Advertisement

Journal of Chemical Sciences

, Volume 120, Issue 1, pp 137–142 | Cite as

Expanded porphyrins as third order non-linear optical materials: Some structure-function correlations

  • Sabapathi Gokulnath
  • Tavarekere K. Chandrashekar
Article

Abstract

In this paper, the non-linear optical properties of representative core-modified expanded porphyrins have been investigated with an emphasis on the structure-property relationship between the aromaticity and conformational behaviour. It has been shown that the measured two-photon absorption cross section (σ 2) values depend on the structure of macrocycle, its aromaticity and the number of π-electrons in conjugation.

Keywords

Expanded porphyrins conjugation aromaticity conformation TPA cross section 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1. (a)
    For a recent highlight on expanded porphyrins see Sessler J L and Weghorn S J 1997 Expanded, contracted and isomeric porphyrins (Oxford: Elsevier) and references thereinGoogle Scholar
  2. 1. (b)
    Sessler J L and Weghorn S J 2000 Expanded Porphyrins In Porphyrin handbook (eds) K M Kadish, K M Smith and R Guilard (New York: Academic Press) vol II, chapter 9Google Scholar
  3. 1. (c)
    Lash T D 2000 Angew. Chem. Int. Ed. 39 1763CrossRefGoogle Scholar
  4. 2. (a)
    Ehrlich J E, Wu X L, Lee I-Y, Hu Z-Y, Rockel H, Marder S R and Perry J W 1997 Opt. Lett. 22 1843Google Scholar
  5. 2. (b)
    Kohler R H, Cao J, Zipfel W R, Webb W W and Hanson M R 1997 Science 276 2039CrossRefGoogle Scholar
  6. 2. (c)
    Kawata S, Sun H-B, Tanaka T and Takada K 2001 Nature (London) 412 697CrossRefGoogle Scholar
  7. 3. (a)
    Ahn T K, Kwon J H, Kim D Y, Cho D W, Jeong D H, Kim S K, Suzuki M, Shimizu S, Osuka A and Kim D 2005 J. Am. Chem. Soc. 127 12856CrossRefGoogle Scholar
  8. 3. (b)
    Yoon Z S, Kwon J H, Yoon M-C, Koh M K, Noh S B, Sessler J L, Lee J T, Seidel D, Aguilar A, Shimizu S, Suzuki M, Osuka A and Kim D 2006 J. Am. Chem. Soc. 128 14128CrossRefGoogle Scholar
  9. 4. (a)
    Ogawa K, Ohashi A, Kobuke Y, Kamada K and Ohta K 2003 J. Am. Chem. Soc. 125 13356CrossRefGoogle Scholar
  10. 4. (b)
    Drobizhev M, Stepanenko Y, Dzenis Y, Karotki A, Rebane A, Taylor P N and Anderson H L 2004 J. Am. Chem. Soc. 126 15352CrossRefGoogle Scholar
  11. 4. (c)
    Drobizhev M, Stepanenko Y, Dzenis Y, Karotki A, Rebane A, Taylor P N and Anderson H L 2005 J. Phys. Chem. B109 7223Google Scholar
  12. 5.
    For recent studies on TPA cross on porphyrins see (a) Mori S, Kim K S, Yoon Z S, Noh S B, Kim D and Osuka A 2007 J. Am. Chem. Soc. 129 11344CrossRefGoogle Scholar
  13. 5. (b)
    Yoon M-C, Noh S B, Tsuda A, Nakamura Y, Osuka A and Kim D 2007 J. Am. Chem. Soc. 129 10080CrossRefGoogle Scholar
  14. 5. (c)
    Hisaki I, Hiroto S, Kim K S, Noh S B, Kim D, Shinokubo H and Osuka A 2007 Angew. Chem. Int. Ed. 46 5125CrossRefGoogle Scholar
  15. 6. (a)
    Chandrashekar T K and Venkatraman S 2003 Acc. Chem. Res. 36 676CrossRefGoogle Scholar
  16. 6. (b)
    Rath H, Sankar J, PrabhuRaja V, Chandrashekar T K, Joshi B S and Roy R 2005 Chem. Commun. 3343Google Scholar
  17. 7. (a)
    Rath H, Sankar J, PrabhuRaja V, Chandrashekar T K and Joshi B S 2005 Org. Lett. 7 5445CrossRefGoogle Scholar
  18. 6. (b)
    Misra R, Kumar R, Chandrashekar T K and Suresh E 2007 Chem. Commun. 43Google Scholar
  19. 8. (a)
    Rath H, Sankar J, PrabhuRaja V, Chandrashekar T K, Nag A and Goswami D 2005 J. Am. Chem. Soc. 127 11608CrossRefGoogle Scholar
  20. 8. (b)
    Rath H, Sankar J, PrabhuRaja V, Chandrashekar T K, Nag A, Goswami D and Joshi B S 2006 Org. Lett. 8 2325CrossRefGoogle Scholar
  21. 9. (a)
    Misra R, Kumar R, Chandrashekar T K, Suresh C H, Nag A and Goswami D 2006 J. Am. Chem. Soc. 128 16083CrossRefGoogle Scholar
  22. 9. (b)
    Misra R, Kumar R, Chandrashekar T K, Nag A and Goswami D 2006 Org. Lett. 8 629CrossRefGoogle Scholar
  23. 9. (c)
    Kumar R, Misra R, Chandrashekar T K, Nag A Goswami D, Suresh E and Suresh C H 2007 Eur. J. Org. Chem. 4552Google Scholar
  24. 10. (a)
    Narayanan S J, Sridevi B, Chandrashekar T K, Vij A and Roy R 1998 Angew. Chem. Int. Ed. 37 3394CrossRefGoogle Scholar
  25. 10. (b)
    Narayanan S J, Sridevi B, Chandrashekar T K, Viji A and Roy R 1999 J. Am. Chem. Soc. 121 9053CrossRefGoogle Scholar
  26. 11. (a)
    Narayanan S J, Sridevi B and Chandrashekar T K 1999 Org. Lett. 1 587CrossRefGoogle Scholar
  27. 11. (b)
    Rath H, Anand V G, Sankar J, Venkatraman, Chandrashekar T K, Joshi B S, Khetrapal C L, Schilde U and Senge M O 2003 Org. Lett. 5 3531CrossRefGoogle Scholar
  28. 12. (a)
    Srinivasan A, Anand V G, Narayanan S J, Pushpan S K, Kumar M R Chandrashekar T K Sugiura K-I and Sakata Y 1999 J. Org. Chem. 64 8693CrossRefGoogle Scholar
  29. 12. (b)
    Narayanan S J, Srinivasan A, Sridevi B, Chandrashekar T K, Senge M O, Sugiura K-I and Sakata Y 2000 Eur. J. Org. Chem. 2357Google Scholar
  30. 13.
    Sengupta P, Balaji J, Banerjee S, Philip R, Ravindra K G and Maiti S 2000 J. Chem. Phys. 112 9201CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2008

Authors and Affiliations

  • Sabapathi Gokulnath
    • 1
  • Tavarekere K. Chandrashekar
    • 1
  1. 1.Department of ChemistryIndian Institute of TechnologyKanpurIndia

Personalised recommendations