Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates

A compound of the formula:

• ##STR18## wherein at least one of the substituents R.sub.1 -R.sub.7 ts --L.sub.m G, where G is a reactive functional group that is a carboxylic acid (--(C.dbd.O)OH), a succinimidyl ester (--(C.dbd.O)O(NC.sub.4 O.sub.2 H.sub.4)), an acyl azide (--(C.dbd.O)N.sub.3), a mixed anhydride with ethyl carbonic acid (--(C.dbd.O)O(C.dbd.O)--OC.sub.2 H.sub.5), an acid halide (--(C.dbd.O)X, where X is halide), an acrylamide (--NH(C.dbd.O)CH.dbd.CH.sub.2), an alcohol (--OH), a aldehyde (--CHO), an amine (--NH.sub.2), an azide (--N.sub.3), a haloacetamide (--NH(C.dbd.O)CH.sub.2 X, where X is halide), a halomethyl (--CH.sub.2 X, where X is halide), a sulfonyl halide (--SO.sub.2 X, where X is halide), a hydrazine (--NHNH.sub.2), an isocyanate (--NCO), an isothiocyanate (--NCS), or maleimide group (--NCH.sub.4 H.sub.2 O.sub.2), and --L.sub.m --, where m=0 or 1, is a substituted or unsubstituted alkyl (containing 1-5 carbons) or arylene group, or a linking bathochromic moiety that is an alkenylene group that is an ethenylene, dienylene, or trienylene, or is a heteroarylene;
• and
• wherein the remaining substituents R.sub.1 -R.sub.7, any of which may be the same or different, are hydrogen;
• halogen;
• alkyl (containing 1-5 carbon atoms);
• sulfo;
• arylalkyl, the alkyl portion of which contains 1-5 carbon atoms;
• or aryl which may be further substituted, one or more times, by alkyl (containing 1-5 carbon atoms), or alkoxy groups wherein the alkyl portions of such groups have less than 5 carbon atoms;
• or a separate bathochromic moiety;
• or combinations thereof;
• such that at least one of the substituents R.sub.1 -R.sub.7 contains a linking bathochromic or contains a separate bathochromic moiety that is attached to the compound by a single covalent bond, where said separate bathochromic moiety is an alkenyl that is an ethenyl, dienyl, or trienyl, or is a heteroaryl group,
• where said alkenyl or alkenylene group optionally contains substituents, which may be the same or different, that are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), cyano, methyl or ethyl carboxylate ester, carboxamide (--CONH.sub.2), aryl, or heteroaryl that is optionally substituted by aryl, arylalkyl, alkyl, or alkoxy groups;
• the alkyl portions of which have fewer than 5 carbons and are optionally further substituted on the alkyl portion by methyl or ethyl carboxylate ester or carboxamide (CONH.sub.2);
• and said heteroarylene or heteroaryl group optionally contains substituents, which may be the same or different, that are aryl, arylalkyl, alkyl, or alkoxy groups;
• the alkyl portions of which have fewer than 5 carbons and are optionally further substituted on the alkyl portion by methyl or ethyl carboxylate ester or carboxamide (CONH.sub.2), or heteroaryl that is optionally substituted by aryl, arylalkyl, alkyl, or alkoxy groups;
• the alkyl portions of which have fewer than 5 carbons and are optionally further substituted on the alkyl portion by methyl or ethyl carboxylate ester or carboxamide (CONH.sub.2);
• said compound having an absorption maximum at a wavelength longer than about 525 nm in methanol and a quantum yield of greater than about 0.45.