Slow and Fast Singlet Energy Transfers in BODIPY-gallium(III)corrole Dyads Linked by Flexible Chains

Abstract

Red (no styryl), green (monostyryl), and blue (distyryl) BODIPY-gallium(III) (BODIPY = boron-dipyrromethene) corrole dyads have been prepared in high yields using click chemistry, and their photophysical properties are reported. An original and efficient control of the direction of the singlet energy transfers is reported, going either from BODIPY to the gallium-corrole units or from gallium-corroles to BODIPY, depending upon the nature of the substitution on BODIPY. In one case (green), both directions are possible. The mechanism for the energy transfers is interpreted by means of through-space Förster resonance energy transfer (FRET).

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

“…11 Therefore, they should be an excellent energy acceptor from BODIPY. BODIPY can function as a either energy donor or acceptor, as has been demonstrated by the synthesis of a plethora of ET arrays, including BODIPY-porphyrin, 15 BODIPY-corrole, 16 and BODIPY-phthalocyanine 17 arrays. To the best of our knowledge, the only reported BODIPY-bacteriochlorin arrays includes non-covalent assemblies in lipid vesicles 18 or micelles, 19 where energy transfer from BODIPY to bacteriochlorins occurs.…”

Synthesis and regioselective functionalization of perhalogenated BODIPYs

“…In addition, the 3,5- and 2,3,5,6-thienyl functionalized BODIPYs typically show larger Stokes shifts than the phenyl analogues, due to increased geometry relaxation. 22 However, the thienyl groups also greatly decreased the quantum yields of the functionalized BODIPYs (< 0.1) due to their greater freedom of rotation compared with phenyl, which increases the amount of energy lost to non-radiative decay to the ground state.…”

3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

“…On the other hand, to the best of our knowledge, in the corrole field there is only one recent report on the exploitation of the Huisgen reaction, for the elaboration of the meso -phenyl substituent in order to prepare a BODIPY-corrole dyad 22 .…”