Solventless synthesis of a Schiff base that forms highly fluorescent organic nanoparticles exhibiting aggregation-induced emission in aqueous media

ABSTRACT

A highly fluorescent solid state Schiff base compound (DBD) was synthesised using a green, solventless and fast approach in 30 sec. DBD shows almost no emission in THF solution, while it emits strong fluorescence in both dispersed nano-aggregates in the solution and as a powder, through a phenomenon known as aggregation-induced emission. Organic nanoparticles of DBD were prepared in aqueous solution using the nanoreprecipitation method with and without stabilizers. The nanoparticles exhibited strong, blue emission when the non-ionic surfactant, like triton X-100, was used as a stabilizer, and strong green emission when no surfactant or the cationic surfactant, like CTAB as a stabilizer was used. Using atomic force microscopy and dynamic light scattering, the sizes of the nanoparticles were found to be around 75 nm when prepared without surfactant, 50 nm when prepared using triton X-100, and 30 40 nm when prepared using CTAB. DBD nanoparticles show an emission maximum at 527 nm (pure green) in the cases of CTAB and no surfactant, while 400 nm emission is observed when triton X-100 is used. Finally, for practical applications, the new type of highly fluorescent organic nanoparticles (DBD) were chosen for on/off fluorescence switching nano sensor for detecting organic vapour.

KEYWORDS:

• fluorescent organic nanoparticle
• solventless synthesis
• aggregation-induced emission
• Schiff base

Acknowledgments

The authors would like to thank Genome Center at Koye University for their help with the fluorescence measurements. Thanks to Mr Omed Al-Jaff for helping with AFM measurements.

Disclosure statement

No potential conflict of interest was reported by the authors.