Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates

Claim 1

A compound of the formula: ##STR18## wherein at least one of the substituents R 1 -R 7 ts --L m G, where G is a reactive functional group that is a carboxylic acid (--(C═O)OH), a succinimidyl ester (--(C═O)O(NC 4 O 2 H 4 )), an acyl azide (--(C═O)N 3 ), a mixed anhydride with ethyl carbonic acid (--(C═O)O(C═O)--OC 2 H 5 ), an acid halide (--(C═O)X, where X is halide), an acrylamide (--NH(C═O)CH═CH 2 ), an alcohol (--OH), a aldehyde (--CHO), an amine (--NH 2 ), an azide (--N 3 ), a haloacetamide (--NH(C═O)CH 2 X, where X is halide), a halomethyl (--CH 2 X, where X is halide), a sulfonyl halide (--SO 2 X, where X is halide), a hydrazine (--NHNH 2 ), an isocyanate (--NCO), an isothiocyanate (--NCS), or maleimide group (--NCH 4 H 2 O 2 ), and --L 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 1 -R 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 1 -R 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 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 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 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 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.