No Access

A novel route to 4-chloro-5-alkyl-phthalonitrile and phthalocyanines derived from it

Hatice Akin Dinçer

Department of Chemistry, Technical University of Istanbul, Maslak, Istanbul 34469, Turkey

Search for more papers by this author

Ahmet Gül

Department of Chemistry, Technical University of Istanbul, Maslak, Istanbul 34469, Turkey

Search for more papers by this author

, and

Makbule Burkut Koçak

Department of Chemistry, Technical University of Istanbul, Maslak, Istanbul 34469, Turkey

Corresponding author, fax: +90 212-285-6386.

Search for more papers by this author

https://doi.org/10.1142/S1088424604000544Cited by:58 (Source: Crossref)

Abstract

A new route to the synthesis of 4-chloro-5-alkyl-phthalonitrile derivatives was shown by the displacement reaction of 4,5-dichloro-phthalonitrile and diethylmalonate, a CH-acidic precursor, in the presence of K₂CO₃. Cyclotetramerization of 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxy-methyl)benzene and the metal salt without any solvent gave the corresponding metallophthalocyanines (M = Co, CuorPd). Transesterification occurred when the reaction was carried out in hexanol in the presence of DBU to obtain the metal-free derivative. Treatment of 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxy-methyl)benzene with sodium ethoxide at ambient temperature and further acidification resulted in 2,9,16,23-tetra(carboxymethyl)-3,10,17,24-tetrachloro-phthalocyaninatopalladium(II) with partial decarboxylation. Its electronic spectrum in aqueous solution indicated no appreciable change over a pH range from 7 to 12.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

C. G. Claessenset al., Monatsh. Chem. 132, 3 (2001). Web of Science, Google Scholar
D. Wöhrle, Macromol. Rapid Commun. 22, 68 (2001). Web of Science, Google Scholar
M. J. Stillman and T. Nyokong, Phthalocyanines: Properties and Applications 1, eds. C. C. Leznoff and A. B. P. Lever (VCH, New York, 1989) pp. 133–291. Google Scholar
A. W. Snow and J. R. Griffith, Macromolecules 17, 1614 (1983), DOI: 10.1021/ma00138a033. Web of Science, Google Scholar
D. R. George and A. W. Snow, J. Heterocyclic Chem. 32, 495 (1995), DOI: 10.1002/jhet.5570320219. Web of Science, Google Scholar
I. Gürol, V. Ahsen and Ö. Bekaroglu, J. Chem. Soc., Dalton Trans. 497 (1994), DOI: 10.1039/dt9940000497. Google Scholar
D. Wöhrleet al., Synthesis 194 (1993), DOI: 10.1055/s-1993-25825. Google Scholar
A. G. Gürek and Ö. Bekaroglu, Helv. Chim. Acta 77, 1616 (1994), DOI: 10.1002/hlca.19940770618. Web of Science, Google Scholar
S. B. Kahl and J. Li, Inorg. Chem. 35, 3878 (1996), DOI: 10.1021/ic9600240. Web of Science, Google Scholar
M. Koçaket al., Dyes Pigm. 45, 9 (2000), DOI: 10.1016/S0143-7208(99)00100-X. Web of Science, Google Scholar
M. K. Sener, A. Gül and M. B. Koçak, J. Porphyrins Phthalocyanines 7, 617 (2003), DOI: 10.1142/S108842460300077X. Link, Web of Science, Google Scholar
M. P. Roze, E. L. Berzin'sh and O. Y. Neiland, Zh. Org. Khim. 28, 827 (1992). Web of Science, Google Scholar
Ö. Bekaroglu, J. Porphyrins Phthalocyanines 4, 465 (2000). Link, Web of Science, Google Scholar
S. Gürsoyet al., Monatsh. Chem. 132, 813 (2001). Web of Science, Google Scholar
A. G. Gürek and Ö. Bekaroglu, J. Chem. Soc. Dalton Trans. 1419 (1994), DOI: 10.1039/dt9940001419. Google Scholar
Z. A. Bayıret al., J. Porphyrins Phthalocyanines 1, 349 (1997). Link, Web of Science, Google Scholar
G. Gümüs, A. Gül and Ö. Bekaroglu, J. Chem. Res., Synop. 430 (1994). Google Scholar
S. Dabaket al., J. Coord. Chem. 38, 287 (1996), DOI: 10.1080/00958979608024523. Web of Science, Google Scholar
S. Z. Yıldız, H. Kantekin and Y. Gök, J. Porphyrins Phthalocyanines 5, 367 (2001), DOI: 10.1002/jpp.291. Link, Web of Science, Google Scholar
Y. Gök, H. Kantekin and I. Degirmencioglu, Supramol. Chem. 15, 335 (2003). Web of Science, Google Scholar
S. Merey and Ö. Bekaroglu, J. Chem. Soc., Dalton Trans. 4503 (1999), DOI: 10.1039/a907747b. Google Scholar
S. B. Kahl and J. Li, Inorg. Chem. 35, 3878 (1996), DOI: 10.1021/ic9600240. Web of Science, Google Scholar
U. Drechsler, M. Pfaff and M. Hanack, Eur. J. Org. Chem. 3441 (1999). Web of Science, Google Scholar
N. Kobayashi and Y. Nishiyama, J. Phys. Chem. 89, 1167 (1985), DOI: 10.1021/j100253a023. Web of Science, Google Scholar
W. A. Nevinet al., J. Electroanal. Chem. 213, 217 (1986), DOI: 10.1016/0022-0728(86)80204-2. Web of Science, Google Scholar