Matches in SemOpenAlex for { <https://semopenalex.org/work/W2323088590> ?p ?o ?g. }
- W2323088590 endingPage "8456" @default.
- W2323088590 startingPage "8450" @default.
- W2323088590 abstract "Fluorescent pyrid-2-yl ureas were prepared by treating halogenated 2-aminopyridines with hexyl isocyanate, followed by Sonogashira coupling with arylacetylenes. The sensors emit light of ∼360 nm with quantum yields of 0.05−0.1 in acetonitrile solution. Addition of strong organic acids (pKa < 13 in CH3CN) shifts the fluorescence band to lower energy, and clean isoemissive behavior is observed. Fluorescence response curves (i.e., F/F0 vs [acid]total) are hyperbolic in shape for CCl3COOH and CF3COOH, with association constants on the order of 103 M−1 for both acids. 1H NMR titrations and DFT analyses indicate that trihaloacetic acids bind in ionized form to the receptors. Pyridine protonation disrupts an intramolecular H-bond, thereby unfolding an array of ureido NH donors for recognition of the corresponding carboxylates. Methanesulfonic acid protonates the sensors, but no evidence for conjugate base binding at the urea moiety is found by NMR. An isosteric control compound that lacks an integrated pyridine does not undergo significant fluorescence changes upon acidification." @default.
- W2323088590 created "2016-06-24" @default.
- W2323088590 creator A5000622722 @default.
- W2323088590 creator A5063027954 @default.
- W2323088590 creator A5063722899 @default.
- W2323088590 creator A5079118435 @default.
- W2323088590 date "2010-11-16" @default.
- W2323088590 modified "2023-09-28" @default.
- W2323088590 title "Binding of Carboxylic Acids by Fluorescent Pyridyl Ureas" @default.
- W2323088590 cites W1963626020 @default.
- W2323088590 cites W1965208008 @default.
- W2323088590 cites W1965752441 @default.
- W2323088590 cites W1966750682 @default.
- W2323088590 cites W1973884822 @default.
- W2323088590 cites W1974990674 @default.
- W2323088590 cites W1975193123 @default.
- W2323088590 cites W1981661275 @default.
- W2323088590 cites W1982761066 @default.
- W2323088590 cites W1985857283 @default.
- W2323088590 cites W1990856610 @default.
- W2323088590 cites W1992181652 @default.
- W2323088590 cites W1993361534 @default.
- W2323088590 cites W1996027805 @default.
- W2323088590 cites W2004751384 @default.
- W2323088590 cites W2005060486 @default.
- W2323088590 cites W2010539518 @default.
- W2323088590 cites W2010954800 @default.
- W2323088590 cites W2014551800 @default.
- W2323088590 cites W2018576132 @default.
- W2323088590 cites W2019983293 @default.
- W2323088590 cites W2023025198 @default.
- W2323088590 cites W2040590035 @default.
- W2323088590 cites W2043858812 @default.
- W2323088590 cites W2044271675 @default.
- W2323088590 cites W2051541893 @default.
- W2323088590 cites W2052229973 @default.
- W2323088590 cites W2053649382 @default.
- W2323088590 cites W2054595771 @default.
- W2323088590 cites W2058322651 @default.
- W2323088590 cites W2068789494 @default.
- W2323088590 cites W2070127123 @default.
- W2323088590 cites W2071491057 @default.
- W2323088590 cites W2071504445 @default.
- W2323088590 cites W2082986749 @default.
- W2323088590 cites W2085232511 @default.
- W2323088590 cites W2090791055 @default.
- W2323088590 cites W2146304364 @default.
- W2323088590 cites W2152324904 @default.
- W2323088590 cites W2164109095 @default.
- W2323088590 cites W2916225125 @default.
- W2323088590 doi "https://doi.org/10.1021/jo101730w" @default.
- W2323088590 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21080667" @default.
- W2323088590 hasPublicationYear "2010" @default.
- W2323088590 type Work @default.
- W2323088590 sameAs 2323088590 @default.
- W2323088590 citedByCount "18" @default.
- W2323088590 countsByYear W23230885902012 @default.
- W2323088590 countsByYear W23230885902013 @default.
- W2323088590 countsByYear W23230885902015 @default.
- W2323088590 countsByYear W23230885902016 @default.
- W2323088590 countsByYear W23230885902018 @default.
- W2323088590 countsByYear W23230885902019 @default.
- W2323088590 countsByYear W23230885902021 @default.
- W2323088590 crossrefType "journal-article" @default.
- W2323088590 hasAuthorship W2323088590A5000622722 @default.
- W2323088590 hasAuthorship W2323088590A5063027954 @default.
- W2323088590 hasAuthorship W2323088590A5063722899 @default.
- W2323088590 hasAuthorship W2323088590A5079118435 @default.
- W2323088590 hasConcept C103319777 @default.
- W2323088590 hasConcept C121332964 @default.
- W2323088590 hasConcept C145148216 @default.
- W2323088590 hasConcept C155647269 @default.
- W2323088590 hasConcept C161790260 @default.
- W2323088590 hasConcept C17814232 @default.
- W2323088590 hasConcept C178790620 @default.
- W2323088590 hasConcept C184866935 @default.
- W2323088590 hasConcept C185592680 @default.
- W2323088590 hasConcept C2776568683 @default.
- W2323088590 hasConcept C2777463227 @default.
- W2323088590 hasConcept C2779485729 @default.
- W2323088590 hasConcept C30095370 @default.
- W2323088590 hasConcept C502130503 @default.
- W2323088590 hasConcept C61442700 @default.
- W2323088590 hasConcept C62520636 @default.
- W2323088590 hasConcept C71240020 @default.
- W2323088590 hasConcept C75079739 @default.
- W2323088590 hasConcept C75473681 @default.
- W2323088590 hasConcept C91881484 @default.
- W2323088590 hasConceptScore W2323088590C103319777 @default.
- W2323088590 hasConceptScore W2323088590C121332964 @default.
- W2323088590 hasConceptScore W2323088590C145148216 @default.
- W2323088590 hasConceptScore W2323088590C155647269 @default.
- W2323088590 hasConceptScore W2323088590C161790260 @default.
- W2323088590 hasConceptScore W2323088590C17814232 @default.
- W2323088590 hasConceptScore W2323088590C178790620 @default.
- W2323088590 hasConceptScore W2323088590C184866935 @default.
- W2323088590 hasConceptScore W2323088590C185592680 @default.
- W2323088590 hasConceptScore W2323088590C2776568683 @default.