Infrared dyes

There are many dyes available, each of which can be used over a 20-30 nm range and which, together, cover a wavelength range from about 365 nm in the ultraviolet to about 930 nm in the near-infrared. Dye concentrations are low, typically in the range 10 mol 1 to 10 mol 1. ... 

Symmetrical, long-chain cyanine dyes for laser appHcations provide output from 680 to 980 nm (76). Although these dyes were obtained through early screening procedures, infrared dyes for other technologies use similar stmetures. A long-chain indolenine-type cyanine dye, general stmeture as in dye (34), has been described as the sensitizer in optical disk memories (77). 

FORENSIC APPLICATION OF LEUCO AND NEAR-INFRARED DYES... 

An interesting imaging probe Id that can selectively target bacteria was recently reported by Smith et al. [31] also based on a heptamethine chromophore. The probe is composed of a bacterial affinity group, which is a synthetic zinc (II) coordination complex that targets the anionic surfaces of bacterial cells and a near infrared dye. The probe allowed detection of Staphylococcus aureus in a mouse leg infection model using whole animal near-infrared fluorescence imaging. 

Berezin MY, Lee H, Akers W, Achilefu S (2007) Near infrared dyes as lifetime solvato-chromic probes for micropolarity measurements of biological systems. Biophysical J 93 2892-2899... 

Terpetschnig E, Wolfbeis OS (1998) Luminescent probes for NIR sensing applications. In Daehne S, Resch-Genger U, Wolfbeis OS (eds) Near-infrared dyes for high technology applications, NATO ASI Ser 3, vol 53. Kluwer Academic, Dordrecht (NL), pp 161-182... 

Sophianopoulos AJ, Lipowski J, Narayanan N, Patonay G (1997) Association of near-infrared dyes with bovine serum albumin. Appl Spectrosc 51 1511-1515... 

Umezawa K, Citterio D, Suzuki K (2007) A squaraine-based near-infrared dye with bright fluorescence and solvatochromic property. Chem Lett 36 1424—1425... 

Patonay G, Salon J, Sowell J, Strekowski L (2004) Noncovalent labeling of biomolecules with red and near-infrared dyes. Molecules 9 40-49... 

Scorsone E., Christie S., Persaud K.C., Simon P., Kvasnik F., Fibre-optic evanescent sensing of gaseous ammonia with two forms of a new near-infrared dye in comparison to phenol red, Sensor. Actual. B-Chem. 2003 90 37-45. 

Infrared drying, ceramics processing, 5 656 Infrared dyes, 9 500 Infrared emission spectroscopy, 23 142 Infrared inks, 14 315 Infrared lasers, 22 180 Infrared LEDs, 22 175, 176 Infrared measurements, in growing amorphous silicon, 22 130 Infrared microspectroscopy, 16 486 Infrared reflection-absorption spectroscopy (irras), 24 72, 114-116. See also IR spectra... 

Pauli J, Vag T, Haag R, Spieles M, Wenzel M, Kaiser WA, Resch-Genger U, Hilger I (2009) An in vitro characterization study of new near infrared dyes for molecular imaging. Eur J Med Chem 44 3496-3503... 

G. Li, J. Gao, X. Zhou, O. Shimelis and R.W. Giese, Handling and detection of 25 mol of near infrared dye deoxynucleotide conjugates by capillary electrophoresis with laser-induced fluorescence detection. J. Chromatogr.A, 1004 (2003) 47-50. 

J Sowell, JC Mason, L Strekowski, G Patonay. Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis. Electrophoresis 22 2512-2517, 2001. 

Myburg, A.A., D.L. Reminglon, D.M. O Malley, R.R. Sederoff, and R.W.WhetLen, High-throughput AFLP analysis using infrared dye-labeled primers and an automated DNA sequencer. Biolechniques, 2001. 30(2) 348-52, 354,356-7. 

A few years after these events, a review article by McCleverty4 in 1968 provided (in over 170 pages) the first thorough overview of this field. This review contains a multitude of details which still merits its mention as a valuable source of information on this class of compounds. Several other reviews dealing with different aspects of dithiolene chemistry have appeared in the meantime.5"11 The field has expanded in different directions, spurred by the synthesis of several structurally unique compounds and of materials of particular use in quite diverse areas such as highly conducting molecular crystals and as infrared dyes for various applications. Dithiolenes thus represent a class of materials which are not only of significance on their own, but which also find some applications in which their unique electronic properties can be employed. 

Near-Infrared Dyes with Near-Infrared Fluorescence. This type is becoming more important, particularly in biomedical applications (see Chapter 6). Phthalo-cyanines and cyanines provide this type of fluorescence. 

As in the case of the 1,4-naphthoquinones, there has been considerable interest in developing near-infrared dyes of this class. The dye 22 [100012-51-9] is essentially the 1,5-quinone analogue of 16 (X = S) and shows a long-wavelength peak at 750 nm in trichloromethane (cmax 32000 L mol 1 cm ) [30], Thus, although 22 has the same molecular mass as 16 (X = S), it is both more bathochro-mic and more intensely absorbing. 

Fenn JB, Mann M, Meng CK Electrospray ionization for mass spectrometry of large biomolecules. Science (1989) 246 64-71. Patrick JS, Lagu AL Review applications of capillary electrophoresis to the analysis of biotechnology-derived therapeutic proteins. Electrophoresis (2001) 22 4179-4196. Sowell J, Salon J, Strekowski L, et al Covalent and noncovalent labeling schemes for near-infrared dyes in capillary electrophoresis protein applications. Methods Mol. Biol. (2004) 276 39-75. Moini M Capillary electrophoresis mass spectrometry and its application to the analysis ofbiological mixtures. Anal. Bio-anal. Chem. (2002) 373 466 180. Nemunaitis J, Holmlund JT, Kraynak M, et al. Phase I evaluation of ISIS 3521, an antisense oligodeoxynucleotide to protein kinase C-a, in patients with advanced cancer./. Clin. Oncol. (1999) 17 3586-3595. De Frutos M, Cifuentes A, Diez-Masa JC Differences in capillary electrophoresis profiles of urinary and recombinant erythropoietin. Electrophoresis (2003) 24 678-680. 

Spitler, M. Parkinson, B. A. Efficient infrared dye sensitization of van der Waals surfaces of semiconductor electrodes, Langmuir 1986, 2, 549. 

The absolute frequency position of the two-photon transition is measured by comparing the infrared dye laser wavelength with an I - stabilized He-Ne reference laser at 633 nm (see Fig.2). The hey of the wavelength comparison is a nonconfocal etalon Fabry-Perot cavity (indicated as FPE in Fig.2) kept under a vacuum better than 10-6 mbar. This optical cavity is built with two silver-coated mirrors, one flat and the other spherical (R = 60 cm), in optical adhesion to a zerodur rod. Its finesse is 60 at 633 nm and 100 at 778 nm. An auxiliary He-Ne laser as well as the dye laser are mode-matched and locked to this Fabry-Perot cavity. Simultaneously the beat frequency between the auxiliary and etalon He-Ne lasers is measured by a frequency counter. 

Infrared dyes include indoleninecyanines and azulenium compounds, both of which are used in optical recording materials.46 Other examples are metal (Mn, Fe, Co, Cd, Al, Cu, Pd)-complexed phthalocyanines, quinones, quinonoids, and imminium and diiminium compounds (Fig. 13.37). 

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