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Organometallic Near Infrared Dyes

Previous work from the Organic and Organometallic Chemistry Group has been concerned with the preparation of organic nonlinear optical materials. Certain of these with ferrocenyl substituents were observed to have substantial first hyperpolarisability values and also to have significant absorption in the near infrared (NIR) region. NIR dyes.¹
Current interest in NIR absorbing dyes arises from their many potential applications such as:

Fluorescence sensing applications for effective, fast and accurate routine analysis of biological samples. Few species in a biological sample matrix fluoresce in the NIR, thereby reducing their interference. Applications include on-line fibre-optic biosensors, DNA sequencing, DNA chips, protein detection, immunoassays etc. This has particular importance in in vivo applications where the concentration of potentially toxic diagnostic reagents can be minimised.

Detection and treatment of cancer. A non-invasive imaging technology allows the detection of tumours using NIR optical spectroscopy and molecular tumour recognition techniques while photodynamic therapy involves the activation of prelocalised chemicals with light. NIR dyes act as photosensitisers and thereby effect the conversion of oxygen to the reactive singlet state.
In analytical chemistry, NIR dyes find potential applications as pH detectors, as well as detectors of metal ions, anions, and environmental pollutants.
Applications in optical recording, thermal displays, xerography, laser printers, laser filters, etc.

The increasing demand of NIR dyes in many different fields makes further active research towards more efficient and economical materials highly desirable. With our experience in main-group organometallic chemistry as a starting point we are now developing the chemistry of ferrocene-based NIR dyes and intend in future work to combine this also with our activities in dendrimer chemistry.

References

1. C. Arbez-Gindre, C.G. Screttas, C. Fiorini, C. Schmidt and J-M. Nunzi, Tetrahedron Lett., 1999, 40, 7413; B. Paci, C. Schmidt, C. Fiorini, J-M. Nunzi, C. Arbez-Gindre, C.G. Screttas, J. Chem. Phys. 1999, 111, 7486; S.R. Bayly, E.R. Humphrey, H. de Chair, C.G. Paredes, Z.R. Bell, J.C. Jeffery, J.A. McCleverty, M.D. Ward, F. Totti, D. Gatteschi, S. Courric, B.R. Steele and C.G.Screttas, J. Chem. Soc. Dalton Trans. 2001, 1401. C. Arbez-Gindre, B.R. Steele, G.A. Heropoulos, C.G. Screttas, J.-E. Communal, W.J. Blau and I. Ledoux-Rak, J. Organomet. Chem. 2005, 690, 1620. C. Villalonga-Barber, B.R. Steele, V. Kovac, M. Micha-Screttas and C.G. Screttas, J. Organomet. Chem. 2006, 691 , 2785-2792.

Last Update: 17.10.2006