US 5,187,288 AGranted

Ethenyl-substituted dipyrrometheneboron difluoride dyes and their synthesis

AssigneeMolecular Probes, Inc.

InventorsHee C. Kang, Richard P. Haugland

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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.

Claims20

Dependent claims

A compound of the general formula:

##STR22## wherein at least one of the fluorophore substituents R.sub.1 -R.sub.7 is an initial ethenyl group having initial ethenyl substituents;
or a conjugated dienyl group having initial and secondary ethenyl substituents;
or a conjugated trienyl group having initial, secondary and tertiary ethenyl substituents, and
where said initial, secondary, and tertiary ethenyl substituents which may be the same or different, are hydrogen;
halogen;
alkyl (containing 1-10 carbon atoms);
cyano;
carboxylate ester;
carboxamide;
or aryl or heteroaryl, where said heteroaryl is pyrrole, thiophene, furan, oxazole, isoxazole, oxadiazole, imidazole, benzoxazole, benzothiazole, benzimidazole, benzofuran, or indole, which aryl or heteroaryl may be further substituted, one or more times, by alkyl (containing 1-5 carbon atoms), or alkoxy groups the alkyl portions of which groups have less than 5 carbon atoms, or combinations thereof;
and
the remaining fluorophore substituents R.sub.1 -R.sub.7 that are non-ethenyl, -dienyl, or -trienyl, which may be the same or different, are hydrogen;
alkyl (containing 1-18 carbon atoms);
acyl;
sulfo;
arylalkyl, the alkyl portion of which contains 1-18 carbon atoms;
or aryl or heteroaryl, which may be further substituted, one or more times, by alkyl (containing 1-5 carbon atoms), or alkoxy or dialkylamino groups wherein the alkyl portions of such groups have less than 5 carbon atoms, or combinations thereof;
said compound having an absorption maximum at a wavelength longer than about 525 nm.

15 more elements

Dependencies are inferred from the claim text.