Perfluoroalkylated Calix[4]pyrroles: Fluoride Ion Extraction from an Aqueous Medium

Maji, Sinchan; Mandal, Debaprasad

doi:10.1002/asia.201700897

Cited by 5 publications

(2 citation statements)

References 47 publications

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“…However, a host design with flexible meso -alkyl linkers connected to additional hydrogen bond donors can be beneficial for binding larger polyatomic anions 22 since it retains a relatively open calix[4]pyrrole cavity where the podand arms could wrap around an included guest. Aliphatic linkers in meso -substituents have proven efficient for inducing a large conformational change for a fluorescent chemosensor, 22 providing perfluoroalkylated calix[4]pyrroles for fluoride extraction, 6 meso -tetrahexyl calix[4]pyrroles as chloride 23 and cesium 24 extractants, and acrylamide functionalized precursors for anion selective polymer membranes. 25 However, for efficient anion binding the meso -alkyl arms should be on the same side of the binding cavity ( cis ), 16,18,19 which leads in some cases to a challenging isomer separation.…”

Section: Introductionmentioning

confidence: 99%

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Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups

Pamula¹,

Bulatov²,

Martínez‐Crespo³

et al. 2023

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

“…Anion binding with synthetic receptors is a rapidly evolving field producing applications in anion sensing, [1][2][3][4][5] extraction, [6][7][8][9] and transport. 10 Calix [4]pyrroles are a well-known class of neutral supramolecular receptors, where converging pyrrole rings provide hydrogen bond donors for anion binding.…”

Section: Introductionmentioning

confidence: 99%

Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups

Pamula¹,

Bulatov²,

Martínez‐Crespo³

et al. 2023

Org. Biomol. Chem.

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Calix[5]phyrin for Fluoride Ion Sensing with Visible and Near Infrared Optical Responses

Higashino

Kumagai

Imahori

2018

Chemistry An Asian Journal

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Fluoride (F ) ion sensing is an important topic due to its roles in health, medical, and environmental sciences. In this regard, colorimetric sensors with a near infrared (NIR) optical response are useful in biological systems because they can avoid interference from endogenous chromophores. Although calix[n]phyrins are highly attractive as sensors with the NIR optical response, studies on calix[n]phyrins are still limited owing to their intrinsic instability against ambient light and air. In this study, we report the synthesis and characterization of a new calix[5]phyrin bearing one sp -hybridized carbon atom as a π-expanded calix[n]phyrin. Upon addition of tetrabutylammonium fluoride, the calix[5]phyrin exhibited distinct NIR absorptions at 908 and 1064 nm as well as a visible color change. Importantly, it revealed an excellent selectivity for F ion. These results demonstrate that calix[5]phyrins are promising colorimetric and NIR sensors of F ion.

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Does Larger Cavity‐Size Really Help Bigger Anions to Bind? A Scrutiny on Core‐Expanded Calix[4]pyrroles and Their Properties

Giri,

Dash,

Guchhait

2023

ChemPlusChem

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Calix[4]pyrroles are an important class of oligopyrrolic macrocycles and have found applications in many diverse fields including anion recognition. To modulate the properties of the calix[4]pyrrole, several structural modifications are realized. The core‐expansion has attracted extra attention as it provides larger cavity‐size compared to parent calix[4]pyrrole(s). This review highlights the synthetic development of various core‐expanded calix[4]pyrroles and their applications in anion‐binding properties. Emphasis is given to the changes in the binding properties observed with expanded versions of calix[4]pyrrole(s) in both solution and the solid states. The expanded versions of calix[4]pyrrole do not always show higher binding affinities for larger anions as anticipated. Rather, they display reduced affinities with the anions. The truncated form or asymmetric nature of the expanded versions of calix[4]pyrrole does not probably allow to access all the available binding sites for the anions and hence reduced binding affinities are observed. The receptors which contain a greater number of binding sites and are somehow rigid or preorganized apparently show enhanced binding affinities for anions. The relative binding constants for halide series indicate that the enlarged molecules are more beneficial for largest iodide among others. However, most of the receptors show selectivity towards smallest fluoride over other anions studied.

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Perfluoroalkylated Calix[4]pyrroles: Fluoride Ion Extraction from an Aqueous Medium

Cited by 5 publications

References 47 publications

Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups

Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups

Calix[5]phyrin for Fluoride Ion Sensing with Visible and Near Infrared Optical Responses

Does Larger Cavity‐Size Really Help Bigger Anions to Bind? A Scrutiny on Core‐Expanded Calix[4]pyrroles and Their Properties

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