182296-29-3Relevant academic research and scientific papers
Novel water-soluble phthalocyanines substituted with phosphonate moieties on the benzo rings
Sharman, Wesley M.,Kudrevich, Svetlana V.,Van Lier, Johan E.
, p. 5831 - 5834 (1996)
The synthesis and characterization of a series of phthalocyanine derivatives bearing phosphonate substituents directly bound to the aromatic rings of the phthalocyanine is described. These novel water-soluble phthalocyanine tetraphosphonates are of intere
Tetrakis(diethyl phosphonate), Tetrakis(ethyl phenylphosphinate)-, and Tetrakis(diphenylphosphine oxide)-Substituted Phthalocyanines
Maerkl, Gottfried,Gschwendner, Karl,Roetzer, Ingrid,Kreitmeier, Peter
, p. 825 - 844 (2007/10/03)
The title compounds 7,9, and 11 are obtained by tetramerization of diethyl (3,4-dicyanophenyl)phosphonate (5), ethyl (3,4-dicyanophenyl)phenylphosphinate (8), and 4-(diphenylphosphinyl)benzene-1,2-dicarbonitrile (10). The 31P-NMR spectra of the phthalocyanines 7,9, and 11 and of their metal complexes present five to eight signals confirming the formation of four constitutional isomers with the expected C4h, D2h, C 2v, and Cs symmetry. In the FAB-MS of the Zn, Cu, and Ni complexes of 7 and 9, the peaks of dimeric phthalocyanines are observed. By gel-permeation chromatography, the monomeric complex [Ni(7)] and a dimer [Ni(7)]2 can be separated. These dimers differ from the known phthalocyanine dimers, i.e., possibly the P(O)(OEt)2 and P(O)(Ph)(OEt) substituents in 7 and 9 are involved in complexation. The free phosphonic acid complex [Zn(12)] and [Cu(12)] are H2O-soluble. In the FAB-MS of [Zn(12)], only the peaks of the dimer are present; the ESI-MS confirms the existence of the dimer and the metal-free dimer. In the UV/VIS spectrum of [Zn(12)], the hypsochromic shift characteristic for the known type of dimers from 660-700 nm to 620-640 nm is observed. As in the FAB-MS of [Zn(12)], the free phosphinic acid complex [Zn(13)] shows only the monomer, an ESI-MS cannot be obtained for solubility problems. The UV/VIS spectrum of [Zn(13)] demonstrates the existence of the monomer as well as of the dimer.
