Browse > Article
http://dx.doi.org/10.5012/bkcs.2012.33.9.2937

Theoretical Analysis on Molecular Magnetic Properties of N-Confused Porphyrins and Its Derivatives  

Wei, Wei (State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University)
Bai, Fu-Quan (State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University)
Xia, Bao-Hui (State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University)
Zhang, Hong-Xing (State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.9, 2012 , pp. 2937-2942 More about this Journal
Abstract
We have theoretically investigated the magnetic properties of N-confused porphyrin (NCP), tetraphenyl-N-confused porphyrin (TPNCP) and their substituted derivatives with O, S and Se heteroatoms (2ONCP, 2STPNCP, 2SeNCP, 2OTPNCP, etc.) by using DFT method. In the minimum energy structures of the 2OTPNCP, the two couples opposite phenyl substitutes are staggered. In the case of TPNCP, 2STPNCP and 2SeTPNCP, two phenyls being respectively close to or opposite to N-confused pyrrole are found to be pointed the same direction, whilst others are in the opposite direction. Based on the equilibrium structures, the $^1H$ chemical shifts and nucleus-independent chemical shifts (NICS) are calculated in this paper. The ${\pi}$ current density being induced by the tridimensional perpendicular magnetic field transmits the inner section of the pyrrole segments for NCP and TPNCP. As for their substituted derivatives with O, S and Se atoms, the current path passes through the outer section of the two heterorings. The NICS values at the ring critical points of the heterorings are much lower (in absolute value) than those of which is at the center of an isolated pyrrole molecule. The $^1H$ NMR for ${\beta}H$ atoms of the heterorings decreases from O, S to with Se.
Keywords
Heteroporphyins; Hetero-N-confused porphyrins; NICS; ${\pi}$ current density; $^1H$ NMR;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
1 Harvey, J. D.; Ziegler, C. J. J. Inorg. Biochem. 2006, 100, 869.   DOI
2 Furuta, H.; Ishizuka, T.; Osuka, A.; Dejima, H.; Nakagawa, H.; Ishikawa, Y. J. Am. Chem. Soc. 2001, 123, 6207.   DOI
3 Yang, Z. D.; Feng, J. K.; Ren, A. M.; Sun, C. C. J. Phys. Chem. A 2006, 110, 13956.   DOI
4 Cardenas-Jirón, G. I.; Venegas, C.; Lopez, R.; Menendez, M. I. J. Phys. Chem. A 2008, 112, 8100.   DOI
5 Pushpan, S. K.; Chandrashekar, T. Pure Appl. Chem. 2002, 74, 2045.   DOI
6 Gupta, I.; Ravikanth, M. Coord. Chem. Rev. 2006, 250, 468.   DOI
7 Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.   DOI
8 Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.   DOI
9 Becke, A. D. Phys. Rev. A 1988, 38, 3098.   DOI
10 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.   DOI
11 Becke, A. D. J.Chem. Phys. 1993, 98, 5648.   DOI   ScienceOn
12 Frisch, M. J. et al. Gaussian 09, Revision A.02, Gaussian Inc.: Wallingford, CT, 2009.
13 Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.   DOI
14 Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
15 Bader, R. F. W.; Popelier, P. L. A.; Keith, T. A. Angew. Chem. Int. Ed. Engl. 1994, 33, 620.   DOI
16 Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.   DOI
17 Cyranski, M. K.; Krygowski, T. M.; Wisiorowski, M.; van Eikema, N. J. R.; Schleyer, P. V. R. Angew. Chem. Int. Ed. 1998, 37, 177.   DOI
18 Campomanes, P.; Menéndez, M. I.; Cárdenas-Jirón, G. I.; Sordo, T. L. Phys. Chem. Chem. Phys. 2007, 9, 5644.   DOI   ScienceOn
19 Maeda, H.; Osuka, A.; Furuta, H. J. Inclusion Phenom. Macrocycl. Chem. 2004, 49, 33.   DOI
20 Steiner, E.; Fowler, P. W. Chem. Phys. Chem. 2002, 3, 114.   DOI
21 Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.   DOI
22 Chmielewski, P. J.; Latos-Gra y ski, L.; Rachlewicz, K.; G owiak, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 779.   DOI
23 Morimoto, H.; Taniguchi, S.; Osuka, A.; Furuta, H. Eur. J. Org. Chem. 2005, 3887.
24 Lash, T.D. Synlett 1999, 3, 279
25 Latos-Gra y ski, L. In Core Modified Heteroanalogues of Porphyrins and Metalloporphyrins; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; The Porphyrin Handbook; Academic Press: San Diego, 2000.
26 Furuta, H.; Maeda, H.; Osuka, A. Chem. Commun. 2002, 1795.
27 Harvey, J. D.; Ziegler, C. J. Coord. Chem. Rev. 2003, 247, 1.   DOI
28 Maeda, H.; Furuta, H. J. Porphyrins Phthalocyanines 2004, 8, 67.   DOI
29 Srinivasan, A.; Furuta, H. Acc. Chem. Res. 2005, 38, 10.   DOI
30 Chmielewski, P. J.; Latos-Gra y ski, L. Coord. Chem. Rev. 2005, 249, 2510.   DOI
31 Ishizuka, T.; Furuta, H. J. Organosynth. Chem. 2005, 63, 211.
32 Maeda, H.; Furuta, H. Pure Appl. Chem. 2006, 78, 29.   DOI
33 Yoon, M. C.; Misra, R.; Yoon, Z. S.; Kim, K. S.; Lim, J. M.; Chandrashekar, T. K.; Kim, D. J. Phys. Chem. B 2008, 112, 6900.   DOI
34 Toganoh, M.; Furuta, H. J. Phys. Chem. A 2009, 113, 13953.   DOI   ScienceOn
35 Yan, L. K.; Pomogaeva, A.; Gu, F. L.; Aoki, Y. Theor. Chem. Acc. 2010, 125, 511.   DOI
36 Shin, J. Y.; Lim, J. M.; Yoon, Z. K.; Kim, K. S.; Yoon, M. C.; Hiroto, S.; Shinokubo, H.; Shimizu, S.; Osuka, A.; Kim, D. J. Phys. Chem. B 2009, 113, 5794.   DOI
37 Yu, M.; Zhang, W. Y.; Fan, Y.; Jian, W. P.; Liu, G. F. J. Phys. Org. Chem. 2007, 20, 229.   DOI   ScienceOn
38 Hu, H. Z.; Ma, S. Y. Int. J. Quantum Chem. 2010, 110, 1682.
39 Grochowski, P. Theor. Chem. Acc. 2008, 121, 257.   DOI
40 Pandey, R. K.; Sandeep, C. S. S.; Philip, R.; Lakshminarayanan, V. J. Phys. Chem. C 2009, 113, 8630.   DOI
41 Kuimova, M. K.; Yahioglu, G.; Ogilby, P. R. J. Am. Chem. Soc. 2009, 131(1), 332.   DOI
42 Lindsey, J. S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000.
43 Blau, W.; Byrne, H.; Dennis, W. M.; Kelly, J. M. Opt. Commun. 1985, 56, 25.   DOI
44 Wood, G. L.; Miller, M. J.; Mott, A. G. Opt. Lett. 1995, 20, 973.   DOI
45 Chen, P.; Tomov, I. V.; Dvornikov, A. S.; Nakashima, M.; Roach, J. F.; Alabran, D. M.; Rentzepis, P. M. J. Phys. Chem. 1996, 100, 17507.   DOI
46 Stiel, H.; Volkmer, A.; Rückmann, I.; Zeug, A.; Ehrenberg, B.; Röder, B. Opt. Commun. 1998, 155, 135.   DOI
47 Castevens, C. M. Theor. Chem. Acc. 2008, 121, 43.   DOI
48 Lloyd, D. J. Chem. Inf. Comput. Sci. 1996, 36, 442.   DOI
49 Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; John Wiley & Sons: New York, 1994.
50 Schleyer, P. v. R.; Jiao, H. Pure. Appl. Chem. 1996, 68, 209.   DOI
51 Krygowski, T. M.; Crya ski, M. K.; Czarnocki, Z.; Häfelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783.   DOI
52 Schleyer, P. v. R. Chem. Rev. 2001, 101, 1115.   DOI
53 Faraday, M. Philos. Trans. R. Soc. 1825, 115, 440.   DOI
54 Garratt, P. J. Aromaticity; Wiley: New York, 1986
55 Jerry, M. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd ed.; Wiley: New York, 1985.
56 Heilbronner, E. Tetrahedron Lett. 1964, 5, 1923.   DOI
57 Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.   DOI
58 Turker, L.; Gumu , S.; Atalar, T. Bull. Korean Chem. Soc. 2009, 30, 2333.
59 Jeon, K. O.; Jun, J. H.; Yu, J. S.; Lee, C. K. Bull. Korean Chem. Soc. 2004, 25, 1840.   DOI
60 Hong, S. Y.; Kim, S. C. Bull. Korean Chem. Soc. 2003, 24, 1649.   DOI
61 Schleyer, P. v. R.; Jiao, H. J.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669.   DOI
62 Chen, Z. F.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842.   DOI
63 Shin, J. Y.; Kim, K. S.; Yoon, M. C.; Lim, J. M.; Yoon, Z. S.; Osuka, A.; Kim, D. Chem. Soc. Rev. 2010, 39, 2751.   DOI