Optically active crown ether‐based fluorescent sensor molecules: A mini‐review

Abstract

This mini‐review focuses on fluorescent optically active crown ethers (polymeric derivatives are not included) reported in the literature (according to our knowledge), of which enantiomeric recognition ability, and in some cases, also inorganic cation complexation properties, were investigated by the sensitive and versatile fluorescence spectroscopy. These crown ether‐based chemosensors contain various fluorophore signaling units such as binaphthyl, anthracene, pyrene, tryptophan, benzimidazole, terpyridine, acridine, phenazine, acridone, BODIPY, and another conjugated aromatic one.

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

“…5). It can be mentioned that other reported fluorescent optically active crown ethers, which were tested with these two types of guests, did not show such extent of difference in their binding affinities [21][22][23][24][25][26].…”

“…The first use of photophysical techniques for elucidation of chiral recognition by crown ethers was reported in 1980 [20]. Since then, other optically active crown ethers containing different fluorophore units have been synthesized to this purpose, and their enantiomeric discrimination abilities toward the enantiomers of primary amines, amino acids, amino alcohols, and their derivatives were investigated [21,22]. Some of them were tested with both protonated primary amines and amino acid esters [21][22][23][24][25][26].…”

Exploring N-BODIPYs as Privileged Scaffolds to Build Off/On Fluorescent Sensors by PET

“…As a proof of concept, we designed molecule 3, shown in Figure 3. This N-BODIPY fulfills the following features considered in the initial hypothesis for the development of off/on sensors: (1) BODIPY chromophore; (2) o-phenylene diamino moiety attached to the boron, which should cancel the fluorescence of the BODIPY by PET; (3) a crown ether attached to the phenylene ring for cation recognition (e.g., sodium cations) [15]; (4) possibility of inactivating the PET when the crown ether binds cations, owing to the diminished electron donor capability of the crown ether-substituted phenylene ring; and (5) synthetic accessibility through the methodology developed by us for N-BODIPYs, leading to low-cost sensors [14]. As we established earlier [14], N-BODIPYs can be prepared from F-BODIPYs and sulfonamides by nucleophilic substitution of fluorine.…”

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

“…[ 55 ] The studies mentioned above indicate that apart from cyclodextrin, other chiral compounds with distinctive architectures can serve as new platforms for developing chiral material systems intended for chiral detection, for instance, calixarenes [ 224,225 ] and crown ethers. [ 226,227 ] Calixarenes and crown ethers with chiral moieties can form inclusion complex with guests having commensurate size. Endowment them with chirality will lead to new types of chiral structures.…”