Abstract
The photophysics and electronic structure of tribenzotetraazachlorins (H2, Zn, and Mg), which are novel analogues of phtalocyanines, have been studied experimentally and theoretically. At 293 K, the electronic absorption, fluorescence, and fluorescence excitation spectra are recorded and the fluorescence quantum yield and lifetime, as well as the quantum yield of singlet oxygen generation, are measured; at 77 K, the fluorescence, fluorescence excitation, and fluorescence polarization spectra are recorded and the fluorescence lifetime values are measured. The dependences of the absorption spectra and photophysical parameters on the structure variation are analyzed in detail. Quantum-chemical calculations of the electronic structure and absorption spectra of tribenzotetraazachlorins (H2, Mg) are performed using the INDO/Sm method (modified INDO/S method) based on molecular-geometry optimization by the DFT PBE/TZVP method. The results of quantum-chemical calculations of the electronic absorption spectra are in very good agreement with the experimental data for the transitions to two lower electronic states.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. Sorokin, Chem. Rev. 113, 8152 (2013).
R. Bonnett, Chemical Aspects of Photodynamic Therapy (Gordon and Breach Science, Amsterdam, 2000), p. 199.
H. Ali and J. E. van Lier, in Handbook of Porphyrin Science, Ed. by K. M. Kadish, K. M. Smith, and R. Guilard (World Scientific, Singapore, 2010), Vol. 4, p. 1.
G. de la Torre, M. Nicolau, and T. Torres, in Supramolecular Photosensitive and Electroactive Materials, Ed. by H. S. Nalwa (Academic, San Diego, 2001), p. 1.
D. Wöhrle, L. Kreienhoop, and D. Schlettwein, in Phthalocyanines: Properties and Applications, Ed. by C. C.Leznoff and A. B. P. Lever (VCH, New York, 1996), Vol. 4, p. 219.
D. Schlettwein and T. Nyokong, in Handbook of Porphyrin Science, Ed. by K. M. Kadish, K. M. Smith, and R. Guilard (World Scientific, Singapore, 2012), Vol. 24, p. 389.
F. D’Souza and O. Ito, Chem. Soc. Rev. 41, 86 (2012).
M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, Coord. Chem. Rev. 219–221, 235 (2001).
E. Makarova and E. A. Luk’yanets, J. Porphyr. Phthalocyan. 13, 188 (2009).
E. A. Makarova and E. A. Luk’yanets, in Achievements in Porphyrine Chemistry, Ed. by O. A. Golubchikov (NII Khim. SPbGU, St. Petersburg, 2007), Vol. 5, p. 28 [in Russian].
T. Fukuda and N. Kobayashi, Dalton Trans., No. 35, 4685 (2008).
S. V. Dudkin, E. A. Makarova, and E. A. Luk’yanets, Russ. Chem. Rev. 85, 700 (2016).
E. A. Makarova, G. V. Koroleva, and E. A. Luk’yanets, Russ. J. Gen. Chem. 71, 821 (2001).
E. A. Makarova, G. V. Koroleva, and E. A. Luk’yanets, RF Patent No. 2188200 (2002).
T. Fukuda, E. A. Makarova, E. A. Lukyanets, and N. Kobayashi, Chem. Eur. J. 10, 117 (2004).
E. A. Makarova, T. Fukuda, E. A. Lukyanets, and N. Kobayashi, Chem. Eur. J. 11, 1235 (2005).
E. A. Makarova, E. V. Dzyuina, T. Fukuda, H. Kaneko, N. Hashimoto, Y. Kikukawa, N. Kobayashi, and E. A. Lukyanets, Inorg. Chem. 48, 164 (2009).
V. N. Nemykin and E. A. Lukyanets, in Handbook of Porphyrin Science, Ed. by K. M. Kadish, K. M. Smith, and R. Guilard (World Scientific, Singapore, 2010), Vol. 13, p. 1.
V. N. Nemykin, S. V. Dudkin, F. Dumoulin, C. Hirel, A. G. Gurek, and V. Ahsen, Arkivoc 2014, 142 (2014).
V. N. Nemykin and E. A. Lukyanets, Arkivoc 2010, 136 (2010).
E. A. Lukyanets and V. N. Nemykin, J. Porphyr. Phthalocyan. 14, 1 (2010).
I. K. Shushkevich, P. P. Pershukevich, E. A. Makarova, and K. N. Solovyov, J. Appl. Spectrosc. 68, 767 (2001).
P. P. Pershukevich, V. A. Galievsky, A. S. Stasheuski, E. A. Makarova, E. A. Luk’yanets, and K. N. Solovyov, J. Appl. Spectrosc. 77, 790 (2010).
S. M. Arabei, J.-P. Galaup, A. P. Stupak, T. A. Pavich, E. A. Makarova, and K. N. Solovyov, J. Appl. Spectrosc. 76, 352 (2009).
E. A. Makarova, S. V. Dudkin, and E. A. Lukyanets, J. Porphyr. Phthalocyan. 17, 785 (2013).
V. A. Kuzmitsky, E. A. Makarova, P. P. Pershukevich, I. K. Shushkevich, K. N. Solovyov, and V. B. Tusov, Chem. Phys. 298, 1 (2004).
P. P. Pershukevich, D. I. Volkovich, L. L. Gladkov, S. V. Dudkin, A. P. Stupak, V. A. Kuzmitsky, E. A. Makarova, and K. N. Solovyov, Opt. Spectrosc. 117, 722 (2014).
J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett. 77, 3865 (1996).
D. N. Laikov, Chem. Phys. Lett. 281, 151 (1997).
L. L. Gladkov, V. V. Gromak, and V. K. Konstantinova, J. Appl. Spectrosc. 74, 328 (2007).
D. I. Volkovich, L. L. Gladkov, V. A. Kuzmitsky, and K. N. Solovyov, J. Appl. Spectrosc. 78, 155 (2011).
V. N. Knyukshto, D. I. Volkovich, L. L. Gladkov, V. A. Kuzmitsky, A. Ul-Haque, I. A. Popkova, P. A. Stuzhin, and K. N. Solovyov, Opt. Spectrosc. 113, 359 (2012).
L. L. Gladkov and V. V. Gromak, J. Appl. Spectrosc. 79, 854 (2012).
V. A. Kuzmitsky and D. I. Volkovich, J. Appl. Spectrosc. 75, 27 (2008).
M. V. Belkov, A. A. Grishchuk, S. V. Dudkin, E. A. Makarova, P. P. Pershukevich, and K. N. Solovyov, J. Appl. Spectrosc. 77, 213 (2010).
V. A. Kuzmitsky, Opt. Spectrosc. 101, 666 (2006).
S. M. Arabei, V. A. Kuzmitsky, and K. N. Solovyov, Opt. Spectrosc. 102, 692 (2007).
S. M. Arabei, V. A. Kuzmitsky, and K. N. Solovyov, Chem. Phys. 352, 197 (2008).
W. Freyer, S. Mueller, and K. Teuchner, J. Photochem. Photobiol., A 163, 231 (2004).
S. S. Dvornikov, V. N. Knyukshto, V. A. Kuzmitsky, A. M. Shulga, and K. N. Solovyov, J. Lumin. 23, 373 (1981).
V. A. Chernyavskii, P. P. Pershukevich, I. K. Shushkevich, E. A. Makarova, and K. N. Solovyev, J. Appl. Spectrosc. 76, 672 (2009).
V. A. Kuz’mitskii, K. N. Solov’ev, and M. P. Tsvirko, in Porphyrines: Spectroscopy, Electrochemistry, Application, Ed. by N. S. Enikolopyan (Nauka, Moscow, 1987), p. 7 [in Russian].
E. I. Sagun, A. P. Losev, and I. N. Nichiporovich, Dokl. Akad. Nauk BSSR 31, 416 (1987).
M. Gouterman, in The Porphyrins, Ed. by D. V. Dolphin III (Academic, New York, 1978), p. 1.
K. N. Solovyev and E. A. Borisevich, Phys. Usp. 48, 231 (2005).
M. V. Bel’kov, E. A. Makarova, P. P. Pershukevich, and K. N. Solovyov, J. Appl. Spectrosc. 82, 188 (2015).
Yu. B. Vysotsky, V. A. Kuzmitsky, and K. N. Solovyov, Theor. Chim. Acta 59, 467 (1981).
M. Gouterman, J. Mol. Spectrosc. 6, 138 (1961).
V. A. Kuz’mitskii, Preprint No. 188 (Inst. Phys. Acad. Sci. Belorus. SSR, Minsk, 1979).
A. V. Luzanov, Russ. Chem. Rev. 49, 1033 (1980).
K. N. Solovyov, P. A. Stuzhin, V. A. Kuzmitsky, D. I. Volkovich, V. N. Knyukshto, E. A. Borisevich, and A. Ul-Haque, Makroheterotsikly 3, 51 (2010).
V. N. Nemykin, R. G. Hadt, R. V. Belosludov, H. Mizuseki, and Y. Kawazoe, J. Phys. Chem. A 111, 12901 (2007).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © P.P. Pershukevich, D.I. Volkovich, L.L. Gladkov, S.V. Dudkin, V.A. Kuzmitsky, E.A. Makarova, K.N. Solovyev, 2017, published in Optika i Spektroskopiya, 2017, Vol. 123, No. 4, pp. 518–535.
Rights and permissions
About this article
Cite this article
Pershukevich, P.P., Volkovich, D.I., Gladkov, L.L. et al. The effect of annulation of benzene rings on the photophysics and electronic structure of tetraazachlorin molecules. Opt. Spectrosc. 123, 535–551 (2017). https://doi.org/10.1134/S0030400X17100198
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0030400X17100198