View PDF Version
 
DOI: 10.1039/A708892B (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 779-784

Synthesis and non-linear optical properties of (N-alkylpyrrol-2-yl)squaraine derivatives. Part 2[hair space]†

(Note: The full text of this document is currently only available in the PDF Version )

Daniel E. Lynch, Ian R. Peterson, Mathias Floersheimer, Dominik Essing, Li-feng Chi, Harald Fuchs, Nicholas J. Calos, Barry Wood, Colin H. L. Kennard and G. John Langley

Abstract

Two squaraine dyes, bis(5-ethyl-1-octadecylpyrrol-2-yl)squaraine (Et-Py) and bis(3,5-dimethyl-4-ethyl-1-octadecylpyrrol-2-yl)squaraine (MeEt-Py) have been synthesised and studied as Langmuir–Blodgett (LB) monolayers using atomic force microscopy (AFM), angle dependent X-ray photoelectron spectroscopy (ADXPS) and grazing incidence X-ray diffraction (GIXD). Additional investigations include both their linear and second-order non-linear optical properties, the latter giving deff = 1.5 ± 0.2 pm V–1 for Et-Py and 1.1 ± 0.2 pm V–1 for MeEt-Py. Comparisons with the previously reported dyes, bis(1-octadecylpyrrol-2-yl)squaraine (Py) and bis(3,5-dimethyl-1-octadecylpyrrol-2-yl)squaraine (Me-Py) reveal that Me-Py is the only one of the four which deposits as ordered, densely packed LB films which allows further studies on Me-Py so as to ascertain a valid mechanism for the occurrence of second harmonic generation (SHG) in these centrosymmetric molecules. The results presented demonstrate that the experimentally observed SHG in squaraines arises from a surface induced orientational effect where higher SHG is achieved if the squaraine head-group is essentially perpendicular to the required hydrophilic substrate.

References

  1. B. Patrick, M. V. George, P. V. Kamat, S. Das and K. G. Thomas, J. Chem. Soc., Faraday Trans., 1992, 88, 671 RSC.
  2. S. Das, K. G. Thomas, P. V. Kamat and M. V. George, Proc. Indian Acad. Sci., Chem. Sci., 1993, 105, 513 Search PubMed.
  3. K.-Y. Law, Chem. Rev., 1993, 93, 449 CrossRef CAS.
  4. A. Treibs and K. Jacob, Angew. Chem., Int. Ed. Engl., 1965, 4, 694 CrossRef.
  5. E. E. Havinga, W. ten Hoeve and H. Wynberg, Synth. Met., 1993, 55, 299 CrossRef CAS.
  6. Y.-Y. Chen and H. K. Hall, Polym. Bull. (Berlin), 1986, 16, 419 Search PubMed.
  7. D. E. Lynch, U. Geissler, J. Kwiatowski and A. K. Whittaker, Polym. Bull. (Berlin), 1997, 38, 493 Search PubMed.
  8. D. E. Lynch, U. Geissler, I. R. Peterson, M. Floersheimer, R. Terbrack, L. F. Chi, H. Fuchs, N. J. Calos, B. Wood, C. H. L. Kennard and G. J. Langley, J. Chem. Soc., Perkin Trans. 2, 1997, 827 RSC.
  9. K.-Y. Law and C. C. Chen, J. Phys. Chem., 1989, 93, 2533 CrossRef CAS.
  10. Y. Kawabata, T. Sekiguchi, M. Tanaka, T. Nakamura, H. Komizu, K. Honda and E. Manda, J. Am. Chem. Soc., 1985, 107, 5270 CrossRef CAS.
  11. R. Gilardi and J. L. Flippen-Anderson, Acta Crystallogr., Sect. C, 1985, 41, 591 CrossRef.
  12. C. H. MacGillavry and M. Wolthius-Spuy, Acta Crystallogr., Sect. B, 1970, 26, 645 CrossRef CAS.
  13. T. L. Marshbanks, H. K. Jugduth, W. N. Deglass and E. I. Franses, Thin Solid Films, 1993, 232, 126 CrossRef CAS.
  14. T. J. Sarapatka, Thin Solid Films, 1993, 226, 219 CrossRef CAS.
  15. S. C. Nyburg and A. R. Gerson, Acta Crystallogr., Sect. B, 1992, 48, 103 CrossRef.
  16. G. J. Langley, E. Hecquet, I. P. Morris and D. G. Hamilton, Rapid Commun. Mass Spectrosc., 1997, 11, 165 CrossRef CAS.
  17. J. L. Brédas and F. Meyers, Nature (London), 1995, 375, 362 CAS.
  18. G. Ashwell, Adv. Mater., 1996, 8, 248 CAS.
  19. G. J. Ashwell, G. S. Bahra, C. R. Brown, D. G. Hamilton, C. H. L. Kennard and D. E. Lynch, J. Mater. Chem., 1996, 6, 23 RSC.
  20. D. G. Hamilton, D. E. Lynch and G. Smith, Aust. J. Chem., 1996, 49, 1339 CAS.
  21. T. Yamada, H. Hoshi, K. Ishikawa, H. Takezoe and A. Fukuda, Jpn. J. Appl. Phys., 1995, 34, L-229.
  22. G. J. Ashwell, G. Jefferies, D. G. Hamilton, D. E. Lynch, M. P. S. Roberts, G. S. Bahra and C. R. Brown, Nature (London), 1995, 375, 385 CrossRef CAS.
  23. R. T. Bailey, F. R. Cruickshank, P. J. Halfpenny, D. Pugh, J. N. Sherwood and G. S. Simpson, in Principles and Applications of Nonlinear Optical Materials, ed. R. W. Munn and C. N. Ironside, Blackie Academic and Professional, London, 1993, p. 146 Search PubMed.
  24. I. R. Girling, N. A. Cade, P. V. Kolinski, J. D. Earls and G. H. Cross, Thin Solid Films, 1985, 132, 101 CrossRef CAS.
  25. J. C. Ashley, IEEE Trans. Nucl. Sci., 1980, 27, 1454.
  26. T. L. Marshbanks, H. K. Jugduth, W. N. Deglass and E. I. Franses, Thin Solid Films, 1993, 232, 126 CrossRef CAS.
  27. G. J. Foran, J. B. Peng, R. Steitz, G. T. Barnes and I. R. Gentle, Langmuir, 1996, 12, 774 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.