Versatile optical response of pyridylalkyl naphthalenediimides in the interaction with metal ions

• Published in: Journal of molecular structure Vol. 1236; p. 130277
• Main Authors: Castro-Riquelme, Christian L., Ochoa-Terán, Adrián, Roldán-Villegas, Itzel Yareli, Trujillo-Navarrete, Balter, Miranda-Soto, Valentín, Pérez-Sicairos, Sergio, Pina-Luis, Georgina, Reynoso-Soto, Edgar A., Labastida-Galván, Victoria, Ordoñez, Mario
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.07.2021
• Subjects: Cation removal; Dual response; Metal ion detection; Naphthalendiimides; Metal ion detection; Cation removal; Naphthalendiimides; Dual response
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.130277

•Pyridylalkyl mono-core substituted naphthalenedimides interact with metal ions.•The interaction of NDIs with of Cu2+ and Fe3+ induces a colorimetric change.•NDI-Cu2+ complexes act as Fe2+ and Mg2+ON/OFF fluorescent dual probes.•A selective interaction and removal of Hg2+ from water by these NDIs. In this work, the interaction of three different pyridylalkyl mono-core substituted naphthalenedimides (NDIs) with metal ions was studied by UV-Vis and fluorescence spectroscopy. The influence of pyridine substituents position, the spacer length, and solvent over the metal ion recognition was investigated. The most sensible responses observed were with Cu2+ and Fe3+ ions, showing a remarkable change in their colorimetric and fluorescent properties. The prior formation of NDI-Cu2+ (2a and 2b) complexes generates a unique response towards Fe2+ and Mg2+, promoting an OFF/ON response and a colorimetric change, acting as a dual probe for Cu2+ and Fe2+ or Cu2+ and Mg2+. Finally, NDIs 2b and 2c show a specific and selective response towards Hg2+ions in water, forming a solid complex removing the Hg2+ from the aqueous media achieving a removal efficiency up to 92%. NDIs 2b and 2c have potential as probes and removal of Hg2+ ions.