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 pyr-rolidine (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 de-rivatives 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.

Automated summary

Eight novel C60-BODIPY-Triarylamine electroactive triads were synthesized and characterized, and the effect of different linkers and functionalization on the electronic properties were studied. The compounds showed strong absorption of visible light and photo-induced electron transfer, confirmed by solvatochromic effects and redox potentials. The study also found that the pyrrolidine derivatives were more stable than isoxazoline analogs and alkoxy units improved thermal endurance.