Long wavelength heteroaryl-substituted dipyrrometheneboron diflu

Details Long wavelength heteroaryl-substituted dipyrrometheneboron diflu Long wavelength heteroaryl-substituted dipyrrometheneboron diflu

1990-12-18

1993-09-28

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2523017, 372 39, 372 53, 372 54, 548405, 544229, C07D20956, C07D20900, H01S 3213

Patent

active

052487822

ABSTRACT:
This invention describes novel 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes containing heteroaryl substituents conjugated to the fluorophore and methods for their synthesis. The heteroaryl substituted compounds (heteroaryl dyes) generally have the structure: ##STR1## wherein any or all of the substituents R.sub.1 -R.sub.7, but at least one of such substituents, is a heteroaryl group, including 5- or 6-member rings, singly or fused, containing one or more heteroatoms. The new dyes that have spectral properties that are significantly shifted from those of the parent alkyl-substituted dyes, usually accompanied by an increase in photostability and in some cases by an increase in the extinction coefficient relative to the alkyl-substituted dyes. The general method of synthesis includes formation of pyrromethene salt intermediates followed by cyclization with boron trifluoride in the presence of a base to give heteroaryl-substituted dipyrrometheneboron difluoride dyes.

REFERENCES:
patent: 3733334 (1973-05-01), Padmanathan I
patent: 3769300 (1973-10-01), Padmanathan II
patent: 4774339 (1988-09-01), Haugland et al.
patent: 4839260 (1989-06-01), Logan I
patent: 4839274 (1989-06-01), Logan II
patent: 4916711 (1990-04-01), Boyer et al.
Falk et al., Monatshefte Fur Chemie, vol. 110, pp. 987 to 1001 (1979).
Treibs & Kreuzer et al I, Difluorboryl-komplexe von di-und tripyrrylmethenen, Liebigs Annalen Chem. 718, 208-223 (1968).
Wories, 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, 288-291 (1985).
Pavlopoulos, et al., Laser action from a tetramethylpyrromethene-BF.sub.2 complex, App. Optics 27, 4998-4999 (1988).
Demas & Crosby, J. Phys. Chem. 75, 991-1024 (1971).
H. Rapoport et al., J. Am. Chem. Soc. 84, 2178-2181 (1962).
R. M. Silverstein et al., Org. Synth. Coll. vol. IV, pp. 831-833 (1970).
A. Treibs et al., II Ann. Der Chemie 739, 225-227 (1970).
C. F. H. Allen et al., Org. Synth. Coll. vol. III, pp. 358-360 (1960).
J. A. S. Cavaleiro, et al., J. Org. Chem. 53, 5847-5849 (1988).
C. G. Kruse, et al. Heterocycles 26, 3141-3151 (1987).

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