Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Kazuyuki Sato; Akira Kawasaki; Yukiko Karuo; Atsushi Tarui; Kentaro Kawai; Masaaki Omote

doi:10.3762/bjoc.16.117

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Beilstein J Org Chem. 2020 Jun 22:16:1411-1417. doi: 10.3762/bjoc.16.117. eCollection 2020.

Authors

Kazuyuki Sato¹, Akira Kawasaki¹, Yukiko Karuo¹, Atsushi Tarui¹, Kentaro Kawai¹, Masaaki Omote¹

Affiliation

¹ Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.

Abstract

Fluorescent molecules based on a fluorinated isoxazole scaffold were synthesized and investigated for their photochemical properties. The introduction of a fluorine substituent into 3,5-diarylisoxazoles led to an increase of fluorescence intensity and exhibited a redshift in the emission intensity. α-Fluorinated boron ketoiminates (F-BKIs) were also synthesized via a ring-opening reaction of 4-fluoroisoxazoles and exhibited highly fluorescent luminescence and aggregation-induced emission (AIE), showing promise as a new fluorophore.

Keywords: 4-fluoroisoxazoles; aggregation-induced emission; boron ketoiminates; fluorescent probe; α-fluorinated boron ketoiminates.