A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications

Edison Castro; Maira R. Cerón; Andrea Hernandez Garcia; Quentin Kim; Alvaro Etcheverry-Berríos; Mauricio J. Morel; Raúl Díaz-Torres; Wenjie Qian; Zachary Martinez; Lois Mendez; Frank Perez; Christy A. Santoyo; Raquel Gimeno-Muñoz; Ronda Esper; Denisse A. Gutierrez; Armando Varela-Ramirez; Renato J. Aguilera; Manuel Llano; Monica Soler; Núria Aliaga-Alcalde; Luis Echegoyen

doi:10.1039/C8RA08334G

A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications†

Edison Castro,

*^a Maira R. Cerón,

^ab Andrea Hernandez Garcia,^a Quentin Kim,^a Alvaro Etcheverry-Berríos,

^c Mauricio J. Morel,

^c Raúl Díaz-Torres,^d Wenjie Qian,^d Zachary Martinez,^e Lois Mendez,^a Frank Perez,^a Christy A. Santoyo,^a Raquel Gimeno-Muñoz,^d Ronda Esper,^a Denisse A. Gutierrez,

^e Armando Varela-Ramirez,

^e Renato J. Aguilera,^e Manuel Llano,^e Monica Soler,

^c Núria Aliaga-Alcalde

^df and Luis Echegoyen

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, The University of Texas at El Paso, 500W University Ave, El Paso, TX 79968, United States
E-mail: eacastroportillo@utep.edu, echegoyen@utep.edu

^b Physical and Life Sciences, Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA

^c Departamento de Ingeniería Química, Biotecnología y Materiales, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Beauchef 851, Santiago, Chile

^d CSIC-ICMAB (Institut de Ciéncia dels Materials de Barcelona), Campus de la Universitat Autónoma de Barcelona, 08193 Bellaterra, Spain

^e Department of Biological Sciences, Border Biomedical Research Center, The University of Texas at El Paso, 500 West University Avenue, El Paso, TX 79968, USA

^f ICREA (Institució Catalana de Recerca i Estudis Avançats), Passeig Lluís Companys 23, 08010 Barcelona, Spain

Abstract

The synthesis and characterization of a family of [60]fullerocurcuminoids obtained via Bingel reactions is reported. The new C₆₀ derivatives include curcumin and curcuminoids with a variety of end groups. Preliminary biological experiments show the potential activity of the compound containing a curcumin addend, which exhibits moderate anti-HIV-1 and radical scavenger properties, but no anti-cancer activity. In addition, the new fullerocurcuminoids exhibit HOMO/LUMO energy levels that are reasonably matched with those of perovskites and when they were tested in perovskite solar cells (PSCs) as the electron transporting material (ETM), photoconversion efficiencies ranging from 14.04–14.95% were obtained, whereas a value of 16.23% was obtained for [6,6]-phenyl-C₆₁-butyric acid methyl ester (PC₆₁BM) based devices.

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A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications†

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