Synthesis of a novel tripod BODIPY dye bearing N-hydroxysuccinimide ester and its amidation

ABSTRACT

A novel tripod boron dipyrromethene (BODIPY) dye bearing N-hydroxysuccinimide ester was synthesized through its carboxylic acid precursor, and the functionality was confirmed by its amidation reaction with a primary amine. It is the first time that a reactive functional group was introduced onto a tripod BODIPY structure. All the new structures had been characterized by NMR, HRMS, and IR spectra. The introduction of an electron-donative diethylamine proved to be a key factor for the successful hydrogenolysis of the corresponding tris-substituted 1,3,5-triazine structure.

GRAPHICAL ABSTRACT

KEYWORDS:

• Amidation
• boron dipyrromethene (BODIPY)
• hydrogenolysis
• N-hydroxysuccinimide ester
• tripod

Additional information

Funding

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