Abstract

The chain-length dependences of static third-order hyperpolarizabilities γSTAT of the homologous series of thiacyanines, of their meso-nitrogen-substituted derivatives, and of simple bis(dimethylamino)methine dyes are determined from nondegenerate four-wave mixing dispersion curves. We determined nearly the same very rapid increase of γSTAT with growing numbers of π electrons of the chain (γSTAT-N8±2) for both the thiacyanine and the bis(dimethylamino)methine series, an alternating influence of meso-nitrogen substitution for even and for odd double bonds of the chain, and a saturation of the hyperpolarizability for the longest thiacyanine (thiatricarbocyanine). We discuss our results, taking into account semiempirical quantum chemical calculations.

© 1998 Optical Society of America

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  46. G. Heilig and W. Lüttgke, Chem. Ber. 119, 3102–3108 (1986);Chem. Ber. 121, 407–410 (1988).
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1997 (1)

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

1996 (2)

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, and H.-H. Johannes, Chem. Phys. Lett. 266, 99–106 (1996).
[Crossref]

T. W. Johr, W. Werncke, L. Dähne, M. Pfeiffer, and A. Lau, Appl. Phys. B 63, 641–647 (1996).
[Crossref]

1995 (2)

B. Gorman and S. R. Marder, Chem. Mater. 7, 215–220 (1995).
[Crossref]

T. Johr, W. Werncke, M. Pfeiffer, A. Lau, and L. Dähne, Chem. Phys. Lett. 246, 521–526 (1995).
[Crossref]

1994 (2)

F. Meyers, S. R. Marder, B. M. Pierce, and J. L. Bredas, J. Am. Chem. Soc. 116, 10703–10714 (1994).
[Crossref]

J. L. Bredas, C. Adant, P. Tackx, and A. Persoons, Chem. Rev. 94, 243–278 (1994).
[Crossref]

1993 (2)

S. R. Marder, J. W. Perry, G. Bourhill, B. G. Tiemann, and K. Masuor, Science 261, 186–189 (1993).
[Crossref] [PubMed]

I. D. I. Albert, P. K. Das, and S. Ramesesha, J. Opt. Soc. Am. B 10, 1365–1371 (1993).
[Crossref]

1992 (2)

C. W. Dirk, L. T. Cheng, and M. G. Kuzyk, Mater. Soc. Res. Symp. Proc. 247, 73–78 (1992).
[Crossref]

W. Werncke, M. Pfeiffer, and A. Lau, Synth. Met. 51, 153–159 (1992).
[Crossref]

1991 (1)

C. Kuhn, Synth. Met. 41–43, 3681–3688 (1991).
[Crossref]

1990 (3)

A. Lau, W. Werncke, and M. Pfeiffer, Spectrochim. Acta Rev. 13, 191–223 (1990).

L. M. Tolbert and M. E. Ogle, J. Am. Chem. Soc. 112, 9519–9527 (1990).
[Crossref]

S. Matsumoto, K. Kubodera, T. Kurihara, and T. Kaino, Opt. Commun. 76, 147–152 (1990).
[Crossref]

1988 (1)

S. H. Stevenson, D. S. Donald, and G. R. Meridith, Mater. Res. Soc. Symp. Proc. 109, 103–108 (1988).
[Crossref]

1986 (2)

G. Heilig and W. Lüttgke, Chem. Ber. 119, 3102–3108 (1986);Chem. Ber. 121, 407–410 (1988).
[Crossref]

M. Pfeiffer, A. Lau, and W. Werncke, J. Raman Spectrosc. 17, 425–430 (1986).
[Crossref]

1985 (2)

F. Kajzar and J. Messier, Phys. Rev. A 32, 2352–2363 (1985).
[Crossref] [PubMed]

H. Sixl and R. Warta, Chem. Phys. Lett. 116, 307–311 (1985).
[Crossref]

1979 (3)

S. C. Mehendale and K. C. Rustagi, Opt. Commun. 28, 359–362 (1979).
[Crossref]

J. Dale, R. G. Lichtenthaler, and G. Teien, Acta Chem. Scand. B 33, 141–147 (1979).
[Crossref]

J. W. Fleming and C. S. Johnson, J. Raman Spectrosc. 8, 284–290 (1979).
[Crossref]

1977 (2)

R. W. Hellwarth, Prog. Quantum Electron. 5, 1–66 (1977).
[Crossref]

R. T. Lynch and H. Lotem, J. Chem. Phys. 66, 1905–1913 (1977).
[Crossref]

1976 (1)

W. Grahn, Tetrahedron 32, 1931–1939 (1976).
[Crossref]

1974 (3)

R. Radeglia, E. Gey, Th. Steiger, S. Kulpe, R. Lück, M. Rutheneberg, M. Stierl, and S. Dähne, J. Prakt. Chem. 316, 722–766 (1974).

J. P. Hermann and J. Ducuing, J. Appl. Phys. 45, 5100–5102 (1974).
[Crossref]

K. C. Rustagi and J. Ducuing, Opt. Commun. 10, 258–261 (1974).
[Crossref]

1971 (2)

S. Dähne and R. Radeglia, Tetrahedron 27, 3673–3693 (1971).
[Crossref]

D. R. Salahub and C. Sandorfy, Chem. Phys. Lett. 8, 71–74 (1971).
[Crossref]

1967 (1)

H. E. Nikolajewski, S. Dähne, and B. Hirsch, Chem. Ber. 100, 2616–2619 (1967).
[Crossref]

1960 (1)

S. S. Malhotra and M. C. Whiting, J. Chem. Soc. (London) 82, 3812–3822 (1960).

1958 (1)

H. Kuhn, Fortsch. Chem. Org. Naturst. 16, 169–205 (1958); Fortsch. Chem. Org. Naturst. 17, 404–451 (1959).

1925 (1)

W. König, Angew. Chem. 38, 743–748 (1925).
[Crossref]

Adant, C.

J. L. Bredas, C. Adant, P. Tackx, and A. Persoons, Chem. Rev. 94, 243–278 (1994).
[Crossref]

Albert, I. D. I.

Berlin, L.

L. Berlin and O. Riester, in Houben-Weyl: Methoden der Organischen Chemie, “Offenkettige und cyclische Polyene en-ine,” 4th ed., E. Müller, ed. (Georg Thieme Verlag, Stuttgart, 1972), Vol. V/1d, pp. 234–237.

Bourhill, G.

S. R. Marder, J. W. Perry, G. Bourhill, B. G. Tiemann, and K. Masuor, Science 261, 186–189 (1993).
[Crossref] [PubMed]

Bredas, J. L.

F. Meyers, S. R. Marder, B. M. Pierce, and J. L. Bredas, J. Am. Chem. Soc. 116, 10703–10714 (1994).
[Crossref]

J. L. Bredas, C. Adant, P. Tackx, and A. Persoons, Chem. Rev. 94, 243–278 (1994).
[Crossref]

Brooker, L. S. G.

L. S. G. Brooker, Eastman Kodak Company, Rochester, N.Y. 14550 (personal communication to Chr. Reichardt, University of Marburg, Marburg, Germany, 1971).

L. S. G. Brooker, “Azamerocyanine dyes and photographic emulsions sensitized therewith,” U.S. patent2,976,151 (21March1961); Belgium patent587,287 (29Feb.1960); Chem. Abstr. 55, 2320–2322 (1961).

Cheng, L. T.

C. W. Dirk, L. T. Cheng, and M. G. Kuzyk, Mater. Soc. Res. Symp. Proc. 247, 73–78 (1992).
[Crossref]

Dähne, L.

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

T. W. Johr, W. Werncke, L. Dähne, M. Pfeiffer, and A. Lau, Appl. Phys. B 63, 641–647 (1996).
[Crossref]

T. Johr, W. Werncke, M. Pfeiffer, A. Lau, and L. Dähne, Chem. Phys. Lett. 246, 521–526 (1995).
[Crossref]

Dähne, S.

R. Radeglia, E. Gey, Th. Steiger, S. Kulpe, R. Lück, M. Rutheneberg, M. Stierl, and S. Dähne, J. Prakt. Chem. 316, 722–766 (1974).

S. Dähne and R. Radeglia, Tetrahedron 27, 3673–3693 (1971).
[Crossref]

H. E. Nikolajewski, S. Dähne, and B. Hirsch, Chem. Ber. 100, 2616–2619 (1967).
[Crossref]

Dale, J.

J. Dale, R. G. Lichtenthaler, and G. Teien, Acta Chem. Scand. B 33, 141–147 (1979).
[Crossref]

Das, P. K.

Dirk, C. W.

C. W. Dirk, L. T. Cheng, and M. G. Kuzyk, Mater. Soc. Res. Symp. Proc. 247, 73–78 (1992).
[Crossref]

Donald, D. S.

S. H. Stevenson, D. S. Donald, and G. R. Meridith, Mater. Res. Soc. Symp. Proc. 109, 103–108 (1988).
[Crossref]

Ducuing, J.

J. P. Hermann and J. Ducuing, J. Appl. Phys. 45, 5100–5102 (1974).
[Crossref]

K. C. Rustagi and J. Ducuing, Opt. Commun. 10, 258–261 (1974).
[Crossref]

Fleming, J. W.

J. W. Fleming and C. S. Johnson, J. Raman Spectrosc. 8, 284–290 (1979).
[Crossref]

Freyer, W.

M. Pfeiffer, W. Werncke, A. Lau, and W. Freyer, in Electronic Properties of Polymers, H. Kuzmany, M. Mehring, and S. Roth, eds., Vol. 107 of Springer Series in Solid State Sciences (Springer-Verlag, Berlin, 1992), pp. 150–156.
[Crossref]

Gey, E.

R. Radeglia, E. Gey, Th. Steiger, S. Kulpe, R. Lück, M. Rutheneberg, M. Stierl, and S. Dähne, J. Prakt. Chem. 316, 722–766 (1974).

Gorman, B.

B. Gorman and S. R. Marder, Chem. Mater. 7, 215–220 (1995).
[Crossref]

Grahn, W.

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, and H.-H. Johannes, Chem. Phys. Lett. 266, 99–106 (1996).
[Crossref]

W. Grahn, Tetrahedron 32, 1931–1939 (1976).
[Crossref]

Heilig, G.

G. Heilig and W. Lüttgke, Chem. Ber. 119, 3102–3108 (1986);Chem. Ber. 121, 407–410 (1988).
[Crossref]

Hellwarth, R. W.

R. W. Hellwarth, Prog. Quantum Electron. 5, 1–66 (1977).
[Crossref]

Hermann, J. P.

J. P. Hermann and J. Ducuing, J. Appl. Phys. 45, 5100–5102 (1974).
[Crossref]

Hirsch, B.

H. E. Nikolajewski, S. Dähne, and B. Hirsch, Chem. Ber. 100, 2616–2619 (1967).
[Crossref]

Johannes, H.-H.

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, and H.-H. Johannes, Chem. Phys. Lett. 266, 99–106 (1996).
[Crossref]

Johnson, C. S.

J. W. Fleming and C. S. Johnson, J. Raman Spectrosc. 8, 284–290 (1979).
[Crossref]

Johr, T.

T. Johr, W. Werncke, M. Pfeiffer, A. Lau, and L. Dähne, Chem. Phys. Lett. 246, 521–526 (1995).
[Crossref]

Johr, T. W.

T. W. Johr, W. Werncke, L. Dähne, M. Pfeiffer, and A. Lau, Appl. Phys. B 63, 641–647 (1996).
[Crossref]

Kaino, T.

S. Matsumoto, K. Kubodera, T. Kurihara, and T. Kaino, Opt. Commun. 76, 147–152 (1990).
[Crossref]

Kajzar, F.

F. Kajzar and J. Messier, Phys. Rev. A 32, 2352–2363 (1985).
[Crossref] [PubMed]

Kendall, J. D.

J. D. Kendall, “Production of dyes of the cyanine type,” U.S. patent2,080,049 (11May1937); Chem. Abstr. 31, 4829–4830 (1937).

König, W.

W. König, Angew. Chem. 38, 743–748 (1925).
[Crossref]

Kubodera, K.

S. Matsumoto, K. Kubodera, T. Kurihara, and T. Kaino, Opt. Commun. 76, 147–152 (1990).
[Crossref]

Kuhn, C.

C. Kuhn, Synth. Met. 41–43, 3681–3688 (1991).
[Crossref]

Kuhn, H.

H. Kuhn, Fortsch. Chem. Org. Naturst. 16, 169–205 (1958); Fortsch. Chem. Org. Naturst. 17, 404–451 (1959).

Kulpe, S.

R. Radeglia, E. Gey, Th. Steiger, S. Kulpe, R. Lück, M. Rutheneberg, M. Stierl, and S. Dähne, J. Prakt. Chem. 316, 722–766 (1974).

Kurihara, T.

S. Matsumoto, K. Kubodera, T. Kurihara, and T. Kaino, Opt. Commun. 76, 147–152 (1990).
[Crossref]

Kuzyk, M. G.

C. W. Dirk, L. T. Cheng, and M. G. Kuzyk, Mater. Soc. Res. Symp. Proc. 247, 73–78 (1992).
[Crossref]

Lau, A.

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

T. W. Johr, W. Werncke, L. Dähne, M. Pfeiffer, and A. Lau, Appl. Phys. B 63, 641–647 (1996).
[Crossref]

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, and H.-H. Johannes, Chem. Phys. Lett. 266, 99–106 (1996).
[Crossref]

T. Johr, W. Werncke, M. Pfeiffer, A. Lau, and L. Dähne, Chem. Phys. Lett. 246, 521–526 (1995).
[Crossref]

W. Werncke, M. Pfeiffer, and A. Lau, Synth. Met. 51, 153–159 (1992).
[Crossref]

A. Lau, W. Werncke, and M. Pfeiffer, Spectrochim. Acta Rev. 13, 191–223 (1990).

M. Pfeiffer, A. Lau, and W. Werncke, J. Raman Spectrosc. 17, 425–430 (1986).
[Crossref]

M. Pfeiffer, W. Werncke, A. Lau, and W. Freyer, in Electronic Properties of Polymers, H. Kuzmany, M. Mehring, and S. Roth, eds., Vol. 107 of Springer Series in Solid State Sciences (Springer-Verlag, Berlin, 1992), pp. 150–156.
[Crossref]

Lichtenthaler, R. G.

J. Dale, R. G. Lichtenthaler, and G. Teien, Acta Chem. Scand. B 33, 141–147 (1979).
[Crossref]

Lotem, H.

R. T. Lynch and H. Lotem, J. Chem. Phys. 66, 1905–1913 (1977).
[Crossref]

Lück, R.

R. Radeglia, E. Gey, Th. Steiger, S. Kulpe, R. Lück, M. Rutheneberg, M. Stierl, and S. Dähne, J. Prakt. Chem. 316, 722–766 (1974).

Lüttgke, W.

G. Heilig and W. Lüttgke, Chem. Ber. 119, 3102–3108 (1986);Chem. Ber. 121, 407–410 (1988).
[Crossref]

Lynch, R. T.

R. T. Lynch and H. Lotem, J. Chem. Phys. 66, 1905–1913 (1977).
[Crossref]

Malhotra, S. S.

S. S. Malhotra and M. C. Whiting, J. Chem. Soc. (London) 82, 3812–3822 (1960).

Marder, S. R.

B. Gorman and S. R. Marder, Chem. Mater. 7, 215–220 (1995).
[Crossref]

F. Meyers, S. R. Marder, B. M. Pierce, and J. L. Bredas, J. Am. Chem. Soc. 116, 10703–10714 (1994).
[Crossref]

S. R. Marder, J. W. Perry, G. Bourhill, B. G. Tiemann, and K. Masuor, Science 261, 186–189 (1993).
[Crossref] [PubMed]

Masuor, K.

S. R. Marder, J. W. Perry, G. Bourhill, B. G. Tiemann, and K. Masuor, Science 261, 186–189 (1993).
[Crossref] [PubMed]

Matsumoto, S.

S. Matsumoto, K. Kubodera, T. Kurihara, and T. Kaino, Opt. Commun. 76, 147–152 (1990).
[Crossref]

Mehendale, S. C.

S. C. Mehendale and K. C. Rustagi, Opt. Commun. 28, 359–362 (1979).
[Crossref]

Meridith, G. R.

S. H. Stevenson, D. S. Donald, and G. R. Meridith, Mater. Res. Soc. Symp. Proc. 109, 103–108 (1988).
[Crossref]

Messier, J.

F. Kajzar and J. Messier, Phys. Rev. A 32, 2352–2363 (1985).
[Crossref] [PubMed]

Meyers, F.

F. Meyers, S. R. Marder, B. M. Pierce, and J. L. Bredas, J. Am. Chem. Soc. 116, 10703–10714 (1994).
[Crossref]

Nikolajewski, H. E.

H. E. Nikolajewski, S. Dähne, and B. Hirsch, Chem. Ber. 100, 2616–2619 (1967).
[Crossref]

Ogle, M. E.

L. M. Tolbert and M. E. Ogle, J. Am. Chem. Soc. 112, 9519–9527 (1990).
[Crossref]

Perry, J. W.

S. R. Marder, J. W. Perry, G. Bourhill, B. G. Tiemann, and K. Masuor, Science 261, 186–189 (1993).
[Crossref] [PubMed]

Persoons, A.

J. L. Bredas, C. Adant, P. Tackx, and A. Persoons, Chem. Rev. 94, 243–278 (1994).
[Crossref]

Pfeiffer, M.

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, H.-H. Johannes, and L. Dähne, Chem. Phys. 216, 337–347 (1997).
[Crossref]

T. W. Johr, W. Werncke, L. Dähne, M. Pfeiffer, and A. Lau, Appl. Phys. B 63, 641–647 (1996).
[Crossref]

W. Werncke, M. Pfeiffer, A. Lau, W. Grahn, and H.-H. Johannes, Chem. Phys. Lett. 266, 99–106 (1996).
[Crossref]

T. Johr, W. Werncke, M. Pfeiffer, A. Lau, and L. Dähne, Chem. Phys. Lett. 246, 521–526 (1995).
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[Crossref]

M. Pfeiffer, W. Werncke, A. Lau, and W. Freyer, in Electronic Properties of Polymers, H. Kuzmany, M. Mehring, and S. Roth, eds., Vol. 107 of Springer Series in Solid State Sciences (Springer-Verlag, Berlin, 1992), pp. 150–156.
[Crossref]

W. P. Su, in Solitons in Polyacetylene: A Review, T. J. Skotheim, ed., Vol. II of Handbook of Conducting Polymers (Dekker, New York, 1986), pp. 757–794.

Y. R. Shen, The Principles of Nonlinear Optics (Wiley, New York, 1984).

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Figures (4)

Fig. 1
Fig. 1

Structures of I, bis(dimethylamino)methine; II, thiacyanine dyes; and III–V, meso-azathiacyanine dyes.

Fig. 2
Fig. 2

Dependence of the real part Re γ(ω1)/γTFE and of the imaginary part Im γ(ω1)/γTFE of the third-order hyperpolarizability of thiacyanine (thiatrimethine), bis-(3-ethyl-benzothiazol-2-yl)-monomethinium tetrafluoroborate, on excitation frequency ω1 and excitation wavelength λ1, respectively, normalized to the hyperpolarizability of the solvent TFE. The molecular structure is given in the inset. Parameters of the fits (dotted curve) are γSTATI=-12γTFE, γSTATII=+3γTFE, ωTP=36 800 cm-1, ΓTP=2500 cm-1, and ωOP=23 800 cm-1.

Fig. 3
Fig. 3

Dependence of the real part Re γ(ω1)/γTFE and of the imaginary part Im γ(ω1)/γTFE of the third-order hyperpolarizability of meso-azathiacyanine (azathiatrimethine), bis-(3-ethyl-benzothiazol-2-yl)-azamonomethinium tetrafluoroborate, on excitation frequency ω1 and excitation wavelength λ1, respectively, normalized to the hyperpolarizability of the solvent TFE. The molecular structure is given in the inset. Parameters of the fits (dotted curve) are γSTATI=+5γTFE, γSTATII=+2γTFE, ωTP=38 700 cm-1, ΓTP=2500 cm-1, and ωOP=26 600 cm-1.

Fig. 4
Fig. 4

Dependence of the π-electron contribution of the static hyperpolarizabilities -γSTATπ of the homologous series of thiacyanines and of bis(dimethylamino)methines on the number of π electrons of the chain obtained from experimental results and calculated on the basis of the mopac-pm3 program package. The straight lines represent rough approximations of experimental and calculated γSTATπ by power-law dependences γπ-Nx.

Tables (2)

Tables Icon

Table 1 Absorption Maxima (λOP), Extinction Coefficients (εmax), and Oscillator Strengths (f ) of the Lowest One-Photon-Allowed Transitions of Thiacyanines, meso-Azathiacyanines, and the bis(Dimethylamino)methine Dyes a

Tables Icon

Table 2 Experimental and Calculated Third-Order Hyperpolarizabilities of the Homologous Series of Thiacyanines, meso-Azathiacyanines, and bis(Dimethylamino)methine Dyes a

Equations (2)

Equations on this page are rendered with MathJax. Learn more.

γ(ω1)
γSTATIωOP2(ωOP-ω1,2+iΓOP)(ωOP-ω3+iΓOP)+γSTATIIωOP2(ωOP-ω1+iΓOP)(ωOP-ω3+iΓOP)×ωTPωTP-2ω1+iΓTP.

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