Abstract

Acridino-diaza-20-crown-6 ether derivatives as new turn-on type fluorescent chemosensors with an excellent functionality and photophysical properties have been designed and synthesized for metal ion-selective optochemical sensing applications. Spectroscopic studies revealed that in an acetonitrile-based semi-aqueous medium, the sensor molecules exhibited a remarkable fluorescence enhancement with high sensitivity only toward Zn2+, Al3+ and Bi3+, among 23 different metal ions. Studies on complexation showed a great coordinating ability of logK > 4.7 with a 1:1 complex stoichiometry in each case. The detection limits were found to be from 59 nM to micromoles. The new ionophores enabled an optical response without being affected either by the pH in the range of 5.5–7.5, or the presence of various anions or competing metal ions. Varying the N-substituents of the new host-backbone provides diverse opportunities in both immobilization and practical applications without influencing the molecular recognition abilities.

Highlights

  • Acridine and its derivatives have been extensively studied

  • Ingly, acridines have foryears manyalso years become widespread in of thesupramolecular field of supramolecacridines have for many become widespread in the field chemular chemistry

  • Reagent.Since, Since,in in our our experience, experience,the thecommercially commerciallyavailable availablereagent reagentdid didnot not have the proper quality, the alkylating agent was freshly prepared according to a previously have the proper quality, the alkylating agent was freshly prepared according to a previreported procedure outlined in Scheme ously reported procedure as outlined in Scheme

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Summary

Introduction

Acridine and its derivatives have been extensively studied. Researchers typically pay attention to tothe thefavorable favorablefluorescent fluorescent properties of these heterocyclic dyes.Unsurprisproperties of these heterocyclic dyes.Unsurprisingly, ingly, acridines have foryears manyalso years become widespread in of thesupramolecular field of supramolecacridines have for many become widespread in the field chemular chemistry.They usually play anrole important role as optochemically active units of senistry.They usually play an important as optochemically active units of sensor molecules sor providing molecules the by providing the signaling the sensing process.toInthe addition to by signaling function in thefunction sensinginprocess. Researchers typically pay attention to tothe thefavorable favorablefluorescent fluorescent properties of these heterocyclic dyes. Ingly, acridines have foryears manyalso years become widespread in of thesupramolecular field of supramolecacridines have for many become widespread in the field chemular chemistry. They usually play anrole important role as optochemically active units of senistry. They usually play an important as optochemically active units of sensor molecules sor providing molecules the by providing the signaling the sensing process.toInthe addition to by signaling function in thefunction sensinginprocess

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