Fullerenols revisited as stable radical anions

Journal of the American Chemical Society
Lars O HuseboLon J Wilson

Abstract

The first exhaustive purification and characterization of the much-studied "fullerenols", prepared by reaction of C(60) in toluene with an oxygenated, aqueous NaOH solution using tetrabutylammonium hydroxide as a phase transfer catalyst, has been performed. The resulting fullerenol is not simply polyhydroxylated C(60) but rather is a structurally and electronically complex C(60) radical anion with a molecular formula of Na(+)(n)[C(60)O(x)(OH)(y)](n)(-) (where n = 2-3, x = 7-9, and y = 12-15) for three different, but identical, preparations. Surprisingly, Na(+)-fullerenol is paramagnetic, exhibiting mu(B) values in aqueous solution of 1.9-2.1 B.M. at 0.5 T and 300 K and R(1) proton relaxivities of 0.55-0.77 mM(-1)s(-1) at 20 MHz and 40 degrees C, values both slightly higher than those expected for a pure S = 1/2 spin system. ESR studies (ESE-FS and 2D nutation) of frozen aqueous solutions at 1.5 and 5.0 K establish that Na(+)-fullerenol is mainly S = 1/2 with a minor, but significant, component of S = 1. Thus, this is the first report to characterize these widely studied, water-soluble fullerenols as stable radical anions. The stability of the S = 1/2 Na(+)-fullerenol radical is likely due to a highly derivatized C(60) surface t...Continue Reading

References

Jan 1, 1993·Journal of Magnetic Resonance Imaging : JMRI·R E Hendrick, E M Haacke
Apr 29, 1999·Proceedings of the National Academy of Sciences of the United States of America·D W CagleL J Wilson
Oct 24, 2001·The Journal of Organic Chemistry·Hitoshi IikuraEiichi Nakamura
Apr 9, 2002·Bioorganic & Medicinal Chemistry·Kelly A GonzalezGeorge H Nancollas
Nov 22, 1991·Science·P J KrusicK F Preston

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Citations

Sep 16, 2010·Bioconjugate Chemistry·Zhiguo ZhouChristopher L Kepley
Sep 22, 2009·Environmental Science & Technology·Carl W IsaacsonJennifer A Field
Mar 11, 2011·ACS Nano·Roberto B SardenbergJosé M A Figueiredo
Apr 21, 2012·Organic Letters·Wei-Wei ChangXiang Gao
Jan 18, 2014·Journal of the American Chemical Society·Jianyuan ZhangHarry C Dorn
Apr 1, 2008·Nanomedicine·Robert D Bolskar
Oct 5, 2010·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Marion EhrichChris L Kepley
Jun 5, 2015·Analytica Chimica Acta·Alina AstefaneiMaria Teresa Galceran
Jun 19, 2016·Journal of Pharmaceutical Sciences·Daisuke IoharaFumitoshi Hirayama
Sep 13, 2013·Chemistry : a European Journal·Mingming ZhenChunru Wang
Jun 30, 2011·Organic & Biomolecular Chemistry·A G BobylevZ A Podlubnaya
Jul 12, 2013·Beilstein Journal of Organic Chemistry·Mihaela SilionCezar Ungurenasu
Feb 24, 2017·The Journal of Chemical Physics·Sonanki Keshri, B L Tembe
Jul 25, 2014·Chemical Communications : Chem Comm·Yong-Bin SunWei-Guo Song
Dec 21, 2020·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Guilherme S RamosFrédéric Frézard
Sep 2, 2020·Free Radical Biology & Medicine·Jacek GrebowskiGrzegorz Litwinienko
Mar 7, 2009·Organic Letters·Guan-Wu WangZhong-Xiu Chen
Jul 4, 2009·The Journal of Organic Chemistry·Manolis D TzirakisMichael Orfanopoulos
Jan 8, 2009·The Journal of Organic Chemistry·Marta IzquierdoNazario Martín
Nov 15, 2019·Journal of Agricultural and Food Chemistry·Yanjie LiuRui He
Sep 25, 2018·The Journal of Physical Chemistry. a·Zhenzhen WangYuliang Zhao
Jun 16, 2007·Journal of the American Chemical Society·Xinsheng PengIzumi Ichinose
Jul 28, 2005·Journal of the American Chemical Society·Robin Anderson, Andrew R Barron

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