Functional π-Gelators and Their Applications

In 2008, we reported a new class of pillar-shaped macrocyclic hosts, known as “pillar[n]arenes”. Today, pillar[n]arenes are recognized as key players in supramolecular chemistry because of their facile synthesis, unique pillar shape, versatile functionality, interesting host–guest properties, and original supramolecular assembly characteristics, which have resulted in numerous electrochemical and biomedical material applications. In this Review, we have provided historical background to macrocyclic chemistry, followed by a detailed discussion of the fundamental properties of pillar[n]arenes, including their synthesis, structure, and host–guest properties. Furthermore, we have discussed the applications of pillar[n]arenes to materials science, as well as their applications in supramolecular chemistry, in terms of their fundamental properties. Finally, we have described the future perspectives of pillar[n]arene chemistry. We hope that this Review will provide a useful reference for researchers working in th...

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Applications of Supramolecular Anion Recognition

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Polyethylene glycol and solutions of polyethylene glycol as green reaction media

Detection Ying Zhou,†,‡ Jun Feng Zhang, and Juyoung Yoon*,† †Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Korea ‡Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. China

Fluorescence and colorimetric chemosensors for fluoride-ion detection.

A series of thiosemicarbazone derivatives of benzo-15-crown-5 were synthesized efficiently at room temperature using hydrogenchloride acid (HCl) as catalyst. Their anion recognition properties of a, b and c were studied, the result show they exhibit highly selective binding and sensing of F−, MeCO2 − and n-C3H7CO2 − in CH3CN (F− > n-C3H7CO2 − > MeCO2 − > > Cl−, Br− and I−). Especially receptor c shows different UV-Vis spectrum of F− from MeCO2 −and C3H7CO2 −, in addition to the color of the solution change from colorless to yellow upon the addition of F−, these two points make it suitable to be used as colorimetric anion sensor to identify fluoride anion from other halide anions and carboxylate anions by naked-eye. The connection between receptor and anion is by hydrogen bonding interactions, the binding ratio is 1:1, which have been confirmed by UV-vis inspection spectra in CH3CN and 1HMR in DMSO-d6.

Synthesis of Thiosemicarbazone Derivatives of Benzo-15-crown-5 and Their Anion Recognition Properties

A colorimetric and fluorescent fluoride probe bearing phenolic hydroxy and imine groups has been designed and synthesised. This receptor could visually and spectroscopically recognise F−  with high selectivity over other anions. After the addition of fluoride ions to the solution of ([1,1′-biphenyl]-4,4′-diylbis (azanylylidene)) bis (methanylylidene)) bis (naphthalen-2-ol) (TY), since the deprotonation reaction occurred between the sensor and fluoride, the fluorescence intensity of the solution changed significantly. Furthermore, the quenched fluorescence caused by fluoride ions could be recovered upon the addition of calcium ions to this complex solution. This resulted in an ‘OFF-ON-OFF’ type sensing. In particular, an IMP logic gate has been proposed using the output obtained from the fluorescence studies. The fluorescence, UV-vis titration and 1H NMR titration experiments indicated that the effects might occur via a combined process including hydrogen bond and deprotonation between the sensor and F− .

A reversible dual-channel chemosensor for fluoride anion

A novel nitrogen mustard functionalized tripodal AIE compound act as prodrug for fluorescent imaging and anticancer

We synthesized a new cyanide (CN−) chemosensor CX based on a nucleophilic addition reaction prompted by cyanide ion, which could be used for highly selective and sensitive fluorescence turn-on detection of cyanide in aqueous media. The CX showed selective fluorescence recognition for CN−, the miscellaneous competitive anions (F−, Cl−, Br−, I−, AcO−, H2PO4−, HSO4−, ClO4−, S2−, PO43−, CO32− and SCN−) did not lead to any significant interference. The detection limit of the sensor towards CN− is 1.15 × 10−7 mol•L−1. The sensor has been successfully applied to estimate the cyanide ion in seeds of cherries. Test strips based on CX were fabricated, which could be used as a convenient and efficient CN− test kit to detect CN− in aqueous solution for “in-the-field” measurement.

Tai-Bao Wei

Papers

Synthesis of Thiosemicarbazone Derivatives of Benzo-15-crown-5 and Their Anion Recognition Properties

A reversible dual-channel chemosensor for fluoride anion

A novel nitrogen mustard functionalized tripodal AIE compound act as prodrug for fluorescent imaging and anticancer

A Turn‐On Fluorescence Chemosensor for Cyanide in Aqueous Media Based on a Nucleophilic Addition Reaction

Rapid and Selective Detection of Cyanide Anion by Enhanced Fluorescent Emission and Colorimetric Color Changes at Micromole Levels in Aqueous Medium