Synthesis of a new tripod BODIPY dye bearing N-tert-Butoxycarbonyl amine and its acetylation

Abstract

A new tripod boron dipyrromethene (BODIPY) dye bearing N-tert-butoxycarbonyl (N-Boc) amine side chain was synthesized and the functionality was confirmed by means of its acetylation reaction with acetic anhydride. Deprotection of the N-Boc protective group had been successfully performed using boron trifluoride etherate (BF₃·OEt₂) solution alone or the combination of BF₃·OEt₂ and molecular sieves to solve the susceptibility of the BODIPY fluorophore under the protonic acid conditions. All the new structures had been characterized by NMR, HRMS and IR spectra. A conformational isomeric phenomenon was observed originating from partly restricted rotation of the RNH group attached to the 1,3,5-triazine ring. This work made the chemical transformation via amine functionality around meso position in the tripod BODIPY available.

Graphical Abstract

Keywords:

• Acetylation
• boron dipyrromethene (BODIPY)
• deprotection
• N-tert-butoxycarbonyl amine
• tripod

Additional information

Funding

We are thankful to the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for partial financial support.