Free base and metal complexes of 5,15-diaza-10,20-dimesitylporphyrins: Synthesis, structures, optical and electrochemical properties, and aromaticities

Inorganic Chemistry

Volumn 51, Issue 23, 2012, Pages 12879-12890

  Matano, Yoshihiro ^a   Shibano, Tarou ^a   Nakano, Haruyuki ^b   Kimura, Yoshifumi ^c   Imahori, Hiroshi ^a,d  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c HOSEI UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; PALLADIUM; PLATINUM; PORPHYRIN; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; LIGHT RELATED PHENOMENA; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMICAL TECHNIQUES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OPTICAL PROCESSES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PLATINUM; PORPHYRINS; STEREOISOMERISM; ZINC;

EID: 84870483192     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic301835c     Document Type: Article

References (59)

1. Fischer, H.; Harberland, H.; Müller, A. Justus Liebigs Ann. Chem 1936, 521, 122-128
2. Kobayashi, N. In The Porphyrin Handbook; Kadish, K. M.; Smith, R. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 301-360.
3. Ogata, H.; Fukuda, T.; Nakai, K.; Fujimura, Y.; Neya, S.; Stuzhin, P. A.; Kobayashi, N. Eur. J. Inorg. Chem. 2004, 1621-1629
4. Stuzhin and Khelevina summarized the metal complex formation of diazaporphyrins, see: Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41-86
5. Kaczmarzyk, T.; Jackowski, T.; Dzilinski, K.; Kania, L. Acta Phys. Pol., A 2009, 115, 656-659
6. Stuzhin, P. A.; Nefedov, S. E.; Kumeev, R. S.; Ul-Haq, A.; Minin, V. V.; Ivanova, S. S. Inorg. Chem. 2010, 49, 4802-4813
7. Stuzhin, P. A.; Ul-Haq, A.; Nefedov, S. E.; Kumeev, R. S.; Koifman, O. I. Eur. J. Inorg. Chem. 2011, 2567-2578
8. Neya, S.; Hori, H.; Imai, K.; Kawamura-Konishi, Y.; Suzuki, H.; Shiro, Y.; Iizuka, T.; Funasaki, N. J. Biochem. 1997, 121, 654-660
9. Ohgo, Y.; Neya, S.; Uekusa, H.; Nakamura, M. Chem. Commun. 2006, 4590-4592 (Correction: 2008, 6609)
10. Shinmori, H.; Kodaira, F.; Matsugo, S.; Kawabata, S.; Osuka, A. Chem. Lett. 2005, 34, 322-323
11. Optical oxygen-sensing with palladium and platinum complexes of 5,10-diazaporphyrin was also reported. Borisov, S. M.; Zenkl, G.; Klimant, I. ACS Appl. Mater. Interfaces 2010, 2, 366-374
12. Okujima, T.; Jin, G.; Otsubo, S.; Aramaki, S.; Ono, N.; Yamada, H.; Uno, H. J. Porphyrins Phthalocyanines 2011, 15, 697-703
13. Pan, N.; Bian, Y.; Fukuda, T.; Yokoyama, M.; Li, R.; Neya, S.; Jiang, J.; Kobayashi, N. Inorg. Chem. 2004, 43, 8242-8244
14. Pan, N.; Bian, Y.; Yokoyama, M.; Li, R.; Fukuda, T.; Neya, S.; Jiang, J.; Kobayashi, N. Eur. J. Inorg. Chem. 2008, 5519-5523
15. Chizhova, N. V.; Toldina, O. V.; Mamardashvili, N. Z. Russ. J. Inorg. Chem. (Engl. Transl.) 2008, 53, 1401-1404
16. Harris, R. L. N.; Johnson, A. W.; Kay, I. T. J. Chem. Soc. (C) 1966, 22-29
17. Galanin, N. E.; Kudrik, E. V.; Shaposhnikov, G. P. Russ. J. Gen. Chem. 2005, 75, 651-655
18. Galanin, N. E.; Yakubov, L. A.; Kudrik, E. V.; Shaposhnikov, G. P. Russ. J. Gen. Chem. 2008, 78, 1436-1440
19. Bykova, V.; Usol'tseva, N.; Kudrik, E.; Galanin, N.; Shaposhnikov, G.; Yakubov, L. Mol. Cryst. Liq. Cryst. 2008, 494, 38-47
20. Two β -unsubstituted DAP-copper complexes were reported in a patent, although the yields and the spectral data are not described. Ogiso, A.; Inoue, S.; Nishimoto, T.; Tsukahara, H.; Misawa, T.; Koike, T.; Mihara, N.; Murayama, S.; Nara, R. WO-A1-2001047719, 2001.
21. Matano, Y.; Shibano, T.; Nakano, H.; Imahori, H. Chem.-Eur. J. 2012, 18, 6208-6216
22. Shinokubo and coworkers independently reported the formation of 2Ni in their original synthesis of azacorroles. See: Horie, M.; Hayashi, Y.; Yamaguchi, S.; Shinokubo, H. Chem.-Eur. J. 2012, 18, 5919-5923
23. Maeda, H.; Hashimoto, T.; Fujii, R.; Hasegawa, M. J. Nanosci. Nanotechnol. 2009, 9, 240-248
24. 2 in DMF. See: Khelevina, O. G.; Chizhova, N. V.; Stuzhin, P. A.; Semeikin, A. S.; Berezin, B. D. Russ. J. Phys. Chem. (Engl. Transl.) 1997, 71, 74-78
25. Emsley, J. The Elements, 3 rd ed.; Oxford University Press: New York, 1998. Covalent bond radii and electronegativities (Pauling): 1.54 Å and 2.33 for Pb; 1.15 Å and 1.91 for Ni; 1.28 Å and 2.20 for Pd; and 1.29 Å and 2.28 for Pt; 1.25 Å and 1.65 for Zn; 1.50 Å and 1.78 for In.
26. Stuzhin, P. A.; Goeldner, M.; Homborg, H.; Semeikin, A. S.; Migalova, I. S.; Wolowiec, S. Mendeleev Commun. (Engl. Transl.) 1999, 9, 134-136
27. Khelevina, O. G.; Stuzhin, P. A.; Migalova, I. S.; Shukhto, O. V. Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71, 1647-1652
28. Stuzhin, P. A.; Ivanova, S. S.; Migalova, I. S. Russ. J. Gen. Chem. (Engl. Transl.) 2004, 74, 1435-1445
29. Yu, L.; Muthukumaran, K.; Sazanovich, I. V.; Kirmaier, C.; Hindin, E.; Diers, J. R.; Boyle, P. D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Inorg. Chem. 2003, 42, 6629-6647
30. 6 as an electrolyte)
31. Dolphin, D.; Niem, T.; Felton, R. H.; Fujita, I. J. Am. Chem. Soc. 1975, 97, 5288-5290
32. Johnson, E. C.; Niem, T.; Dolphin, D. Can. J. Chem. 1978, 56, 1381-1388
33. Chang, D.; Malinski, T.; Ulman, A.; Kadish, K. M. Inorg. Chem. 1984, 23, 817-824
34. Ou, Z.; Cheng, P.; Kadish, K. M. Dalton Trans. 2010, 39, 11272-11276
35. Cheng, P.; Finikova, O. S.; Ou, Z.; Vinogradov, S. A.; Kadish, K. M. Inorg. Chem. 2012, 51, 6200-6210
36. Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 3839-3842
37. Krygowski, T. M. J. Chem. Inf. Comput. Sci. 1993, 33, 70-78
38. Krygowski, T. M.; Ciesielski, A.; Bird, C. W.; Kotschy, A. J. Chem. Inf. Comput. Sci. 1995, 35, 203-210
39. Cyrañski, M. K.; Krygowski, T. M.; Wisiorowski, M.; van Eikema Hommes, N. J. R.; Schleyer, P.; von, R. Angew. Chem., Int. Ed. 1998, 37, 177-180
40. For example, see: Matano, Y.; Matsumoto, K.; Hayashi, H.; Nakao, Y.; Kumpulainen, T.; Chukharev, V.; Tkachenko, N. V.; Lemmetyinen, H.; Shimizu, S.; Kobayashi, N.; Sakamaki, D.; Ito, A.; Tanaka, K.; Imahori, H. J. Am. Chem. Soc. 2012, 134, 1825-1839
41. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13
42. Bajema, L.; Gouterman, M.; Rose, C. B. J. Mol. Spectrosc. 1971, 39, 421-431
43. Hasegawa, J.; Kimura, T.; Nakatsuji, H. J. Porphyrins Phthalocyanines 2005, 9, 305-315. SAC-CI: Symmetry Adapted Cluster Configuration Interaction
44. SIR92 (for 1Zn, 4Ni): Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435-436
45. 2, 2Pd, 2Pt): Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Crystallogr. 2007, 40, 609-613.
46. SHELXL-97: Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
47. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
48. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033-1036
49. Hay, P. J. J. Chem. Phys. 1977, 66, 4377-4384
50. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062-1065
51. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
52. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
53. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317-6318
54. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261
55. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222
56. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P.; von, R. J. Comput. Chem. 1983, 4, 294-301
57. Rassolov, V.; Pople, J. A.; Ratner, M.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223-1229
58. Cancès, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041
59. Frisch, M. J.; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2010. For a full list of authors, see the Supporting Information.