Colorimetric detection of achiral anions and chiral carboxylates by a chiral thiourea-phthalimide dyad.
The chiral chemosensor 1, based on a thiourea-activated phthalimide, is available by four reaction steps from 4-nitrophthalimide. 1 detects fluoride, chloride, acetate, and dihydrogen phosphate anions by changes in UV-vis absorption. Fluoride in excess induces deprotonation whereas the other anions show only complex formation in the ground state. (1)H-NMR studies confirm the formation of these H-bonded complexes and the fluoride-induced receptor deprotonation in the recognition process. Moderate chiral recognition was observed for sodium D/L-lactate with K(ass)(D)/K(ass)(L) = 1.93.
Griesbeck
Axel G
AG
Department of Chemistry, University of Cologne, Greinstr. 4, 50939, Köln, Germany. griesbeck@uni-koeln.de
Hanft
Sebastian
S
Díaz Miara
Yrene
Y
D000838:Anions / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003124:Colorimetry / Q000379:methods*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009574:Nitro Compounds / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis / Q000737:chemistry*; D019354:Sodium Lactate / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
C555026:1-(2-benzyl-1,3-dioxoisoindolin-5-yl)-3-(1-phenylethyl)thiourea; D000838:Anions; D002264:Carboxylic Acids; D009574:Nitro Compounds; D010797:Phthalimides; C082211:4-nitrophthalimide; D013890:Thiourea; D019354:Sodium Lactate