Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing

• Main Authors: Ádám Golcs, Korinna Kovács, Panna Vezse, Tünde Tóth, Péter Huszthy
• Format: Article
• Language: English
• Published: MDPI AG 2021-07-01
• Series: Molecules
• Subjects: acridine; macrocycles; metal ion complexation; fluorescence; optochemical sensor
• Online Access: https://www.mdpi.com/1420-3049/26/13/4043

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 log<i>K</i> > 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 <i>N</i>-substituents of the new host-backbone provides diverse opportunities in both immobilization and practical applications without influencing the molecular recognition abilities.