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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access January 23, 2013

Fullerenes patched by flowers

Raluca Pop, Mihai Medeleanu, Mircea Diudea, Beata Szefler and Jerzy Cioslowski
From the journal Open Chemistry

Abstract

Stability measures, such as the total energy and the HOMO-LUMO gap, calculated at the Hartree-Fock and DFT levels of theory, and the aromatic character of five circulenes/flowers with a hexagonal core and petals consisting of 5-, 6- and 7-membered rings are investigated. Geometric (HOMA) and magnetic (NICS) criteria are used to estimate the local aromatic character of every ring of the investigated circulenes. The local aromaticity of the coronene and sumanene patches in two tetrahedrally spanned fullerenes were calculated and compared with the HOMA and NICS values of the corresponding isolated circulenes.

[1] M.V. Diudea, Nanomolecules and Nanostructures — Polynomials and Indices (MCM, Univ. Kragujevac, Serbia, 2010) No. 10 Search in Google Scholar

[2] M.V. Diudea, Cs.L. Nagy, Periodic Nanostructures (Springer, Netherlands, 2007) http://dx.doi.org/10.1007/978-1-4020-6020-510.1007/978-1-4020-6020-5Search in Google Scholar

[3] M.V. Diudea (Ed.), Nanostructures, Novel Architecture (Nova, New York, 2005) Search in Google Scholar

[4] K.Yu. Amsharov, M. Jansen, J. Org. Chem. 73, 2931 (2008) http://dx.doi.org/10.1021/jo702700810.1021/jo7027008Search in Google Scholar

[5] K.Yu. Amsharov, M. Jansen, Chem. Commun. 2691 (2009) 10.1039/b901496aSearch in Google Scholar

[6] E. Barborini, P. Piseri, P. Milani, G. Benedek, C. Ducati, J. Robertson, Appl. Phys. Lett. 81, 3359 (2002) http://dx.doi.org/10.1063/1.151663510.1063/1.1516635Search in Google Scholar

[7] G. Benedek, H. Vahedi-Tafreshi, E. Barborini, P. Piseri, P. Milani, C. Ducati, J. Robertson, Diamond Relat. Mater. 12, 768 (2003) http://dx.doi.org/10.1016/S0925-9635(03)00082-710.1016/S0925-9635(03)00082-7Search in Google Scholar

[8] E. Clar, Polycyclic Hydrocarbons (Acad. Press, London, 1964) 10.1007/978-3-662-01668-8Search in Google Scholar

[9] E. Clar, The Aromatic Sextet (Wiley, New York, 1972) Search in Google Scholar

[10] P.W. Fowler, T. Pisanski, J. Chem. Soc., Faraday Trans. 90, 2865 (1994) http://dx.doi.org/10.1039/ft994900286510.1039/ft9949002865Search in Google Scholar

[11] J.R. Dias, Handbook of Polycyclic Hydrocarbons (Elsevier, Amsterdam, 1987) Part A Search in Google Scholar

[12] I. Gutman, S.J. Cyvin, Introduction to the Theory of Benzenoid Hydrocarbons (Springer, Berlin, 1989) http://dx.doi.org/10.1007/978-3-642-87143-610.1007/978-3-642-87143-6Search in Google Scholar

[13] M.V. Diudea, Phys. Chem., Chem. Phys. 7, 3626 (2005) http://dx.doi.org/10.1039/b510223e10.1039/b510223eSearch in Google Scholar PubMed

[14] M.V. Diudea, Forma (Tokyo) 19, 131 (2004) Search in Google Scholar

[15] M.V. Diudea, In: M.V. Diudea (Ed.), Nanostructures-Novel Architecture (Nova, New York, 2005) 203–242 Search in Google Scholar

[16] M.V. Diudea, In: M.V. Diudea (Ed.), Nanostructures-Novel Architecture (Nova, New York, 2005) 111–126 Search in Google Scholar

[17] M.V. Diudea, M. Ştefu, P.E. John, A. Graovac, Croat. Chem. Acta 79, 355 (2006) Search in Google Scholar

[18] M.V. Diudea, J. Chem. Inf. Model. 45, 1002 (2005) http://dx.doi.org/10.1021/ci050054y10.1021/ci050054ySearch in Google Scholar PubMed

[19] M.V. Diudea, A.E. Vizitiu, Cs.L. Nagy, T. Beu, A. Bende, D. Janežič, J. Mol. Struct. THEOCHEM 904, 28 (2009) http://dx.doi.org/10.1016/j.theochem.2009.02.02410.1016/j.theochem.2009.02.024Search in Google Scholar

[20] J.T. Craig, B. Halton, S. Lo, Austral. J. Chem. 28, 913 (1975) http://dx.doi.org/10.1071/CH975091310.1071/CH9750913Search in Google Scholar

[21] K. Yamamoto, Pure Appl. Chem. 65, 157 (1993) http://dx.doi.org/10.1351/pac19936501015710.1351/pac199365010157Search in Google Scholar

[22] H. Sakurai, T. Daiko, T. Hirao, Science 301, 1878 (2003) http://dx.doi.org/10.1126/science.108829010.1126/science.1088290Search in Google Scholar

[23] H. Sakurai, T. Daiko, H. Sakane, T. Amaya, T. Hirao, J. Am. Chem. Soc. 127, 11580 (2005) http://dx.doi.org/10.1021/ja051816910.1021/ja0518169Search in Google Scholar

[24] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.1, (Gaussian Inc., Wallingford CT, 2009) Search in Google Scholar

[25] P.v.R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. Van Eikema Hommes, J. Am. Chem. Soc. 118, 6317 (1995) http://dx.doi.org/10.1021/ja960582d10.1021/ja960582dSearch in Google Scholar

[26] D.B. Chesnut, K.D. Moore, J. Comput. Chem. 10, 648 (1985) http://dx.doi.org/10.1002/jcc.54010050710.1002/jcc.540100507Search in Google Scholar

[27] T.M. Krygowski, A. Ciesielski, J. Chem. Inf. Comput. Sci. 35, 203 (1995) http://dx.doi.org/10.1021/ci00024a00610.1021/ci00024a006Search in Google Scholar

[28] T.M. Krygowski, A. Ciesielski, J. Chem. Inf. Comput. Sci. 35, 1001 (1995) http://dx.doi.org/10.1021/ci00028a00610.1021/ci00028a006Search in Google Scholar

[29] T.M. Krygowski, M. Cyranski, Tetrahedron 52, 10255 (1996) http://dx.doi.org/10.1016/0040-4020(96)00560-110.1016/0040-4020(96)00560-1Search in Google Scholar

[30] C.L. Nagy, M.V. Diudea, JSChem software program („Babes-Bolyai“ Univ., Cluj, 2005) Search in Google Scholar

[31] M. Randić, Chem. Rev. 103, 3449 (2003) http://dx.doi.org/10.1021/cr990365610.1021/cr9903656Search in Google Scholar PubMed

[32] A. Ciesielski, M.K Cyrański, T.M Krygowski, P.W Fowler, M. Lillington, J. Org. Chem. 71, 6840 (2006) http://dx.doi.org/10.1021/jo060898w10.1021/jo060898wSearch in Google Scholar PubMed

[33] A. Ciesielski, T.M. Krygowski, M.K. Cyrański, A.T. Balaban, Phys. Chem. Chem. Phys. 13, 3737 (2011) http://dx.doi.org/10.1039/c0cp01446j10.1039/C0CP01446JSearch in Google Scholar PubMed

[34] R.C. Haddon, J. Am. Chem. Soc. 109, 1676 (1987) http://dx.doi.org/10.1021/ja00240a01310.1021/ja00240a013Search in Google Scholar

[35] R.C. Haddon, J. Phys. Chem. A 105, 4164 (2001) http://dx.doi.org/10.1021/jp010023f10.1021/jp010023fSearch in Google Scholar

[36] P.v.R. Schleyer, P.K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem. Int. Ed. Engl. 34, 337 (1995) http://dx.doi.org/10.1002/anie.19950337110.1002/anie.199503371Search in Google Scholar

[37] N.S. Mills, M. Benish, J. Org. Chem. 21, 2207 (2006) http://dx.doi.org/10.1021/jo051621j10.1021/jo051621jSearch in Google Scholar PubMed

[38] T.K. Zywietz, H. Jiao, P.v.R. Schleyer, A. de Meijere, J. Org. Chem. 63, 3417 (1998) http://dx.doi.org/10.1021/jo980089f10.1021/jo980089fSearch in Google Scholar

[39] J.A.N.F. Gomes, R.B. Mallion, Chem. Rev. 101, 1349 (2001) http://dx.doi.org/10.1021/cr990323h10.1021/cr990323hSearch in Google Scholar PubMed

[40] J.M. Schulman, R.L. Disch, J. Phys. Chem. A 101, 9176 (1997) http://dx.doi.org/10.1021/jp972391i10.1021/jp972391iSearch in Google Scholar

[41] H.J. Dauben Jr., J.D. Wilson, J.L. Laity, J. Am. Chem. Soc. 90, 811 (1968) http://dx.doi.org/10.1021/ja01005a05910.1021/ja01005a059Search in Google Scholar

Published Online: 2013-1-23
Published in Print: 2013-4-1

© 2013 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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