. J. Porphyrins Phthalocyanines 2007, 11, 269-276
30. Ou, Z.; Sun, H.; Zhu, W.; Da, Z; Kadish, K. M. J. Porphyrins Phthalocyanines 2008, 12, 1-10
31. Maes, W.; Ngo, T. H.; Vanderhaeghen, J.; Dehaen, W. Org. Lett. 2007, 9, 3165-3168
32. Ngo, T. H.; Van Rossom, W.; Dehaen, W.; Maes, W. Org. Biomol. Chem. 2009, 7, 439-443
33. Ngo, T. H.; Puntoriero, F.; Nastasi, F.; Robeyns, K.; Van Meervelt, L.; Campagna, S.; Dehaen, W.; Maes, W. Chem.-Eur. J. 2010, 16, 5691-5705
34. Ngo, T. H.; Nastasi, F.; Puntoriero, F.; Campagna, S.; Dehaen, W.; Maes, W. J. Org. Chem. 2010, 75, 2127-2130
35. Nastasi, F.; Campagna, S.; Ngo, T. H.; Dehaen, W.; Maes, W.; Kruk, M. Photochem. Photobiol. Sci. 2011, 10, 143-150
36. Ngo, T. H.; Nastasi, F.; Puntoriero, F.; Campagna, S.; Dehaen, W.; Maes, W. Eur. J. Org. Chem. 2012, 28, 5605-5617
37. Knyukshto, V.; Zenkevich, E.; Sagun, E.; Shulga, A.; Bachilo, S. Chem. Phys. Lett. 1998, 297, 97-108
38. Ou, Z.; Shen, J.; Shao, J.; E, W.; Galezowski, M.; Gryko, D. T.; Kadish, K. M. Inorg. Chem. 2007, 46, 2775-2786
39. Laurence, C.; Graton, J.; Berthelot, M.; Besseau, F.; Le Questel, J.-Y.; Luçon, M.; Ouvrard, C.; Planchat, A.; Renault, E. J. Org. Chem. 2010, 75, 4105-4123
40. Gutmann, V. Electrochim. Acta 1976, 21, 661-670
41. Swain, C. G.; Swain, M. S.; Powell, A. L.; Alunni, S. J. Am. Chem. Soc. 1983, 105, 502-513
42. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383
43. Krygowski, T. M.; Milczarek, E.; Wrona, P. K. J. Chem. Soc., Perkin Trans. 2 1980, 1563-1568
44. Reichardt, C.; Welton, T. Solvents and Solvent Effects in Organic Chemistry, 4 th ed.; Wiley-VCH: Weinheim, Germany, 2010.
45. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358
46. Fawcett, W. R. J. Phys. Chem. 1993, 97, 9540-9546
47. Balazs, Y. S.; Saltsman, I.; Mahammed, A.; Tkachenko, E.; Golubkov, G.; Levine, J.; Gross, Z. Magn. Reson. Chem. 2004, 42, 624-635
48. Ghosh, A.; Jynge, K. Chem.-Eur. J. 1997, 3, 823-833
49. Ghosh, A. Acc. Chem. Res. 1998, 31, 189-198
50. Kruk, M. M.; Ngo, T. H.; Verstappen, P.; Starukhin, A. S.; Hofkens, J.; Dehaen, W.; Maes, W. J. Phys. Chem. A. 2012, companion article 10.1021/jp305326x