John MACK, Martijn WILDERVANCK, Tebello NYOKONG

4122

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis. Recent attempts to prepare fused-ring-expanded aza-BODIPY analogues with benzene, pyrazine, and naphthalene rings have demonstrated that the properties of aza-BODIPYs vary markedly when different fused ring systems are added to the b-carbons of the pyrrole rings. A comparison of the TD-DFT calculations demonstrates that, as has previously been postulated, trends in the optical spectra, redox properties, and electronic structures of aza-BODIPYs follow those observed for the phthalonitrile precursors and the analogous phthalocyanines despite the absence of a fully conjugated macrocyclic perimeter that obeys Hückel's rule.
Anahtar Kelimeler:

TD-DFT calculations, phthalocyanines, aza-BODIPYs

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis. Recent attempts to prepare fused-ring-expanded aza-BODIPY analogues with benzene, pyrazine, and naphthalene rings have demonstrated that the properties of aza-BODIPYs vary markedly when different fused ring systems are added to the b-carbons of the pyrrole rings. A comparison of the TD-DFT calculations demonstrates that, as has previously been postulated, trends in the optical spectra, redox properties, and electronic structures of aza-BODIPYs follow those observed for the phthalonitrile precursors and the analogous phthalocyanines despite the absence of a fully conjugated macrocyclic perimeter that obeys Hückel's rule.
Keywords:

TD-DFT calculations, phthalocyanines, aza-BODIPYs,

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  • Bandichhor, R.; Petrescu, A. D.; Vespa, A.; Kier, A. B.; Schroeder, F.; Burgess, K. J. Am. Chem. Soc. 2006, 128, 10688–10689.
  • Du, P. W.; Lippard, S. J. Inorg. Chem. 2010, 49, 10753–10755.
  • Ali, H.; van Lier, J. E. In Handbook of Porphyrin Science, Vol. 4; Kadish, K. M.; Smith, K. M.; Guilard, R. Eds. World Scientific: Singapore, 2010, pp. 1–119.
  • Nyokong, T.; Ahsen, V. Eds. Photochemical and Photophysical Characterization, in Photosensitizers in Medicine, Environment, and Security; Springer: New York, NY, USA, 2012.
  • Kobayashi, N.; Nakajima, S.; Osa, T. Inorg. Chim. Acta 1993, 210, 131–133.
  • Kobayashi N.; Nakajima, S.; Ogata, H.; Fukuda, T. Chem. Eur. J. 2004, 10, 6294–6312.
  • Gorman, A.; Killoran, J.; O’Shea, C.; Kenna, T.; Gallagher, W. M.; O’Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619–10631.
  • McDonnell, S. O.; Hall, M. J.; Allen, L. T.; Byrne, A.; Gallagher, W. M.; O’Shea, D. F. J. Am. Chem. Soc. 2005, 127, 16360–16361.
  • Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 12162–12163.
  • Yang, Y.; Guo, Q.; Chen, H.; Zhou, Z.; Guo, Z.; Shen, Z. Chem. Commun. 2013, 49, 3940–3942.
  • Lu, H.; Mack, J.; Yang, Y.; Shen, Z. Chem. Soc. Rev. 2014, 43, 4778–4823.
  • Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891–4932.
  • Lu, H.; Shimizu, S.; Mack, J.; You, X. Z.; Shen, Z.; Kobayashi, N. Chem. Asian J. 2011, 6, 1026–1037.
  • Liu, H.; Mack, J.; Guo, Q.; Kobayashi, N.; Shen, Z. Chem. Commun. 2011, 47, 12092–12094.
  • Mack, J.; Asano, Y.; Kobayashi, N. Stillman, M. J. J. Am. Chem. Soc. 2005, 127, 17697–17711.
  • Michl, J. J. Am. Chem. Soc. 1978, 100, 6801–6811.
  • Michl, J. J. Am. Chem. Soc. 1978, 100, 6812–6818.
  • Michl, J. Pure Appl. Chem. 1980, 52, 1549–1563.
  • Michl, J. Tetrahedron 1984, 40, 3845–3934.
  • Magyar, R. J.; Tretiak, S. J. J. Chem. Theory Comput. 2007, 3, 976–987.
  • Cai, Z. L.; Crossley, M. J.; Reimers, J. R.; Kobayashi, R; Amos, R. D. J. Phys. Chem. B 2006, 110, 15624–15632.
  • Nemykin, V. N.; Hadt, R. G.; Belusludov, R. V.; Mizuseki, H.; Kawazoe Y. J. Phys. Chem. A 2007, 111, 12901– 129
  • Gouterman, M. In The Porphyrins, Vol. 3, Part A; Dolphin, D. Ed. Academic Press: New York, NY, USA, 1978, pp. 1–165.
  • Lash, T. D. J. Porphyrins Phthalocyanines 2001, 5, 267–288.
  • Xu, H. J.; Mack, J.; Descalzo, A. B.; Shen, Z.; Kobayashi, N.; You, X. Z.; Rurack, K. Chem. Eur. J. 2011, 17, 8965–8983.
  • Xu, H. J.; Mack, J.; Wu, D.; Xue, Z. L.; Descalzo, A. B.; Rurack, K.; Kobayashi, N.; Shen, Z. Chem. Eur. J. 2012, 18, 16844–16867.
  • Blackburn, E. V.; Timmons, C. J. J. Chem. Soc. C 1970, 175–178.
  • Cammidge, A. N.; Gopee, H. Chem. Eur. J. 2006, 12, 8609–8613.
  • Cammidge, A. N.; Gopee, H. Chem. Commun. 2002, 966–967.
  • Galpern, M. G.; Luk’yanets, E. A. Zh. Obshch. Khim. 1969, 39, 2536–2541.
  • Galpern, M. G.; Luk’yanets, E. A. Zh. Obsch. Khim. 1971, 41, 2549–2552.
  • Kudrevich, S.V.; van Lier, J. E.; Galpern, M. G.; Luk’yanets, E. A. Can. J. Chem. 1996, 74, 508–515.
  • Kudrevich, S.V.; van Lier, J. E. Can. J. Chem. 1996, 74, 1718–1723.
  • Kopecky, K.; Novakova, V.; Miletin, M.; Kuˇcera, R.; Zimcik, P. Bioconjugate Chem. 2010, 21, 1872–1879.
  • Kopecky, K.; Novakova, V.; Miletin, M.; Kuˇcera, R.; Zimcik, P. Tetrahedron 2011, 67, 5956–5963.
  • Zimcik, P.; Novakova, V.; Kopecky, K.; Miletin, M.; Zeynep, R.; Kobak, U. Inorg. Chem. 2012, 51, 4215–4223.
  • Novakova, V.; Miletin, M.; Filandrov´a, T.; Lencˇo, J.; Ruˇziˇcka, A.; Zimcik, P. J. Org. Chem. 2014, 79, 2082–2093. ◦
  • Faust, R.; Weber, C. J. Org. Chem. 1999, 64, 2571–2573.
  • L¨oser, P.; Winzenburg, A.; Faust, R. Chem. Commun. 2013, 49, 9413–9415.
  • Engelhardt, V.; Kuhri, S.; Fleischhauer, J.; Garc´ıa-Iglesias, M.; Gonz´alez-Rodr´ıguez, D.; Bottari, G.; Torres, T.; Guldi, D. M.; Faust, R. Chem. Sci. 2013, 4, 3888–3893.
  • Rusanova, J.; Pilkington, M.; S. Decurtins, S. Chem. Commun. 2002, 2236–2237.
  • Rio, Y.; Seitz, W.; Gouloumis, A.; V´azquez, P.; Sessler, J. L.; Guldi, D. M.; Torres, T. Chem. Eur. J. 2010, 16, 1929–1940.
  • G¨ol, C.; Malko¸c, M.; Ye¸silot, S.; Durmu¸s, M. Dalton Trans. 2014, 43, 7561–7569.
  • G¨ol, C.; Malko¸c, M.; Ye¸silot, S.; Durmu¸s, M. Dyes Pigments 2014, 111, 81–90.
  • 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 D.01; Gaussian, Inc.: Wallingford, CT, USA, 2009.
  • Eisner, U.; Linstead, R. P. J. Chem. Soc. 1955, 3749–3754.
  • Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138–163.
  • Kopranenkov, V. N.; Daskevich, S. N.; Luk’yanets, E. A. Zh. Obsch. Khim. 1979, 49, 1408–1412.
  • Yamada, H.; Kuzuhara, D.; Takahashi, T.; Shirnizu, Y.; Uota, K.; Okujima, T.; Uno, H.; Ono, N. Org. Lett. 2008, 10, 2947–2950.
  • Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998–4010.
  • Linstead, R. P.; Whalley, M. J. Chem. Soc. 1952, 4839–4846.
  • Whalley, M. J. Chem. Soc. 1961, 866–869.
  • Kobayashi, N.; Mack, J.; Ishii, K.; Stillman, M. J. Inorg. Chem. 2002, 41, 5350–5363.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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