Abstract

We report on an active tuning of nonlinear absorption from reverse saturable absorption to saturable absorption in supramolecular zinc diphenylporphyrins by the combination of molecular and supramolecular levels at 532, 542 and 552 nm. Firstly, the modifications of molecular structures with bromination result in a discrete but regular change in magnitude and sign of nonlinear absorption (NLA). Furthermore, a fine tuning of NLA was obtained by the intermolecular weak interaction of pyridine and zinc porphyrins. Using an association model, we theoretically simulate the change of NLA. Compared with modifying molecular structures of conventional organic materials, the weak intermolecular interaction of supramolecular porphyrins has another advantage that it can be realized more easily and flexibly to change NLA.

© 2006 Optical Society of America

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    [CrossRef]
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  21. S. Roy, and K. Kulshrestha, "Theoretical analysis of all-optical spatial light modulation in organometallics based on triplet state absorption dynamics," Opt. Commun. 252, 275 (2005).
    [CrossRef]
  22. M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
    [CrossRef]
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    [CrossRef] [PubMed]
  25. A. Satake, and Y. Kobuke, "Dynamic supramolecular porphyrin systems," Tetrahedron 61, 13 (2005).
    [CrossRef]
  26. H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
    [CrossRef]
  27. P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
    [CrossRef]

2005 (4)

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

S. Roy, and K. Kulshrestha, "Theoretical analysis of all-optical spatial light modulation in organometallics based on triplet state absorption dynamics," Opt. Commun. 252, 275 (2005).
[CrossRef]

A. Satake, and Y. Kobuke, "Dynamic supramolecular porphyrin systems," Tetrahedron 61, 13 (2005).
[CrossRef]

2004 (4)

Z. B. Liu, J. G. Tian, W. P. Zang, W. Y. Zhou, F. Song, C. P. Zhang, J. Y. Zheng, and H. Xu, "Flexible alteration of optical nonlinearities of iodine charge-transfer complexes in solutions," Opt. Lett. 29, 1099 (2004).
[CrossRef] [PubMed]

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

M. Calvete, G. Y. Yang, and M. Hanack, "Porphyrins and phthalocyanines as materials for optical limiting," Synth. Met. 141, 231 (2004).
[CrossRef]

2003 (3)

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

A. Karotki, M. Drobizhev, M. Kruk, C. Spangler, E. Nickel, N. Mamardashvili, and A. Rrebane, "Enhancement of two-photon absorption in tetrapyrrolic compounds," J. Opt. Soc. Am. B 20, 321 (2003).
[CrossRef]

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

2002 (2)

2000 (1)

S. M. Kuebler, R. G. Denning, H. L. Anderson, "Large third-order electronic polarizability of a conjugated porphyrin polymer," J. Am. Chem. Soc. 122, 339 (2000).
[CrossRef]

1998 (1)

W. J. Su, T. M. Cooper, and M. C. Brant, "Investigation of reverse-saturable absorption in brominated porphyrins," Chem. Mater. 10, 1212 (1998).
[CrossRef]

1996 (2)

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

1994 (1)

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

1993 (1)

P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
[CrossRef]

1992 (1)

L. W. Tutt, and A. Kost, "Optical limiting performance of C60 and C70 solutions," Nature 356, 225 (1992).
[CrossRef]

1990 (2)

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

J. M. Lehn, "Perspectives in supramolecular chemistry: from molecular recognition towards molecular information processing and self-organization," Angew. Chem. Int. Ed. Engl. 29, 1304 (1990).
[CrossRef]

1988 (1)

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

1985 (1)

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

Agullo-Lopez, F.

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

Akdas, H.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Anderson, H.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Anderson, H. L.

S. M. Kuebler, R. G. Denning, H. L. Anderson, "Large third-order electronic polarizability of a conjugated porphyrin polymer," J. Am. Chem. Soc. 122, 339 (2000).
[CrossRef]

Batista, A. A.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Bedworth, P. V.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Bhyrappa, P.

P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
[CrossRef]

Bindra, K. S.

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

Blake, I.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Blau, W.

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

Boni, L. D.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Bosshard, C.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Bourhill, G.

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Brant, M. C.

W. J. Su, T. M. Cooper, and M. C. Brant, "Investigation of reverse-saturable absorption in brominated porphyrins," Chem. Mater. 10, 1212 (1998).
[CrossRef]

Bredas, J. L.

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Byrne, H.

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

Calvete, M.

M. Calvete, G. Y. Yang, and M. Hanack, "Porphyrins and phthalocyanines as materials for optical limiting," Synth. Met. 141, 231 (2004).
[CrossRef]

Chen, C. T.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Chng, L. L.

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Cooper, T. M.

W. J. Su, T. M. Cooper, and M. C. Brant, "Investigation of reverse-saturable absorption in brominated porphyrins," Chem. Mater. 10, 1212 (1998).
[CrossRef]

de la Torre, G.

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

Denning, R. G.

S. M. Kuebler, R. G. Denning, H. L. Anderson, "Large third-order electronic polarizability of a conjugated porphyrin polymer," J. Am. Chem. Soc. 122, 339 (2000).
[CrossRef]

Dennis, W. M.

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

Desai, N. R.

Dharmadhikari, A. K.

Diederich, F.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Dinelli, L. R.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Drobizhev, M.

Fleitz, P.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Gorman, C. B.

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Gunter, P.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Hagan, D. J.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

Hanack, M.

M. Calvete, G. Y. Yang, and M. Hanack, "Porphyrins and phthalocyanines as materials for optical limiting," Synth. Met. 141, 231 (2004).
[CrossRef]

Jain, B.

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

Kamada, K.

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

Karotki, A.

Katterle, M.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Kelly, J. M.

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

Kiran, P. P.

Kobuke, Y.

A. Satake, and Y. Kobuke, "Dynamic supramolecular porphyrin systems," Tetrahedron 61, 13 (2005).
[CrossRef]

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

K. Ogawa, T. Zhang, K. Yoshihara, Y. Kobuke, "Large third-order optical nonlinearity of self-assembled porphyrin oligomers," J. Am. Chem. Soc. 124, 22 (2002).
[CrossRef] [PubMed]

Kost, A.

L. W. Tutt, and A. Kost, "Optical limiting performance of C60 and C70 solutions," Nature 356, 225 (1992).
[CrossRef]

Kramer, R.

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

Krishnan, V.

P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
[CrossRef]

Kruk, M.

Kuebler, S. M.

S. M. Kuebler, R. G. Denning, H. L. Anderson, "Large third-order electronic polarizability of a conjugated porphyrin polymer," J. Am. Chem. Soc. 122, 339 (2000).
[CrossRef]

Kulshrestha, K.

S. Roy, and K. Kulshrestha, "Theoretical analysis of all-optical spatial light modulation in organometallics based on triplet state absorption dynamics," Opt. Commun. 252, 275 (2005).
[CrossRef]

Kumar, G. R.

Lai, K. S.

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Lau, W. P.

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Lee, I. Y. S.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Lee, Y. W.

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Lehn, J. M.

J. M. Lehn, "Perspectives in supramolecular chemistry: from molecular recognition towards molecular information processing and self-organization," Angew. Chem. Int. Ed. Engl. 29, 1304 (1990).
[CrossRef]

Lewis, K.

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Liu, Z. B.

Maiya, B. G.

Mamardashvili, N.

Mansour, K.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Marder, S. R.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

McEwan, K.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

McLean, D.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Mendonca, C. R.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Meyers, F.

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Miles, P.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Misoguti, L.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Nethaji, M.

P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
[CrossRef]

Neto, N. M. B.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Ng, D.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Nickel, E.

Oak, S. M.

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

Ogawa, K.

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

K. Ogawa, T. Zhang, K. Yoshihara, Y. Kobuke, "Large third-order optical nonlinearity of self-assembled porphyrin oligomers," J. Am. Chem. Soc. 124, 22 (2002).
[CrossRef] [PubMed]

Ohashi, A.

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

Ohta, K.

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

Perry, J. W.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Pierce, B. M.

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Queiroz, S. L.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Reddy, D. R.

Rogers, J.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Roy, S.

S. Roy, and K. Kulshrestha, "Theoretical analysis of all-optical spatial light modulation in organometallics based on triplet state absorption dynamics," Opt. Commun. 252, 275 (2005).
[CrossRef]

Rrebane, A.

Said, A. A.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

Sasabe, H.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Satake, A.

A. Satake, and Y. Kobuke, "Dynamic supramolecular porphyrin systems," Tetrahedron 61, 13 (2005).
[CrossRef]

Schneider, H. J.

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

Schneider, U.

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

Schreiber, M.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Sheik-Bahae, M.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

Simova, S.

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

Singh, C. P.

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

Slagle, J.

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Song, F.

Spangler, C.

Spreiter, R.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Su, W. J.

W. J. Su, T. M. Cooper, and M. C. Brant, "Investigation of reverse-saturable absorption in brominated porphyrins," Chem. Mater. 10, 1212 (1998).
[CrossRef]

Tian, J. G.

Tian, M.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Torres, T.

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

Tutt, L. W.

L. W. Tutt, and A. Kost, "Optical limiting performance of C60 and C70 solutions," Nature 356, 225 (1992).
[CrossRef]

Tykwinski, R. R.

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

Van Stryland, E. W.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

Vazquez, P.

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

Wanda, T.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Wei, T. H.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

Wu, X. L.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

Xu, H.

Yang, G. Y.

M. Calvete, G. Y. Yang, and M. Hanack, "Porphyrins and phthalocyanines as materials for optical limiting," Synth. Met. 141, 231 (2004).
[CrossRef]

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Yoshihara, K.

K. Ogawa, T. Zhang, K. Yoshihara, Y. Kobuke, "Large third-order optical nonlinearity of self-assembled porphyrin oligomers," J. Am. Chem. Soc. 124, 22 (2002).
[CrossRef] [PubMed]

Zang, W. P.

Zhang, C. P.

Zhang, T.

K. Ogawa, T. Zhang, K. Yoshihara, Y. Kobuke, "Large third-order optical nonlinearity of self-assembled porphyrin oligomers," J. Am. Chem. Soc. 124, 22 (2002).
[CrossRef] [PubMed]

Zheng, J. Y.

Zhou, W. Y.

Zilio, S. C.

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Adv. Funct. Mater. (1)

K. McEwan, K. Lewis, G. Y. Yang, L. L. Chng, Y. W. Lee, W. P. Lau, and K. S. Lai, "Synthesis, characterization, and nonlinear optical study of metalloporphyrins," Adv. Funct. Mater. 13, 863 (2003).
[CrossRef]

Adv. Mater. (2)

C. Bosshard, R. Spreiter, P. Gunter, R. R. Tykwinski, M. Schreiber, and F. Diederich, "Structure-property relationships in nonlinear optical tetraethynylethenes," Adv. Mater. 8, 231 (1996).
[CrossRef]

K. McEwan, P. Fleitz, J. Rogers, J. Slagle, D. McLean, H. Akdas, M. Katterle, I. Blake, and H. Anderson, "Reverse saturable absorption in the near-infrared by fused porphyrin dimmers," Adv. Mater. 16, 1933 (2004).
[CrossRef]

Angew. Chem. Int. Ed. Engl. (1)

J. M. Lehn, "Perspectives in supramolecular chemistry: from molecular recognition towards molecular information processing and self-organization," Angew. Chem. Int. Ed. Engl. 29, 1304 (1990).
[CrossRef]

Appl. Opt. (1)

Chem. Mater. (1)

W. J. Su, T. M. Cooper, and M. C. Brant, "Investigation of reverse-saturable absorption in brominated porphyrins," Chem. Mater. 10, 1212 (1998).
[CrossRef]

Chem. Rev. (1)

G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, "Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds," Chem. Rev. 104, 3723 (2004).
[CrossRef] [PubMed]

IEEE J. Quantum Electron (1)

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, "Sensitive measurement of optical nonlinearities using a single beam," IEEE J. Quantum Electron 26, 760 (1990).
[CrossRef]

J. Am. Chem. Soc. (4)

H. J. Schneider, R. Kramer, S. Simova, and U. Schneider, "Solvent and salt effects on binding constants of organic substrates in macrocyclic host compounds. a general equation measuring hydrophobic binding contributions," J. Am. Chem. Soc. 110, 6442 (1988).
[CrossRef]

S. M. Kuebler, R. G. Denning, H. L. Anderson, "Large third-order electronic polarizability of a conjugated porphyrin polymer," J. Am. Chem. Soc. 122, 339 (2000).
[CrossRef]

K. Ogawa, T. Zhang, K. Yoshihara, Y. Kobuke, "Large third-order optical nonlinearity of self-assembled porphyrin oligomers," J. Am. Chem. Soc. 124, 22 (2002).
[CrossRef] [PubMed]

K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, and K. Ohta, "Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin," J. Am. Chem. Soc. 125, 13356(2003).
[CrossRef] [PubMed]

J. Chem. Soc. Dalton Trans. (1)

P. Bhyrappa, V. Krishnan, and M. Nethaji, "Solvation and axial ligation properties of (2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato)zinc(II)," J. Chem. Soc. Dalton Trans. 12, 1901 (1993).
[CrossRef]

J. Opt. Soc. Am. B (1)

J. Phys. Chem. B (1)

N. M. B. Neto, L. D. Boni, C. R. Mendonca, L. Misoguti, S. L. Queiroz, L. R. Dinelli, A. A. Batista, and S. C. Zilio, "Nonlinear absorption dynamics in tetrapyridyl metalloporphyrins," J. Phys. Chem. B 109, 17340 (2005).
[CrossRef]

Nature (1)

L. W. Tutt, and A. Kost, "Optical limiting performance of C60 and C70 solutions," Nature 356, 225 (1992).
[CrossRef]

Opt. Commun. (3)

W. Blau, H. Byrne, W. M. Dennis, and J. M. Kelly, Reverse saturable absorption in tetraphenylporphyrins.Opt. Commun. 56, 25 (1985).
[CrossRef]

C. P. Singh, K. S. Bindra, B. Jain, and S. M. Oak, "All-optical switching characteristics of metalloporphyrins," Opt. Commun. 245, 407 (2005).
[CrossRef]

S. Roy, and K. Kulshrestha, "Theoretical analysis of all-optical spatial light modulation in organometallics based on triplet state absorption dynamics," Opt. Commun. 252, 275 (2005).
[CrossRef]

Opt. Lett. (1)

Science (2)

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wanda, M. Tian, and H. Sasabe, "Organic optical limiter with a strong nonlinear absorptive response," Science 273, 1533 (1996).
[CrossRef]

.S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bredas, and B. M. Pierce, "A unified description of linear and nonlinear polarization in organic polymethine dyes," Science 256, 632 (1994).
[CrossRef]

Synth. Met. (1)

M. Calvete, G. Y. Yang, and M. Hanack, "Porphyrins and phthalocyanines as materials for optical limiting," Synth. Met. 141, 231 (2004).
[CrossRef]

Tetrahedron (1)

A. Satake, and Y. Kobuke, "Dynamic supramolecular porphyrin systems," Tetrahedron 61, 13 (2005).
[CrossRef]

Other (3)

D. S. Chemla, and J. Zyss, eds. Nonlinear Optical Properties of Organic Molecules and Crystals. (Academic Press, Orlando, FL, 1987)

P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers. (Wiley, New York 1991).

H. S. Nalwa, S. Miyata, eds. Nonlinear Optics of Organic Molecules and Polymers. (CRC Press, Boca Raton, FL, 1997).

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Figures (3)

Fig. 1.
Fig. 1.

The linear and nonlinear absorption data of ZnDPP, ZnDPPBr, and ZnDPPBr2. (a) Molecular structures and Linear absorption spectra. (b) Open-aperture Z-scan curves with 5-ns pulse duration at 532nm. Symbols represent experimental data; solid lines are theoretical fittings using a five-level model.

Fig. 2.
Fig. 2.

Change of nonlinear absorption for ZnDPP with various concentration of pyridine.(a) Open-aperture Z-scan curves of at 532nm. (b) Absorption cross-sections of ground and excited states vs [Py]0:[Por]0. The solid lines are fittings with K=0.48×104 M-1 using association model. Inset gives the equilibrium equation between zinc porphyrins and pyridine.

Fig. 3.
Fig. 3.

Spectrophotometric titrations of (a) ZnDPP, (b) ZnDPPBr, and (c) ZnDPPBr2 with pyridine. The cross section difference (σT0) of (d) ZnDPP, (e) ZnDPPBr, and (f) ZnDPPBr2 vs the concentration of pyridine [Py]0:[Por]0. The dotted lines represent σT0=0. If σT0>0, RSA will occur, and If σT0<0, SA will occur. The solid fitting curves are obtained directly from the association model.

Tables (1)

Tables Icon

Table 1. Photophysical parameters of ZnDPP, ZnDPPBr, and ZnDPPBr2

Equations (1)

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

K = [ Por∙Py ] [ Por ] [ Py ] = [ Por∙Py ] ( [ Por ] 0 [ Por∙Py ] ) ( [ Py ] 0 [ Por∙Py ] )

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