Multi-state amine sensing by electron transfers in a BODIPY probe

Area of Science:

• Chemical sensing
• Fluorescent probes
• Organic chemistry

Background:

• Amines are vital in industry and biology, necessitating sensitive detection methods.
• Existing turn-on amine sensors lack mechanisms based on single electron transfer (SET).
• Photoinduced electron transfer (PET) is a common fluorescence quenching mechanism.

Purpose of the Study:

• To develop a novel turn-on amine sensor utilizing SET.
• To investigate a new probe based on a BODIPY fluorophore and a quinolinium ring.
• To explore multi-mechanistic fluorescence modulation for amine detection.

Main Methods:

• Design and synthesis of a BODIPY-based fluorescent probe.
• Investigation of fluorescence response to varying aliphatic amine concentrations.
• Characterization of probe selectivity against aromatic amines, thiols, and alcohols.
• Analysis of fluorescence quenching mechanisms including PET and SET.

Main Results:

• The probe exhibits turn-on fluorescence at low aliphatic amine concentrations (0-10 mM) via SET.
• High amine concentrations (50 mM - 1 M) induce collisional quenching.
• The sensor demonstrates selectivity for aliphatic amines over aromatic amines, thiols, and alcohols.
• A multi-mechanistic fluorescence modulation was observed.

Conclusions:

• The developed probe is the first to use SET for turn-on amine sensing.
• The sensor exhibits multi-state and dose-responsive behavior.
• This work provides a new platform for developing advanced amine-sensitive probes.