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US 8,476,461 B2Granted
Dipyrromethene-boron hydrophilic fluorescent compounds
AssigneeCentre National de la Recherche Scientifique (CNRS)
InventorsGilles Ulrich, Raymond Ziessel, Song-Lin Niu, Alexandre Haefele, Thomas Bura
Life of this patent
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Abstract
Dipyrromethene-boron hydrophilic fluorescent compounds The invention concerns fluorescent and hydrophilic compounds meeting following formula (I): wherein: S1 is a group of formula —C≡C-L′-A where L′ is a linkage group and A is a polar functional group; S2 is a —C≡C-L′-A group the same or different from S1; —F; —H; or a hydrocarbon chain optionally interrupted by one or more oxygen atoms, and use thereof, in particular in aqueous or hydrophilic media.
Claims16
A compound of formula (I):
- wherein:
- S1 is a group of formula —C≡C-L′-A in which:
- L′ is a linkage group which is
- a single bond, or
- a divalent hydrocarbon group chosen from the group consisting of straight or branched alkylenes optionally comprising one or more oxygen, nitrogen or sulphur atoms in their chain;
- straight or branched alkenylenes;
- straight or branched alkynylenes, and arylenes;
- or a divalent hydrocarbon chain composed of a chain of at least two divalent hydrocarbon groups of the aforementioned type;
- A is a polar functional group chosen from among sulphonate, sulphate, phosphate, ammonium, carboxylate, phosphonate, alkylammonium sulphate and polyoxyethylene groups;
- S2 is:
- a —C≡C-L′-A group identical to or different from S1, in which L′ and A have the aforementioned meanings;
- —F;
- —H;
- or
- a hydrocarbon chain, straight or branched, saturated or unsaturated, optionally interrupted by one or more oxygen, nitrogen or sulphur atoms, optionally cyclized in whole or in part, optionally aromatic and optionally functionalized, and
- each of groups R1, R2, R3, R4, R5, R6 or R7 each independently designates a —H group or a hydrocarbon chain, wherein the hydrocarbon chain is straight or branched, saturated or unsaturated, optionally interrupted by one or more oxygen atoms, optionally cyclized in whole or in part, optionally aromatic and/or optionally functionalized,
- provided that all or part of R1, R2, R3, R4, R5, R6 or R7 can be linked together to form a bridged form.
14 more elements
A method of conducting fluorescence analysis in an aqueous medium comprising:
- (a) providing in an aqueous media a fluorescent and hydrophilic compound meeting following formula (I):
- wherein:
- S1 is a group of formula —C≡C-L′-A in which:
- L′ is a linkage group which is
- a single bond;
- or
- a divalent hydrocarbon group chosen from the group consisting of straight or branched alkylenes optionally comprising one or more oxygen, nitrogen or sulphur atoms in their chain;
- straight or branched alkenylenes;
- straight or branched alkynylenes, and arylenes;
- or a divalent hydrocarbon chain consisting of a chain of at least two divalent hydrocarbon groups of the aforementioned type;
- A is a polar functional group chosen from among the sulphonate, sulphate, phosphate, ammonium, carboxylate, hydroxyl, phosphonate, alkylammonium sulphate and polyoxyethylene groups;
- S2 is:
- a —C≡C-L′-A group the same or different from S1, in which L′ and A have the aforementioned meanings;
- —F;
- —H;
- or
- a hydrocarbon chain, straight or branched, saturated or unsaturated, optionally interrupted by one or more oxygen, nitrogen or sulphur atoms, optionally cyclized in whole or in part, optionally aromatic and optionally functionalized;
- and
- each of the groups R1, R2, R3, R4, R5, R6 or R7 each independently designates an —H group or a straight or branched, saturated or unsaturated hydrocarbon chain, optionally interrupted by one or more oxygen atoms, optionally cyclized in whole or in part, optionally aromatic and optionally functionalized,
- on the understanding that all or part of R1, R2, R3, R4, R5, R6 or R7 can be linked together to form a bridged form;
- and
- (b) conducting said fluorescence analysis in said aqueous medium.
19 more elements
Dependencies are inferred from the claim text.