Recent Advancements in Calix[4]pyrrole‐Based Anion‐Receptor Chemistry. Issue 18 (19th March 2015)

• Record Type: Journal Article
• Authors: Saha, Indrajit; Lee, Jeong Tae; Lee, Chang‐Hee
• Is Part Of: European journal of organic chemistry. Issue 18(2015)
• Page Start: 3859
• Page End: 3885
• Publication Date: 2015-03-19
• Subjects: Supramolecular chemistry -- Calixarenes -- Anions -- Recognition -- Hydrogen bonds -- Pi interactions -- Cytotoxicity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403701
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Calix[4]pyrroles and their congeners are conformationally flexible, nonplanar tetrapyrrolic macrocycles that can recognize anionic substrates. Although the mother calix[4]pyrrole was reported more than 100 years ago, anion recognition accompanied with conformational changes was first discovered in 1996. These compounds have shown preferential binding of halide anions such as fluoride and chloride as well as that of phosphate and carboxylate anions. Extensive efforts have been made to improve the affinity and selectivity. Continuous expansion of related research makes this easy‐to‐make macrocycle more promising. In this review, recent synthetic developments and the anion binding properties of newly developed calix[4]pyrroles are discussed and accomplishments to date are summarized. We hope that this review provides a seed for future developments in this area of chemistry. Abstract : Synthetic developments and anion‐binding properties of newly developed calix[4]pyrroles are extensively discussed and accomplishments to date are summarized. Specifically, the formation of supramolecular organic frameworks and the possibility of customizing nanoscale structures through noncovalent interactions such as hydrogen bonding, anion–π interactions, and Coulombic interaction are addressed.