Abstract
Theoretical study about the magnetic properties of conjugated organic molecules containing borepin with π current density was carried out. 1-(2,4,6-Trimethylphenyl)borepin moiety is the center and other different groups are situated on the both β sides, which are named molecules 1–12 as theoretical model in order to establish the relationship between aromaticity and geometry variation of borepin. The optimized molecular structures of molecules 1–12 are almost keeping planar and the C2–C3 bond length of borepin turns longer from molecule 1 to molecule 12. Different borepin-annulated ring could change the conjugated effect of π-electron between borepin and these bore-pin-annulated rings. Moreover, the molecule presents antiaromaticity, in other words, the molecule became unstable when the C2–C3 bond length of borepin extended more than ca. 0.1417 nm. But the β position fragment and substituent groups of borepin are not affected in this case, they are still steady. However, the central borepin ring current is counteracted by symmetrical overlap of it with affiliated borepin-annulated ring current. Hence, the central borepin ring breaking would be liable to occur. These molecules have higher vertical ionization potentials(VIPs) and lower vertical electron affinities(VEAs), which suggests that these molecules could easily exist in anionic form.
Similar content being viewed by others
References
Li H., Jäkle F., Angew. Chem. Int. Ed., 2009, 48, 2313
Cheng S. H., Fan F. Y., Xu Y., Li S., Zhu P. W., Li H. D., Liu J. S., Chem. Res. Chinese Universities, 2013, 29(4), 816
Tan M., Lian G., Zhong X., Zhang S. J., Cui D. L., Wang Q. L., Chem. Res. Chinese Universities, 2012, 28(3), 387
Jakle F., Chem. Rev., 2010, 110, 3985
Hudnall T. W., Gabbai F. P., J. Am. Chem. Soc., 2007, 129, 11978
Liu X. Y., Bai D. R., Wang S., Angew. Chem. Int. Ed., 2006, 45, 5475
Matsumi N., Naka K., Chujo Y., J. Am. Chem. Soc., 1998, 120, 10776
Nagai A., Kokado K., Nagata Y., Chujo Y., Macromolecules, 2008, 41, 8295
Zhou G., Baumgarten M., Müllen K., J. Am. Chem. Soc., 2008, 130, 12477
Ashe III A. J., Klein W., Rousseau R., Organometallics, 1993, 12, 3225
Mercier L. G., Piers W. E., Parvez M., Angew. Chem. Int. Ed., 2009, 48, 6108
Caruso A. Jr., Siegler M. A., Tovar J. D., Angew. Chem. Int. Ed., 2010, 49, 4213
Subramanian G., Schleyer P. V. R., Jiao H. J., Organometallics, 1997, 16, 2362
Kassaee M. Z., Musavi S. M., Motamedi E., J. Theor. Comput. Chem., 2010, 9, 379
Jinguji A., Nakazawa R., Yagi T., Murata I., Tetrahedron, 1994, 50, 6495
Schulman J. M., Disch R. L., Organometallics, 2000, 19, 2932
Herndon W. C., J. Am. Chem. Soc., 1973, 95, 2404
Aihara J., J. Org. Chem., 1976, 41, 2488
Jug K., J. Org. Chem., 1983, 48, 1344
Dewar M. J. S., de Llano C., J. Am. Chem. Soc., 1969, 91, 789
Hess B. A. Jr., Schaad L. J., J. Am. Chem. Soc., 1971, 93, 305
Pople J. A., J. Chem. Phys., 1956, 24, 1111
Dauben H. J. Jr., Wilson J. D., Laity J. L., J. Am. Chem. Soc., 1969, 91, 1991
Benson R. C., Flygare W. H., J. Am. Chem. Soc., 1970, 92, 7523
Jusélius J., Sundholm D., Phys. Chem. Chem. Phys., 1999, 1, 3429
Morao I., Lecea B., Cossío F. P., J. Org. Chem., 1997, 62, 7033
Geuenich D., Hess K., Köhler F., Herges R., Chem. Rev., 2005, 105, 3758
Jusélius J., Sundholm D., Gauss J., J. Chem. Phys., 2004, 121, 3952
Lazzeretti P., Malagoli M., Zanasi R., Chem. Phys. Lett., 1994, 220, 299
Pelloni S., Lazzeretti P., Int. J. Quantum Chem., 2011, 111, 356
Faraday M., Philos. Trans. R. London, 1825, 115, 440
Rzepa H. S., Chem. Rev., 2005, 105, 3697
Schleyer P. V. R., Maerker C., Dransfeld A., Jiao H. J., Hommes N. J. R. V. E., J. Am. Chem. Soc., 1996, 118, 6317
Chen Z. F., Wannere C. S., Corminboeuf C., Puchta R., Schleyer P. V., Chem. Rev., 2005, 105, 3842
Bleeke J. R., Chem. Rev., 2001, 101, 1205
Schleyer P. V., Chem. Rev., 2001, 101, 1115
Becke A. D., Phys. Rev. A, 1988, 38, 3098
Reed A. E., Curtiss L. A., Weinhold F., Chem. Rev., 1988, 88, 899
Keith T. A., Bader R. F. W., J. Chem. Phys., 1993, 99, 3669
Zanasi R., J. Chem. Phys., 1996, 105, 1460
Bader R. F. W., Atoms in Molecules: A Quantum Theory, Clarendon Press, Oxford, 1990
Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., et al., Gaussian 09, Revision A.02, Gaussian Inc., Wallingford CT, 2009
Heine T., Corminboeuf C., Seifert G., Chem. Rev., 2005, 105, 3889
Li X. H., Yin G. X., Zhang X. Z., J. Mol. Struct.(Theochem.), 2010, 957, 61
Becke A. D., Edgekombe K. E., J. Chem. Phys., 1990, 92, 5397
Raúl M. A., Fernando M., Claudio O. A., Sebastián M. R., Patricio F., J. Phys. Chem. A, 2011, 115, 4397
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the National Natural Science Foundation of China(Nos.21003057, 21173096) and the Specialized Research Fund for the Doctoral Program of Higher Education of China(No.20110061110018).
Rights and permissions
About this article
Cite this article
Wei, W., Bai, Fq., Xia, Bh. et al. Theoretical analysis on magnetic properties of conjugated organic molecules containing borepin. Chem. Res. Chin. Univ. 29, 962–968 (2013). https://doi.org/10.1007/s40242-013-3129-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-013-3129-0