A pyrenyl-appended C-symmetric hexahomotrioxacalix[3]arene for selective fluorescence sensing of iodide

Abstract

A new C 3v -symmetric homooxacalix[3]arene L bearing pyrene moieties as fluorophore has been designed and synthesized. L exhibits a significant fluorescence quenching responses to I − even in the concurrent presence of other potentially competing anions. There is a good linear relationship between the fluorescence intensity and the concentration of I − ranging from 0 to 100 μM and the detection limit was calculated to be as low as 164 nM. The ligand L can be served as fluorescent chemosensor for highly selective, sensitive, and rapid detection of I − .

Advances in fluorescent and colorimetric sensors for anionic species

“…13c) in a unique fashion. Various groups have been engaged in the development of chemosensors based around macrocyclic receptor scaffolds which include polyamines, calixarenes, calixpyrroles and porphyrins [48][49][50][51][52][53][54][55][56]. Kataev and co-workers proposed the bicyclic, anthracene-containing receptor 21 as an OFF-ON chemosensor for nitrate in buffered aqueous solution [57].…”

Recent Advances in Luminescent Recognition and Chemosensing of Iodide in Water

“…Among those reported with NÀ H groups (Figure 6), the most efficient are calixarenes 14, [72] naphthalene-glycine-derivatives 15, [62] calix [4]pyrrole 16, [64] bisquinolinium salts 17-19, [63] donor-aceptor thiourea derivative 20, [74] polyaza-macrocycle 21, [73] and benzimidazole-based tripodal receptors 22. [65] A calix [3]arene bearing pyrene moieties 14 for selective chemosensing of I À was reported by Yamato and coworkers.…”

“…[65] A calix [3]arene bearing pyrene moieties 14 for selective chemosensing of I À was reported by Yamato and coworkers. [72] The quenching response by iodide-complexation through NH … I À interactions, allows to quantify it with limit of 164 nM even in the presence of common interfering anions.…”

Optical Chemical Sensing of Iodide Ions: A Comprehensive Review for the Synthetic Strategies of Iodide Sensing Probes, Challenges, and Future Aspects

“…It is presumed that the suitably arranged functionalized amides attached to hexahomotrioxacalix [3]arene might be good receptors for the iodide anions. Therefore, Xie et al [107] (2020) synthesized a C 3v -symmetrical hexahomotrioxacalix [3]arene ( 27) by a condensation reaction of cone-triacid with an excessive amount of 1-aminopyrene in the presence of 1-hydroxybenzotriazole (HoBt) and dicyclohexylcarbodiimide (DCC) as coupling agents (Scheme 19). The fluorescence of this sensor is quenched with the addition of iodide ions giving the detection limit of 164 nM.…”