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

Rocha-Ortiz JS, Montalvo-Acosta JJ, He Y, Insuasty A, Hirsch A, Brabec C, Ortiz A (2023)

Publication Type: Journal article

Publication year: 2023

Journal

Book Volume: 217

Article Number: 111445

DOI: 10.1016/j.dyepig.2023.111445

Abstract

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.

Authors with CRIS profile

Involved external institutions

Institut de Chimie de Strasbourg France (FR) University of Valle / Universidad del Valle (Univalle) Colombia (CO) Institución Universitaria Centro de Estudios Superiores María Goretti (IU CESMAG) Colombia (CO)

How to cite

APA:

Rocha-Ortiz, J.S., Montalvo-Acosta, J.J., He, Y., Insuasty, A., Hirsch, A., Brabec, C., & Ortiz, A. (2023). Structure and linkage assessment of T-shaped Pyrrolidine[60]Fullerene- and Isoxazoline[60]Fullerene-BODIPY-triarylamine hybrids. Dyes and Pigments, 217. https://doi.org/10.1016/j.dyepig.2023.111445

MLA:

Rocha-Ortiz, Juan S., et al. "Structure and linkage assessment of T-shaped Pyrrolidine[60]Fullerene- and Isoxazoline[60]Fullerene-BODIPY-triarylamine hybrids." Dyes and Pigments 217 (2023).

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