Structure and linkage assessment of T-shaped Pyrrolidine[60]Fullerene- and Isoxazoline[60]Fullerene-BODIPY-triarylamine hybrids

Eight novel C60-BODIPY-Triarylamine electroactive triads have been synthesized and characterized. Using pyrrolidine (PIR and BDPF series) and isoxazoline (ISO series) as linkers between the fullerene and the BODIPY-Triarylamine (-TAA) system, the effect of these linkers along with different functionalization on the TAA on the electronic properties were studied. Moreover, their photophysical and electrochemical properties were investigated by comparing them to the reference substances BDP, 10a, 10b, and C60. All C60-BODIPY-TAA derivatives absorb visible light strongly in a range between 535 and 563 nm, and photoexcitation of the BODIPY unit causes photo-induced electron transfer, producing the corresponding charge-separated species, which was confirmed by solvatochromic effects on fluorescence measurements. The direction of charge transfer was also revealed by their redox potentials. A better electron affinity was observed for the ISO series when compared with PIR and BDPF. Thermogravimetric analysis showed that the pyrrolidine derivatives are more stable than their isoxazoline analogs and the insertion of alkoxy units in the triads triggers a better thermal endurance in the studied compounds. [Display omitted] •Synthesized BODIPY triads were structurally, optically, and electrochemically characterized.•The solvatochromism properties of isoxazoline and pyrrolidine[60]Fullerene-BODIPY-triarylamine compounds were examined.•Photo-induced electron transfer between BODIPY, triarylamines and C60 moieties.•Alkoxy units in the triads improve thermal endurance in thermogravimetric analysis.