Ethenyl-substituted dipyrrometheneboron difluoride dyes and thei

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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Other Related Categories

548405, C07D20956

Type

Patent

Status

active

Patent number

051872889

Description

ABSTRACT:
This invention relates to ethenyl-substituted derivatives of dipyrrometheneboron difluoride dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are electrically neutral, highly photostable and, in most cases, highly fluorescent with relatively narrow absorption and emission spectra. The ethenyl-substituted dyes generally have the structure: ##STR1## wherein at least one of the fluorophore substituents R.sub.1 -R.sub.7, is an ethenyl group of the formula --CX.sub.m .dbd.CY.sub.m --Z.sub.m, where m is any combination of locations 1, 2, 3, 4, 5, 6, and 7 corresponding to the location of parent fluorophore substituents R.sub.1-7. The initial ethenyl substituents X.sub.m, Y.sub.m, and Z.sub.m, which may be the same or different, are halogen, alkyl (containing 1-10 carbon atoms), cyano, ester, amide, ethenyl or polyethenyl, aryl or heteroaryl. The non-ethenyl substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-18 carbon atoms), aryl, arylalkyl, heteroaryl, acyl or sulfo.

REFERENCES:
patent: 4774339 (1988-09-01), Haugland et al.
patent: 4916711 (1990-04-01), Boyer et al.
Treibs & Kreuzer Difluorboryl-komplexe von di-und tripyrrylmethenen, Liebigs Annalen Chem. 718, 203 (1968).
Worries, et al. A novel water-soluble fluorescent probe:Synthesis, luminescence and biological properties of the sodium salt of the 4-sulfonato-3,3',5,5'-tetramethyl-2,2'-pyrromethen-1,1'-BF.sub.2 complex, Recl. Trav. Chim. Pays-Bas 104, 288 (1985).
Pavlopoulos, et al., Laser action from a tetramethylpyrromethene-BF.sub.2 complex, App. Optics 27, 4998 (1988).
Demas, J. N. & Crosby G. A. The Measurement of Photoluminescence Quantum Yields J. Phys. Chem. 75, 991 (1971).
K. C. Nicolaou, et al. A Mild Method for the Synthesis of 2-Ketopyrroles from Carboxylic Acids Tetrahedron Letters 22, 4647 (1981).
CA 112(18):160477v Reactive . . . biopolymers Haugland et al. 1988.

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