Cyanine dyes and synthesis methods thereof

A process for coupling a dye compound comprising the formula:

• wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from a group consisting of hydrogen, C1-C6 alkyl group, a C0-C4 alkyl group having a hydrophilic substituent selected from a group consisting of sulfonate, carboxylate, hydroxyl, substituted amines and quaternary amines, such that at least one of R1-R10, R9′ and R10′ is the C0-C4 alkyl group having the hydrophilic substituent;
• wherein Y1 and Y2 are each independently selected from a group consisting of:
• wherein Ra9, R′9, R10, and R′10 are each independently selected from a group consisting of C1-C6 alkyl, and a heteroatom substituted C1-C6 alkyl wherein the heteroatom is O, N or S;
• wherein R11 and R12 are each independently selected from a group consisting of R14H, R14SH, R14NH2 and R14OH;
• wherein R14 is selected from a group consisting of:
• C3-C30 alkyl and C3-C30 alkyl having a phenyl, hydroxyl, sulfonyl, or halogen atom or a heteroatom substituted phenyl;
• and
• L is selected from a group consisting of:
• methine, a methine group having a substituent C1-C30 alkyl group and a methine group having a substituted C1-C30 alkyl group having a phenyl, hydroxyl, sulfonyl, a halogen atom, a heteroatom substituted phenyl or a C1-C4 alkoxyl where n is 1, 2, 3 or greater to a target molecule which comprises:
• reacting said compound (2) wherein at least one of R11 or R12 is selected from a group consisting of R14SH, R14NA2 and R14OH with said target molecule containing a moiety susceptible to nucleophilic addition of R14SH or R14NH or R14OH.

A process for coupling a dye compound comprising the formula:

• wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from a group consisting of hydrogen, C1-C6 alkyl group, a C0-C4 alkyl group having a hydrophilic substituent selected from a group consisting of sulfonate, carboxylate, hydroxyl, substituted amines and quaternary amines, such that at least one of R1-R10, R9′ and R10′ is the C0-C4 alkyl group having the hydrophilic substituent;
• wherein Y1 and Y2 are each independently selected from a group consisting of:
• wherein R9, R′9, R10, and R′10 are each independently selected from a group consisting of C1-C6 alkyl, and a heteroatom substituted C1-C6 alkyl wherein the heteroatom is O, N or S;
• wherein R11 and R12 are each independently selected from a group consisting of R14H, R14SH, and R14OH;
• wherein R14 is selected from a group consisting of:
• C3-C30 alkyl and C3-C30 alkyl having a phenyl, hydroxyl, sulfonyl, or halogen atom or a heteroatom substituted phenyl;
• and
• L is selected from a group consisting of:
• methine, a methine group having a substituent C1-C30 alkyl group and a methane group having substituted C1-C30 alkyl group having a phenyl, hydroxyl, sulfonyl, a halogen atom, a heteroatom substituted phenyl or a C1-C4 alkoxyl where n is 1, 2, 3 or greater to a target molecule which comprises:
• reacting said compound (2) wherein at least one of R11 or R12 is selected from a group consisting of:
• R14SH and R14OH with said target molecule containing a moiety susceptible to nucleophilic addition of R14SH or R14OH.

A process for coupling a dye compound comprising the formula:

• wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from a group consisting of hydrogen, C1-C6 alkyl group, a C0-C4 alkyl group having a hydrophilic substituent selected from a group consisting of sulfonate, carboxylate, hydroxyl, substituted amines and quaternary amines, such that at least one of R1-R10, R9 and R10 is the C0-C4 alkyl group having the hydrophilic substituent;
• wherein Y1 and Y2 are each independently selected from a group consisting of:
• wherein Ra9, R′9, R10, and R′10 are each independently selected from a group consisting of C1-C6 alkyl, and a heteroatom substituted C1-C6 alkyl wherein the heteroatom is O, N or S;
• wherein R11 and R12 are each independently selected from a group consisting of R14H, R14NH2 and R14OH;
• wherein R14 is selected from a group consisting of:
• C3-C30 alkyl and C3-C30 alkyl having a phenyl, hydroxyl, sulfonyl, or halogen atom or a heteroatom substituted phenyl when R11 or R12 are each independently selected from a group consisting of R14H and R14OH, wherein R14 is selected from a group consisting of:
• C6-C30 alkyl and C6-C30 alkyl having a phenyl, hydroxyl, sulfonyl, or halogen atom or a heteroatom substituted phenyl when R11 and R12 are each independently R14NH2;
• and
• L is selected from a group consisting of:
• methine, a methine group having a substituent C1-C30 alkyl group and a substituted C1-C30 alkyl group having a phenyl, hydroxyl, sulfonyl, a halogen atom, a heteroatom substituted phenyl and a C1-C4 alkoxyl where n is 1, 2, 3 or greater to a target molecule which comprises:
• reacting said compound (2) wherein at least one of R11 or R12 is selected from a group consisting of R14NH2 and R14OH with said target molecule containing a moiety susceptible to nucleophilic addition of R14NH2 or R14OH.