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US 12,644,871 B2Granted
Detection of nitrates and their decomposition products by means of fluorescence measurement
AssigneeBunderspublik Deutschland, vetreten durch den Bundesminister für Wirtschaft und Energie
InventorsBenedikt Heller, Mustafa Biyikal, Knut Rurack, Jerie Zbynek
Life of this patent
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Abstract
A molecular probe for selective detection of a nitrate and/or a decomposition product of a nitrate by generating a fluorescence signal in response to an excitation in the wavelength range between 340-370 and 480-520 nm, wherein the molecular probe is selected from a triarylborane dye according to formula (7) and a BODIPY™ (boron-dipyrromethene) dye according to formula (13):
Claims18
A molecular probe,
- wherein the molecular probe is configured for selective detection of a nitrate and/or a decomposition product of a nitrate by generating a fluorescence signal in response to an excitation at 365 nm,
- wherein the molecular probe is a triarylborane dye according to formula (7):
- wherein
- R1 is selected from the group consisting of NHCH2CH2NH2, NHCH2CH2NH(alkyl), NHCH2CH2NHPh, NHCH2CH2NHAr, NHNH2, NHNHMe, NHNHPh, NHNHAr, NHNHCH2CH2NH2, NHNHCH2CH2NH(alkyl), NHNHCH2CH2NHPh, NHNHCH2CH2NHAr, CO—NHCH2CH2NH2, CO—NHNH2, CO—NHNHMe, CO—NHNHCH2CH2NH2, CO—NHNHCH2CH2NHPh, CO—NHNHCH2CH2NHAr, NH—CO—NHNH2, NHNH—CO—NHNH2, NHNH—CO—NH2, NH—CS—NHNH—CO—Me, NH—CO—NHNH—CO—Me, CO—NHNH—CS—NH2, NH—CS—NHNH—CO-alkyl, CO—NHNH—CS—NH(alkyl),
- and regioisomers of the amine groups of (a)-(d);
- R17 is selected from the group consisting of H, Me, alkyl, phenyl, benzyl, aryl, F, Cl, Br, I, CF3, NH2, NO2, CO2H, CH2OH, CH2O(alkyl), CH2NMe2, CH2N(alkyl)2, OH, OMe, OiPr, and O(alkyl);
- R18 is selected from the group consisting of H, Me, alkyl, phenyl, benzyl, aryl, F, Cl, Br, I, CF3, NH2, NO2, CO2H, CH2OH, CH2O(alkyl), CH2NMe2, CH2N(alkyl)2, OH, OMe, OiPr, and O(alkyl);
- R19 is selected from the group consisting of H, Me, alkyl, phenyl, benzyl, aryl, F, Cl, Br, I, CF3, NH2, NO2, CO2H, CH2OH, CH2O(alkyl), CH2NMe2, CH2N(alkyl)2, OH, OMe, OiPr, and O(alkyl);
- R20 is selected from the group consisting of H, Me, Et, alkyl, phenyl, benzyl, aryl, CF3, CO—Me, CO-alkyl, CO-aryl, NH2, OMe, OiPr, and O(alkyl);
- R21 is selected from the group consisting of H, Me, Et, alkyl, phenyl, benzyl, aryl, CF3, CO—Me, CO-alkyl, CO-aryl, NH2, OMe, OiPr, and O(alkyl);
- R22 is H,
- each of R9, R10, R11, R12, R13, and R14 is independently selected from the group consisting of H, Me, alkyl, phenyl, benzyl, aryl, F, Cl, Br, I, —CF3, —CH2OH, —CH2Oalkyl, —CH2NMe2, —CH2N(alkyl)2, —CH2P(tBu)2, —CH2P(alkyl)2, —OMe, —OiPr, —O(alkyl), —NH2, —NHMe, —NH(alkyl), —NEt2, —N(alkyl)2, —NHPh, —NHAr, —NHNH2, —NHNHMe, —NHNMe2, —NHNEt2, —NHN(alkyl)2, —NHNHPh, —NHNHAr, —NHNPh2, —NHNAr2, —CO—NH2, —CO—NHMe, —CO—NMe2, —CO—NEt2, —CO—N(alkyl)2, —CO—NHPh, —CO—NHAr, —CO—NHNH2, —CO—NHNHMe, —CO—NHNMe2, —CO—NHNEt2, and —CO—NHN(alkyl)2,
- and
- i) each of R15, and R16 is independently selected from the group consisting of H, Me, alkyl, phenyl, benzyl, aryl, F, Cl, Br, I, —CF3, —CH2OH, —CH2O(alkyl), —CH2NMe2, —CH2N(alkyl)2, —CH2P(tBu)2, —CH2P(alkyl)2, —OMe, —OiPr, —O(alkyl), —NH2, —NHMe, —NH(alkyl), —NEt2, —N(alkyl)2, —NHPh, —NHAr, —NHNH2, —NHNHMe, —NHNMe2, —NHNEt2, —NHN(alkyl)2, —NHNHPh, —NHNHAr, —NHNPh2, —NHNAr2, —CO—NH2, —CO—NHMe, —CO—NMe2, —CO—NEt2, —CO—N(alkyl)2, —CO—NHPh, —CO—NHAr, —CO—NHNH2, —CO—NHNHMe, —CO—NHNMe2, —CO—NHNEt2, and —CO—NHN(alkyl)2,
- or
- ii) each of R15, and R16 is selected from the group consisting of H, F, Cl, Br, I, Me, alkyl, phenyl, aryl, vinyl, alkynyl, CF3, NMe2, NPh2, and BMes2;
- or
- iii) each of R15 and R16 is independently selected from the group consisting of
- with
- n and m being independently selected from the group consisting of 0, 1, 2, 3, and 4;
- wherein n+m≥1.
18 more elements
Dependencies are inferred from the claim text.