Thioheterocyclic near-infrared dyes

Details Thioheterocyclic near-infrared dyes Thioheterocyclic near-infrared dyes

1998-01-23

1999-08-03

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548120, 548152, 548215, 548217, 548251, 548255, 5482632, 5483001, 548518, 5462697, 5462714, 5462727, 544298, C07D27704, C07D29310, C07D41300, C07D23902

Patent

active

059327405

ABSTRACT:
Disclosed is a novel near-infrared absorbing dye of formula: ##STR1## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;
n is an integer of 2 or 3;
R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;
R.sup.3 represents a ring chosen from a set consisting of aryl, substituted aryl, and a heterocyclic ring of a type present in photographic emulsions;
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together can represent atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;
R.sup.8, R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, or substituted aryl of 6-10 carbons; and
R.sup.10 represents an alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, or substituted aryl of 6-10 carbons;
with the proviso that when R.sup.3 is phenyl or substituted phenyl and n=3, R.sup.1 or R.sup.2 is not an unsubstituted alkyl.

REFERENCES:
patent: 4882265 (1989-11-01), Langanis et al.
Slominskii et. al., "Polymethine Dyes with Hydrocarbon Bridges . . . ", Inst. Org. Chem., Acad. Sci. Ukranian SSR, vol. 22, pp. 351-356, 1979.
Slominskii, Et. Al. CA 91:22390, 1979.
L. Strekowski, et. al. Facile Derivatization of Heptamethine Cyanine Dyes, Synthetic Communication, 22(17), pp. 2593-2598, 1992.
L. Strekowski, Et. Al., Substitution Reaction of a Nucleofugal Group in Heptamethine Cyanine Dyes. Synthesis of an Isocyanato Derivative for Labeling of Protein with a Near Infrared Chromophore, J. Or. Chem. 57, pp. 4578-4580, 1992.
R. J. Williams, Et. Al, Comparison of Covalent and Non-Covalent Labeling with Near-Infrared Dyes for the High-Performance Liquid Chromatographic Determination of Human Serum Albumin, Anal. Chem., vol. 65, pp. 601-605, 1993.

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