Phosphonated polypyridyl compounds and their complexes

Details Phosphonated polypyridyl compounds and their complexes Phosphonated polypyridyl compounds and their complexes

1996-10-30

1998-08-04

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546257, 546258, 546263, 5462724, 5462734, C07F 958, C07D40104, C09B 5710, H01G 920

Patent

active

057895929

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE

This application is a 371 of PCT/11394/00088 filed May 2, 1994.
The present invention relates to the synthesis of a new class of phosphonated polypyridyl compounds and complexes, which have a number of applications. For example, the metal complexes can serve as ligands to form complexes with a variety of elements, in particular transition metals. The phosphonate groups of these polypyridyl complexes provide the transition metal complex with unique and desirable properties. Thus, the specific binding of the complex to oxidic functions e.g. the surface of oxides can be achieved. The formation of such surface bonds is very important.
Transition metal-phosphonated polypyridyl ligand complexes can be used as dyestuffs. Here the phosphonate group assists in immobilizing the dyestuff at the surface of the desired substrate. Such phosphonate modified complexes can be used in numerous systems.
Of particular interest is the application of these complexes as sensitizers in photogalvanic cells. In such a system, transition metal-phosphonated polypyridyl ligand complexes can be coated onto semiconducting oxides such as TiO.sub.2. Due to the phosphonate groups, the adherence of the phosphonated polypyridyl ligand complex to the oxide surface is exceptionally strong, rendering these complexes particularly useful for the conversion of visible light into electric energy.
While the application of transition metal-phosphonated polypyridyl ligand complexes as sensitizers is of great practical importance, there are other applications (detailed later) where the exceptional properties of these polypyridyl compounds (for example in its non-metal complex form) and complexes having phosphonate binding groups can be used.
Thus, phosphonated bi- and poly- pyridyl complex can be grafted into metal surfaces to inhibit their corrosion. This is due to the formation of a chelate at the metal surface protecting the latter from attack by oxidants.
The adhesion of the phosphonate groups to matter present in living systems i.e. materials forming a bond with the skeleton of living beings such as calcium oxide, permits even more widespread applications of these ligands.
In particular these phosphonated polypyridyl ligand compounds may be used alone or in complexed form with elements such as radioactive technecium as diagnostic agents or remedies in tumoral diseases, as anticancer agents and as biosensors.
According to the invention, there is provided a bi- or polypyridyl phosphonate in metal free or metal complex form.
In particular, there is provided a compound, in metal-free or metal complex form of formula 1 to 3 ##STR2## in which R is hydrogen or C.sub.1-30 alkyl; ligand which is a compound of formula 1 to 3, as defined above.
Preferably the metal of such a metal complex is a transition metal, more preferably selected from the group consisting of Ru, Os, Fe, Re or Tc, especially Ru(II), Os(II), Fe(II), Re(I) or Tc(I), (II), (III), (IV) or (V).
Further according to the invention there is provided a metal complex of formulae 4 to 13 L.sub.h or L.sub.i ; and Br.sup.-, I.sup.-, CN.sup.-, NCO.sup.-, H.sub.2 O, P(R.sub.1).sub.3, P(R.sub.1).sub.2 (where R.sub.1 is unsubstituted C.sub.1-30 alkyl, phenyl, unsubstituted or substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halogen or pyridine, unsubstituted or substituted by one group selected from vinyl, primary, secondary and tertiary amines, OH and C.sub.1-30 alkyl); ##STR3## where R' is C.sub.1-30 alkyl or phenyl ##STR4## where each R independently is as defined above.
One aspect of the invention relates to the use of new transition metal complexes according to the invention in photovoltaic cells. These complexes can be coated on titanium dioxide films rendering the device effective in the conversion of visible light to electric energy.
Titanium dioxide films (layers) are known for their semiconductive properties and this property renders them useful for photovoltaic cells. However titanium dioxide has a large band gap; it does not absorb light in the visible region of the spect

REFERENCES:
Chemical Abstracts, vol. 122,(No. 14), abst. No. 165,412m,Apr. 3, 1995.
Chemical Abstracts, vol. 123,(No. 12), abst. No. 148,949v,Sep. 18, 1995.
Chemical Abstracts, vol. 124,(No. 18), abst. No. 237,199p,Apr. 29, 1996.

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