Rigidized monomethine cyanines
AssigneeCarnegie Mellon University
InventorsBhalchandra M. Karandikar, Alan S. Waggoner, Ratnakar B. Mujumdar
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Abstract
Boron complexes of certain bis-heterocyclic compounds are provided. The complexes resemble monomethine cyanines and are useful for imparting fluorescent properties to materials by covalent and noncovalent association. The compounds have the following general formula: ##STR1## wherein the dotted lines Z.sub.1 and Z.sub.2 represent the atoms necessary to complete a structure selected from the group consisting of one ring, two fused rings, and three fused rings, each said ring having five or six atoms, and each said ring comprising carbon atoms and, optionally, no more than two atoms selected from oxygen, nitrogen and sulfur, and R.sub.1 through R.sub.5 represent various atoms or groups and M is Cl or F.
Claims11
A fluorescent molecule having the structure ##STR49## wherein:
- X and Y are selected from the group consisting of --C(CH.sub.3).sub.2 --, oxygen, sulfur, --CH.dbd.CH--, and >N--W--K where N is nitrogen;
- dotted lines Z.sub.1 and Z.sub.2 represent the atoms necessary to complete a structure selected from the group consisting of one ring, two fused rings, and three fused rings, each said ring having five or six atoms, and each said ring comprising carbon atoms and, optionally, no more than two atoms selected from oxygen, nitrogen and sulfur;
- R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are selected from the group consisting of --K and --W--K;
- M is selected from the group consisting of F and Cl;
- W is a linker selected from the group consisting of branched alkyl chains of 1-27 carbon atoms, straight alkyl chains of 1-27 carbon atoms, monoethers containing 2-20 carbon atoms, and polyethers containing 2-20 carbon atoms;
- and
- K is a group conferring desired properties and is selected from the group consisting of:
- neutral groups that reduce water solubility selected from the group consisting of hydrogen and halogen atoms;
- polar groups that increase water solubility selected from the group consisting of amide, sulfonate, sulfate, phosphate, quaternary ammonium, hydroxyl and phosphonate;
- functional groups that can be used in labeling reactions selected from the group consisting of amino, hydroxyl, sulfhydryl, carboxyl and carbonyl;
- reactive groups selected from the group consisting of succinimidyl ester, isothiocyanate, isocyanate, iodoacetamide, maleimide, sulfonyl halide, phosphoramidite, alkylimidate, arylimidate, acid halide, substituted hydrazines, substituted hydroxylamines, carbodiimides;
- and
- electron donating and withdrawing groups that shift the absorption and emission wavelengths of the fluorescent molecule.
Dependencies are inferred from the claim text.