Synthesis and properties of triazole bridged BODIPY-conjugates

A series of triazole bridged BODIPY-conjugates were synthesized under click reaction conditions. The 3-azido BODIPY was generated in situ by treating 3-bromo BODIPY with NaN3 in CH3CN at room temperature for 60 min and reacted with appropriate ethynyl containing chromophore/redox active unit, such as ferrocene, BODIPY, Zn(II) porphyrin, 21,23-dithiaporphyrin, BF2-smaragdyrin in the presence of CuI/DIPEA in THF/CH3CN solvent. The conjugates were purified by column chromatography and obtained pure compounds in 45-50% yields. The conjugates were characterized by HR-MS, 1D, 2D, F-19 and B-11 NMR and X-ray crystallography for BODIPY-ferrocene conjugate. Absorption and electrochemical studies showed features of both the moieties present in the conjugates and also support interaction between the two moieties in the conjugates. The fluorescence studies supported an efficient energy transfer from BODIPY unit to BF2-smaragdyrin unit in BODIPY BF2-smaragdyrin conjugate but the energy transfer was not efficient in BODIPY-Zn(II) porphyrin and BODIPY-21,23-dithiaporphyrin conjugates. (C) 2013 Elsevier Ltd. All rights reserved.