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

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.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [1];  [1]; ORCiD logo [3]; ORCiD logo [3];  [4];  [4];  [5];  [1];  [1];  [1];  [4];  [1]; ORCiD logo [5]; ORCiD logo [5];  [5];  [5]; ORCiD logo [3]; ORCiD logo [6] more »; ORCiD logo [1] « less
  1. Univ. of Texas at El Paso, TX (United States). Dept. of Chemistry
  2. Univ. of Texas at El Paso, TX (United States). Dept. of Chemistry; Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Physical and Life Sciences
  3. Univ. de Chile, Santiago (Chile). Facultad de Ciencias Fisicas Y Matematicas, Dept. de Ingenieria Quimica, Biotechnolgia y Materiales
  4. Univ. Autónoma de Barcelona, Bellaterra (Spain). Inst. de Ciencia de Materials de Barcelona (ICMAP-CSIC)
  5. Univ. of Texas at El Paso, TX (United States). Dept. of Biological Sciences, Border Biomedical Research Center
  6. Univ. Autónoma de Barcelona, Bellaterra (Spain). Inst. de Ciencia de Materials de Barcelona (ICMAP-CSIC); Inst. Catalana de Recerca i Estudis Avançats (ICREA), Barcelona (Spain)
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States); Univ. of Texas at El Paso, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC); National Science Foundation (NSF); Robert A. Welch Foundation; National Fund for Scientific and Technological Development (FONDECYT); Comisión Nacional de Investigación Científica y Tecnológica (Conicyt); Spanish Government; Centres of Excellence in R&D; Generalitat de Catalunya; Fundacio Montcelimar; Consejo Superior de Investigaciones Científicas (CSIC); National Institute of General Medical Sciences (NIGMS); National Institutes of Health (NIH); National Institute on Minority Health and Health Disparities (NIMHD)
OSTI Identifier:
1624960
Grant/Contract Number:  
AC52-07NA27344; AH-0033; 1161775, 3170509; 5 SC1 AI098238-02; 5G12MD007592
Resource Type:
Accepted Manuscript
Journal Name:
RSC Advances
Additional Journal Information:
Journal Volume: 8; Journal Issue: 73; Journal ID: ISSN 2046-2069
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry

Citation Formats

Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, and Echegoyen, Luis. A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications. United States: N. p., 2018. Web. doi:10.1039/c8ra08334g.
Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, & Echegoyen, Luis. A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications. United States. https://doi.org/10.1039/c8ra08334g
Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, and Echegoyen, Luis. Thu . "A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications". United States. https://doi.org/10.1039/c8ra08334g. https://www.osti.gov/servlets/purl/1624960.
@article{osti_1624960,
title = {A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications},
author = {Castro, Edison and Cerón, Maira R. and Garcia, Andrea Hernandez and Kim, Quentin and Etcheverry-Berríos, Alvaro and Morel, Mauricio J. and Díaz-Torres, Raúl and Qian, Wenjie and Martinez, Zachary and Mendez, Lois and Perez, Frank and Santoyo, Christy A. and Gimeno-Muñoz, Raquel and Esper, Ronda and Gutierrez, Denisse A. and Varela-Ramirez, Armando and Aguilera, Renato J. and Llano, Manuel and Soler, Monica and Aliaga-Alcalde, Núria and Echegoyen, Luis},
abstractNote = {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.},
doi = {10.1039/c8ra08334g},
journal = {RSC Advances},
number = 73,
volume = 8,
place = {United States},
year = {Thu Dec 13 00:00:00 EST 2018},
month = {Thu Dec 13 00:00:00 EST 2018}
}

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