Fluorescent polymers soluble in an aqueous solution and a method for the production thereof

A method for preparing fluorescent polymers soluble in an aqueous solution, which have a fluorescence amplification factor of greater than or equal to 0.35 per kg/mol of polymer, comprising the following steps:

• a step of random copolymerization carried out with a functionalized monomer carrying a reactive function X1, optionally in protected form, so as to obtain a polymer carrying at least 5 reactive functions X1, optionally in protected form, distributed on said polymer,
• a step of coupling at least 5 fluorophores onto at least a part of the reactive functions X1, after optionally deprotection of said reactive functions, said fluorophores exhibiting the following characteristics:
• the fluorophores are water-soluble,
• the fluorophores are not self-associated in water at a concentration of less than or equal to 10−4 mol/l,
• the fluorophores which are free in the aqueous solution have a molar extinction coefficient of greater than 1000 M−1 cm−1 and
• the fluorophores which are free in the aqueous solution have a quantum yield of greater than 0.3, wherein:
• the fluorophores are selected from the group consisting of N-(5-aminopentyl)-4-amino-3,6-disulfo-1,8-naphthalimide, 3,6-diamino-9-(2-methoxycarbonyl)phenyl, 9-(2,4-disulfophenyl)-2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-xantheno[2,3,4-ij:5,6,7-i′j′]diquinolizin-18-ium, 9-(2,4-disulfophenyl)-3,6-bis(ethylamino)-2,7-dimethylxanthylium, 3,6-bis(diethylamino)-9-(2,4-disulfophenyl)′xanthylium, and derivatives thereof;
• and
• wherein said polymer:
• is in the form of a random copolymer, comprising at least two distinct repeat entities, one entity carrying the fluorophore and at least one other hydrophilic entity,
• has a polydispersity index of less than 1.5,
• is obtained using a living ionic polymerization or controlled radical polymerization method, and
• has less than 2.4 kg/mol of polymer per fluorophore.

A method for preparing fluorescent polymers soluble in an aqueous solution, which have a fluorescence amplification factor of greater than or equal to 0.35 per kg/mol of polymer, which method implements a step of polymerization by copolymerization of a functionalized monomer carrying a fluorophore, with a hydrophilic monomer, or else with a monomer which, after treatment, can produce a hydrophilic entity, said fluorophores exhibiting the following characteristics:

• the fluorophores are water-soluble,
• the fluorophores are not self-associated in water at a concentration of less than or equal to 10−4 mol/l,
• the fluorophores which are free in the aqueous solution have a molar extinction coefficient of greater than 1000 M−1 cm−1 and
• the fluorophores which are free in the aqueous solution have a quantum yield of greater than 0.3, wherein:
• the fluorophores are selected from the group consisting of N-(5-aminopentyl)-4-amino-3,6-disulfo-1,8-naphthalimide, 3,6-diamino-9-(2-methoxycarbonyl)phenyl, 9-(2,4-disulfophenyl)-2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-xantheno[2,3,4-ij:5,6,7i′j′]diquinolizin-18-ium, 9-(2,4-disulfophenyl)-3,6-bis(ethylamino)-2,7-dimethylxanthylium, 3,6-bis(diethylamino)-9-(2,4-disulfophenyl)′xanthylium, and derivatives thereof;
• and
• wherein said polymer:
• is in the form of a random copolymer, comprising at least two distinct repeat entities, one entity carrying the fluorophore and at least one other hydrophilic entity,
• has a polydispersity index of less than 1.5,
• is obtained using a living ionic polymerization or controlled radical polymerization method, and
• has less than 2.4 kg/mol of polymer per fluorophore.