Literature DB >> 25843973

Solution-Phase Perfluoroalkylation of C60 Leads to Efficient and Selective Synthesis of Bis-Perfluoroalkylated Fullerenes.

Igor V Kuvychko1, Steven H Strauss1, Olga V Boltalina1.   

Abstract

A solution-phase perfluoroalkylation of C60 with a series of RFI reagents was studied. The effects of molar ratio of the reagents, reaction time, and presence of copper metal promoter on fullerene conversion and product composition were evaluated. Ten aliphatic and aromatic RFI reagents were investigated (CF3I, C2F5I, n-C3F7I, i-C3F7I, n-C4F9I, (CF3)(C2F5)CFI, n-C8F17I, C6F5CF2I, C6F5I, and 1,3-(CF3)2C6F3I) and eight of them (except for C6F5I and 1,3-(CF3)2C6F3I) were found to add the respective RF groups to C60 in solution. Efficient and selective synthesis of C60(RF)2 derivatives was developed.

Entities:  

Keywords:  C60; RFI; fullerene; perfluoroalkyl radicals; perfluoroalkylation

Year:  2012        PMID： 25843973      PMCID： PMC4384446          DOI： 10.1016/j.jfluchem.2012.04.014

Source DB:  PubMed          Journal:  J Fluor Chem        ISSN： 0022-1139            Impact factor:   2.050


  24 in total

1.  Structure, Reactivity, and Chemistry of Fluoroalkyl Radicals.

Authors:  William R. Dolbier
Journal:  Chem Rev       Date:  1996-08-01       Impact factor: 60.622

2.  Redox-tuning endohedral fullerene spin states: from the dication to the trianion radical of Sc(3)N@C(80)(CF(3))(2) in five reversible single-electron steps.

Authors:  Alexey A Popov; Natalia B Shustova; Anna L Svitova; Mary A Mackey; Curtis E Coumbe; J Paige Phillips; Steven Stevenson; Steven H Strauss; Olga V Boltalina; Lothar Dunsch
Journal:  Chemistry       Date:  2010-04-26       Impact factor: 5.236

3.  Synthesis, structure, and 19F NMR spectra of 1,3,7,10,14,17,23,28,31,40-C60(CF3)10.

Authors:  Ivan E Kareev; Igor V Kuvychko; Sergey F Lebedkin; Susie M Miller; Oren P Anderson; Konrad Seppelt; Steven H Strauss; Olga V Boltalina
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

4.  Synthesis, spectroscopic and electrochemical characterization, and DFT study of seventeen C70(CF3)n derivatives (n=2, 4, 6, 8, 10, 12).

Authors:  Alexey A Popov; Ivan E Kareev; Natalia B Shustova; Sergey F Lebedkin; Steven H Strauss; Olga V Boltalina; Lothar Dunsch
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  C1-(C84-C2(11))(CF3)12: trifluoromethylation yields structural proof of a minor C84 cage and reveals a principle of higher fullerene reactivity.

Authors:  Ivan E Kareev; Igor V Kuvychko; Natalia B Shustova; Sergei F Lebedkin; Vyacheslav P Bubnov; Oren P Anderson; Alexey A Popov; Olga V Boltalina; Steven H Strauss
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Isolation and structural X-ray investigation of perfluoroalkyl derivatives of six cage isomers of C84.

Authors:  Nadezhda B Tamm; Lev N Sidorov; Erhard Kemnitz; Sergey I Troyanov
Journal:  Chemistry       Date:  2009-10-12       Impact factor: 5.236

7.  Synthesis, isolation, and addition patterns of trifluoromethylated D5h and I(h) isomers of Sc3N@C80: Sc3N@D5h-C80(CF3)18 and Sc3N@I(h)-C80(CF3)14.

Authors:  Shangfeng Yang; Chuanbao Chen; Mingzhi Jiao; Nadezhda B Tamm; Maria A Lanskikh; Erhard Kemnitz; Sergey I Troyanov
Journal:  Inorg Chem       Date:  2011-03-21       Impact factor: 5.165

8.  Chemical tailoring of fullerene acceptors: synthesis, structures and electrochemical properties of perfluoroisopropylfullerenes.

Authors:  Natalia B Shustova; Igor V Kuvychko; Dmitry V Peryshkov; James B Whitaker; Bryon W Larson; Yu-Sheng Chen; Lothar Dunsch; Konrad Seppelt; Alexey A Popov; Steven H Strauss; Olga V Boltalina
Journal:  Chem Commun (Camb)       Date:  2010-11-09       Impact factor: 6.222

9.  Synthesis and X-ray or NMR/DFT structure elucidation of twenty-one new trifluoromethyl derivatives of soluble cage isomers of C76, C78, C84, and C90.

Authors:  Ivan E Kareev; Alexey A Popov; Igor V Kuvychko; Natalia B Shustova; Sergey F Lebedkin; Vyachevslav P Bubnov; Oren P Anderson; Konrad Seppelt; Steven H Strauss; Olga V Boltalina
Journal:  J Am Chem Soc       Date:  2008-09-13       Impact factor: 15.419

10.  Production of perfluoroalkylated nanospheres from buckminsterfullerene.

Authors:  P J Fagan; P J Krusic; C N McEwen; J Lazar; D H Parkert; N Herron; E Wasserman
Journal:  Science       Date:  1993-10-15       Impact factor: 47.728
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