Skip to main content
SpringerLink
Log in

The effect of a heteroatom on the structure and vibrational spectra of Heteroannulated tetraphenylenes

  • Spectroscopy of Atoms and Molecules
  • Published:
Optics and Spectroscopy Aims and scope Submit manuscript

Abstract

Based on calculations by the DFT method, we have theoretically compared IR absorption and Raman spectra of tetraoxa[8]circulene (4O) and its analogs that contain sulfur (4S) and selenium (4Se) atoms. Calculations have shown that the structure of investigated molecules and observed shifts of similar vibrations in their IR and Raman spectra are interrelated. We have constructed correlation schemes of frequency shifts of normal vibrations upon passage from planar 4O circulene to its 4S and 4Se nonplanar analogs. The obtained data are of fundamental interest both from the point of view of specific selection rules and in the context of the novelty of the force field, where the conjugation of the internal and external macrocycles with heteroatoms manifests itself.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. V. Baryshnikov, B. F. Minaev, and V. A. Minaeva, Usp. Khim. 84 (5), 455 (2015).

    Article  Google Scholar 

  2. G. Baryshnikov, R. Valiev, N. Karaush, and B. Minaev, Phys. Chem. Chem. Phys. 16 (29), 15367 (2014).

    Article  Google Scholar 

  3. G. V. Baryshnikov, N. N. Karaush, and B. F. Minaev, Khim. Geterotsikl. Soedin. 50 (3), 349 (2014).

    Google Scholar 

  4. B. F. Minaev, G. V. Baryshnikov, and V. A. Minaeva, Comp. Theor. Chem. 972 (1–3), 68 (2011).

    Article  Google Scholar 

  5. R. Pop, M. Medeleanu, M. V. Diudea, B. Szefler, and J. Cioslowski, Cent. Eur. J. Chem. 11 (4), 527 (2013).

    Article  Google Scholar 

  6. M. V. Diudea, A. E. Vizitiu, T. Beu, A. Bende, C. L. Nagy, and D. J. Janežic, Mol. Struct. THEOCHEM. 904 (1–3), 28 (2009).

    Article  Google Scholar 

  7. J.-C. Charlier, T. W. Ebbesen, and Ph. Lambin, Phys. Rev. B 53 (16), 11108 (1996).

    Article  ADS  Google Scholar 

  8. G. Baryshnikov, B. Minaev, N. Karaush, and V. Minaeva, Phys. Chem. Chem. Phys. 16 (14), 6555 (2014).

    Article  Google Scholar 

  9. G. Baryshnikov, B. Minaev, N. Karaush, and V. Minaeva, RSC Adv. 4 (49), 25843 (2014).

    Article  Google Scholar 

  10. J. Yu, Q. Sun, Y. Kawazoe, and P. Jena, Nanoscale 6 (24), 14962 (2014).

    Article  ADS  Google Scholar 

  11. T. N. Gribanova, N. S. Zefirov, and V. I. Minkin, Doklady Chem. 426 (1), 105 (2009).

    Article  Google Scholar 

  12. T. N. Gribanova, N. S. Zefirov, and V. I. Minkin, Pure Appl. Chem. 82 (4), 1011 (2010).

    Article  Google Scholar 

  13. T. K. Mandal, D. Jose, A. Nijamudheen, and A. Datta, J. Phys. Chem. C 118 (23), 12115 (2014).

    Article  Google Scholar 

  14. X. Xiong, C.-L. Deng, B. F. Minaev, G. V. Baryshnikov, X.-S. Peng, and H. N. C. Wong, Chem. Asian J. 10 (4), 969 (2015).

    Article  Google Scholar 

  15. H. Erdtman and H.-E. Hogberg, Tetrahedron Lett. 11 (38), 3389 (1970).

    Article  Google Scholar 

  16. V. A. Minaeva, B. F. Minaev, G. V. Baryshnikov, H. Agren, and M. Pittelkow, Vib. Spectrosc. 61, 156 (2012).

    Article  Google Scholar 

  17. V. A. Minaeva, B. F. Minaev, G. V. Baryshnikov, O. M. Romeyko, and M. Pittelkow, Vib. Spectrosc. 65, 147 (2013).

    Article  Google Scholar 

  18. N. N. Karaush, B. F. Minaev, G. V. Baryshnikov, and V. A. Minaeva, Opt. Spectrosc. 116 (1), 33 (2014).

    Article  Google Scholar 

  19. V. A. Minaeva, B. F. Minaev, G. V. Baryshnikov, O. N. Romeyko, and M. Pittel’kov, J. Appl. Spectrosc. 79 (5), 695 (2012).

    Article  ADS  Google Scholar 

  20. A. D. Becke, J. Chem. Phys. 98 (7), 5648 (1993).

    Article  ADS  Google Scholar 

  21. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37 (2), 785 (1988).

    Article  ADS  Google Scholar 

  22. R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, J. Chem. Phys. 72 (1), 650 (1980).

    Article  ADS  Google Scholar 

  23. 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, Jr, 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, M. 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, and D. J. Fox, Gaussian 09, Revision A.02 (Gaussian, Inc., Wallingford, 2009).

    Google Scholar 

  24. P. L. Polavarapu, J. Phys. Chem. 94 (21), 8106 (1990).

    Article  Google Scholar 

  25. S. I. Gorelsky, SWizard program. http://www.sgchem. net/.

  26. G. Socrates, Infrared and Raman Characteristic Group Frequencies—Tables and Charts, 3rd ed. (Wiley, Chichester, 2001).

    Google Scholar 

  27. L. J. Bellamy, The Infra-Red Spectra of Complex Molecules (Methuen, London, 1954).

    Google Scholar 

  28. J. S. Kwiatkowski, J. Leszczynski, and I. Teca, J. Mol. Struct. 436, 451 (1997).

    Article  ADS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Khmelnitskii Cherkassy National University, Cherkassy, 18031, Ukraine

    V. A. Minaeva, G. V. Baryshnikov & B. F. Minaev

  2. Tomsk State University, Tomsk, 634050, Russia

    B. F. Minaev

  3. Laboratory of Engineering Plastics, Institute of Chemistry, Beijing, 100190, China

    B. F. Minaev

Authors
  1. V. A. Minaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. V. Baryshnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. F. Minaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Minaeva.

Additional information

Original Russian Text © V.A. Minaeva, G.V. Baryshnikov, B.F. Minaev, 2015, published in Optika i Spektroskopiya, 2015, Vol. 119, No. 4, pp. 604–616.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Minaeva, V.A., Baryshnikov, G.V. & Minaev, B.F. The effect of a heteroatom on the structure and vibrational spectra of Heteroannulated tetraphenylenes. Opt. Spectrosc. 119, 620–632 (2015). https://doi.org/10.1134/S0030400X15090192

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0030400X15090192

Keywords

Search

Navigation