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Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation

D. D. DOMINGUEZ

Chemistry Division, Naval Research Laboratory, Washington, DC 20375, USA

Corresponding author, Chemistry Division, Naval Research Laboratory, Washington, DC 20375, USA.

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A. W. SNOW

Chemistry Division, Naval Research Laboratory, Washington, DC 20375, USA

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J. S. SHIRK

Optical Sciences Division, Naval Research Laboratory, Washington, DC 20375, USA

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, and

R. G. S. PONG

Optical Sciences Division, Naval Research Laboratory, Washington, DC 20375, USA

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https://doi.org/10.1002/jpp.365Cited by:105 (Source: Crossref)

Abstract

The synthesis and characterization of a soluble metal-free polyethyleneoxide-capped phthalocyanine and the corresponding lead compound are described. This phthalocyanine was designed to allow the formation of dimers but to inhibit formation of higher aggregates. The monomer/dimer equilibrium constant in chloroform solutions is 750 ± 20 l mol^-1. No evidence for higher aggregates was found. The molecular extinction coefficient of the metal-free polyethyleneoxide-capped phthalocyanine in chloroform is one of the lowest known (2.5 × 104 l mol^-1cm^-1). The lead-substituted material was demonstrated to be a reverse saturable absorber from 532 nm to about 610 nm. It possesses a large nonlinear absorption coefficient in the visible and is a promising optical limiter material.

This article is a U.S. Government work and is in the public domain in the U.S.A.

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References

J. S. Shirk, Phthalocyanines: Properties and Applications 4, eds. C. C. Leznoff and A. B. P. Lever (VCH, New York, 1996) pp. 79–181. Google Scholar
A. W. Snow and N. L. Jarvis, J. Am. Chem. Soc. 106, 4706 (1984), DOI: 10.1021/ja00329a012. Crossref, Web of Science, Google Scholar
R. Sankar, P. Vasudevan and N. K. Jha, Synth. React. Inorg. Met.-Org. Chem. 27, 1277 (1997). Crossref, Web of Science, Google Scholar
J. S. Shirket al., Appl. Phys. Lett. 63, 1880 (1993), DOI: 10.1063/1.110635. Crossref, Web of Science, Google Scholar
J. S. Shirket al., Appl. Phys. Lett. 55, 1287 (1989), DOI: 10.1063/1.101634. Crossref, Web of Science, Google Scholar
J. S. Shirket al., J. Phys. Chem. A 104, 1438 (2000), DOI: 10.1021/jp993254j. Crossref, Web of Science, Google Scholar
T. M. Keller, T. R. Price and J. R. Griffith, Synthesis 613 (1980), DOI: 10.1055/s-1980-29135. Google Scholar
C. C. Leznoff and T. W. Hall, Tetrahedron Lett. 23, 3023 (1982), DOI: 10.1016/S0040-4039(00)87523-1. Crossref, Web of Science, Google Scholar
A. W. Snow, J. R. Griffith and N. P. Marullo, Macromolecules 17, 1614 (1984), DOI: 10.1021/ma00138a033. Crossref, Web of Science, Google Scholar
C. C. Leznoffet al., Can. J. Chem. 63, 623 (1985), DOI: 10.1139/v85-102. Crossref, Web of Science, Google Scholar
C. C. Leznoff and A. B. P. Lever (eds.) , Phthalocyanines: Properties and Applications ( VCH Publishers , New York , 1996 ) . Google Scholar
N. B. McKeown and J. Painter, J. Mater. Chem. 4, 1153 (1994), DOI: 10.1039/jm9940401153. Crossref, Web of Science, Google Scholar
R. Shankaret al., Indian J. Chem. 35B, 894 (1996). Google Scholar
P. A. Barrett, D. A. Frye and R. P. Linstead, J. Chem. Soc. 1157 (1938), DOI: 10.1039/jr9380001157. Web of Science, Google Scholar
A. W. Snow, J. S. Shirk and R. G. S. Pong, J. Porphyrins Phthalocyanines 4, 518 (2000). Link, Web of Science, Google Scholar
M. Sommerauer, C. Rager and M. Hanack, J. Am. Chem. Soc. 118, 10085 (1996), DOI: 10.1021/ja961009x. Crossref, Web of Science, Google Scholar
R. D. Georgeet al., J. Porphyrins Phthalocyanines 2, 1 (1998). Link, Web of Science, Google Scholar
E. A. Derkacheva Luk'yanets, J. Gen. Chem. USSR 50, 1874 (1980). Web of Science, Google Scholar
O. E. Sielckenet al., J. Am. Chem. Soc. 109, 4261 (1987), DOI: 10.1021/ja00248a021. Crossref, Web of Science, Google Scholar
S. Foleyet al., J. Chem. Soc., Perkin Trans. 2, 1725 (1997). Google Scholar
N. Kobayashi and A. B. P. Lever, J. Am. Chem. Soc. 109, 4261 (1987). Web of Science, Google Scholar
S. A. Mikhalenkoet al., J. Gen. Chem. USSR 41, 2770 (1971). Web of Science, Google Scholar
C. C. Leznoffet al., Photochem. Photobiol. 49, 279 (1989), DOI: 10.1111/j.1751-1097.1989.tb04107.x. Crossref, Web of Science, Google Scholar
S. A. Mikhalenko and E. A. Luk'yanets, J. Gen. Chem. USSR 39, 2081 (1969). Web of Science, Google Scholar
C. Piechocki and J. Simon, J. Nouv. J. Chim. 9, 159 (1985). Web of Science, Google Scholar
W. J. Schutte, M. Sluyters-Rehbach and J. H. Sluyters, J. Phys. Chem. 97, 6069 (1993), DOI: 10.1021/j100124a047. Crossref, Web of Science, Google Scholar
S. R. Flomet al., Proc. Mater. Res. Soc. 247, 271 (1992). Crossref, Web of Science, Google Scholar