Multimodal Metal Cation Sensing with Bis(macrocyclic) Dye

Abstract

The synthesis, electrochemical, optical, and cation sensing properties of a bis(macrocyclic) dye 1, in which the benzo-15-crown-5 and phenylazathia-15-crown-5 subunits are linked through a styryl pyridinium moiety, are reported. In this new ditopic receptor, the benzo-15-crown-5 macrocycle acts as a highly selective binding site for alkaline earth metal cations (Mg(II) and Ba(II)), whereas the phenylazathia-15-crown-5 displays a strong binding affinity towards soft heavy-metal cations (Hg(II) and Ag(I)). The pronounced changes of the absorption and fluorescence spectra of this bichromophoric dye observed upon different metal cation addition make the dye suitable for dual-wavelength analysis and offer an enticing potential for multitasking sensors.

Addressing of multiple-metal ions on a single platform

“…This strategy has been well-adapted by Tulyakova et al [88] who synthesized a bis(macrocyclic) dye 69 containing benzo-15-crown-5 and phenylazathia-15-crown-5 subunits as the two binding entities, linked through a styryl pyridinium moiety. The dye showed strong and selective binding affinities toward two different groups of metals; alkaline earth (Mg 2+ , Ba 2+ ) and heavy metal ions (Hg 2+ , Ag + ).…”

Supramolecular tuning of energy transfer efficiency and direction in a bis(styryl) dye–crown ether conjugate

“…Based on this difference, the attachment of different crown ethers with diverse het eroatom substitution to the two chromophoric parts of 1 enables the independent regulation of the optical properties of each chromophore by complexation with appropriate cations. For the present study, we have selected Mg 2+ and Hg 2+ cations as they have the most effective interaction with the corresponding crown ethers [22,23]. The metal cations were used as perchlorate salts.…”

Proof of principle of a purine D–A–D′ ligand based ratiometric chemical sensor harnessing complexation induced intermolecular PET

“…The latter strategy has already found its application in the development of organic solar cells, [2][3][4][5] as well as third generation organic light emitting diodes (OLEDs). [6][7][8] Furthermore, the D-A-D 0 structure based intramolecular chemical sensors have been reported for multimodal detection of metal cations 9 or acids. 10 The electron donating parts such as anisole and dimethylaniline are considered to be general for push-pull systems 1 and may be selected based on their strength.…”