The spectral and luminescent properties of 21-thia- and 21,23-dithia-5,10,15,20-tetraphenylporphyrin were studied in solutions at 293 K. The origin of the spectral shifts of the absorption bands upon heterosubstitution was discussed based on the Gouterman four-orbital model. Fluorescence quenching of the heteroporphyrins was shown to be due to an internal heavy-atom effect of the thiophene-ring heteroatom.
Similar content being viewed by others
References
L. Latos-Grazynski, in: The Porphyrin Handbook, K. M. Kadish, K. M. Smith, and R. Guillard (Eds.), New York (2000), pp. 361–416.
I. Gupta and M. Ravikanth, Coord. Chem. Rev., 250, 468–518 (2006).
T. Chatterjee, V. S. Shetti, R. Sharma, and M. Ravikanth, Chem. Rev., 117, 3254–3328 (2016).
M. J. Broadhurst, R. Grigg, and A. V. Johnson, J. Chem. Soc. D, 1480–1482 (1969).
M. J. Broadhurst, R. Grigg, and A. V. Johnson, J. Chem. Soc. D, 807–809 (1970).
M. J. Broadhurst, R. Grigg, and A. V. Johnson, J. Chem. Soc. C, 3681–3690 (1971).
R. P. Pandian, T. K. Chendrasekar, G. S. S. Saini, and A. L. Verma, J. Chem. Soc., Faraday Trans., 89, 677–682 (1993).
P. G. Van Patten, A. P. Shreve, J. S. Lindsey, and R. J. Donohoe, J. Phys. Chem. B, 102, 4209–4216 (1998).
B. Sridevi, S. J. Narayanan, A. Shrinivasan, M. V. Reddy, and T. K. Chandrasekar, J. Porphyrins Phthalocyanines, 2, 69–78 (1998).
S. Rai and M. Ravikanth, Tetrahedron, 63, 2455–2465 (2007).
C. E. Stilts, M. I. Nelen, D. G. Hilmey, S. R. Davies, S. O. Gollnick, A. R. Oseroff, S. L. Gibson, R. Hilf, and M. R. Detty, J. Med. Chem., 43, 2403–2410 (2000).
D. G. Hilmey, M. Abe, M. I. Nelen, C. E. Stilts, G. A. Baker, S. N. Baker, F. V. Bright, S. R. Davies, S. O. Gollnick, A. R. Oseroff, S. L. Gibson, R. Hilf, and M. R. Detty, J. Med. Chem., 45, 449–461 (2002).
Y. You, S. L. Gibson, R. Hilf, S. R. Davies, A. R. Oserfoff, I. Roy, T. Y. Ohulchanskyy, E. J. Bergey, and M. R. Detty, J. Med. Chem., 46, 3734–3747 (2003).
T. Higashino and H. Imahori, Dalton Trans., 44, 448–463 (2015).
J. S. Linsdey, S. Prathapan, T. E. Johnson, and R. W. Wagner, Tetrahedron, 50, 8941–8968 (1994).
R. P. Pandian, D. Reddy, N. Chidambaram, and T. K. Chandrashekar, Chem. Sci., 102, 307–318 (1990).
J. N. Demas and G. A. Crosby, J. Phys. Chem., 75, 991–1024 (1971).
I. V. Vershilovskaya, S. Stefani, P. Verstappen, T. H. Ngo, I. G. Scheblykin, W. Dehaen, W. Maes, and M. M. Kruk, Macroheterocycles, 10, 257–267 (2017).
B. D. Berezin and D. B. Berezin, Modern Organic Chemistry Course [in Russian], Vysshaya Shkola, Moscow (1999).
M. Gouterman, in: The Porphyrins, Vol. 3, D. Dolphin (Ed.), New York (1978), pp. 1–165.
E. S. Lyul’kovich and N. N. Kruk, Tr. BGTU, Fiz.-Mat. Nauki Inf., 6, 63–67 (2015).
T. Bruhn and C. Bruckner, Phys. Chem. Chem. Phys., 17, 3560–3569 (2015).
R. P. Pandian, D. Reddy, N. Chidambaram, and T. K. Chandrasekhar, Proc. Indian Acad. Sci., Chem. Sci., 102, 307–315 (1990).
S. L. Murov, I. Carmichael, and G. L. Hug, Handbook of Photochemistry, 2nd edn., New York (1993).
S. P. McGlynn, T. Azumi, and M. Kinoshita, Molecular Spectroscopy of the Triplet State, Prentice-Hall International Series in Chemistry, Prentice-Hall, Englewood Cliffs, N. J. (1969), 433 pp.
N. N. Kruk, Structure and Optical Properties of Tetrapyrrole Compounds [in Russian], BGTU, Minsk (2019).
D. J. Quimby and F. R. Longo, J. Am. Chem. Soc., 94, 5112–5117 (1975).
G. D. Egorova, V. N. Knyukshto, K. N. Solov’ev, and M. P. Tsvirko, Opt. Spektrosk., 48, 1101–1109 (1980).
V. N. Knyukshto, K. N. Solovyov, and G. D. Egorova, Biospectroscopy, 4, 121–133 (1998).
E. G. Azenha, A. C. Serra, M. Pineiro, M. M. Pineira, J. Seixas de Melo, L. G. Arnaut, S. J. Fromosinho, and A. M. d’A. Rocha Gonsalves, Chem. Phys., 280, 177–190 (2002).
K. N. Solov’ev and E. A. Borisevich, Usp. Fiz. Nauk, 175, 247–270 (2005).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 87, No. 2, pp. 181–188, March–April, 2020.
Rights and permissions
About this article
Cite this article
Vershilovskaya, I.V., Liulkovich, L.S., Pukhovskaya, S.G. et al. Heteroatom Role in the Formation of Spectral-Luminescent Properties of 21-Thia- and 21,23-Dithia-5,10,15,20-Tetraphenylporphyrin in Solutions. J Appl Spectrosc 87, 201–207 (2020). https://doi.org/10.1007/s10812-020-00984-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10812-020-00984-6