Selective sensing of anions with calix[4]pyrroles strapped with chromogenic dipyrrolylquinoxalines.
New calix[4]pyrroles bearing dipyrrolylquinoxaline as strapping elements have been synthesized and characterized by spectroscopic means. The binding behavior of these receptors at 25 degrees C was investigated first by proton NMR spectroscopy in CD(3)CN/DMSO-d(6) (9:1 v/v), as well as by UV-vis spectroscopy and isothermal titration calorimetry (ITC) in CH(3)CN/DMSO (97:3 v/v). The receptors displayed a selective colorimetric response when exposed to the fluoride, dihydrogen phosphate, and acetate anions (studied in the form of the corresponding tetrabutylammonium salts) and an enhanced affinity as compared to a comparable calix[4]pyrrole system lacking the dipyrrolylquinoxaline-containing strap.
Yoo
Jaeduk
J
Department of Chemistry and Institute of Basic Science, Kangwon National University, Chun-Chon 200-701 Korea.
Kim
Min-Soo
MS
Hong
Seong-Jin
SJ
Sessler
Jonathan L
JL
Lee
Chang-Hee
CH
D000838:Anions / Q000032:analysis*; D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D002151:Calorimetry / Q000379:methods; D003124:Colorimetry / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D000838:Anions; D011166:Porphyrins; D011810:Quinoxalines; C469811:calix(4)pyrrole; D047250:Calixarenes