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2011
Ménard-Moyon Cécilia, Fabbro Chiara, Prato Maurizio, Bianco Alberto
One-pot triple functionalization of carbon nanotubes Journal Article
In: Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 11, pp. 3222–3227, 2011, ISSN: 1521-3765.
Abstract | Links | BibTeX | Tags: Aniline Compounds, Azo Compounds, Benzylamines, carbon, I2CT, Nanotubes, Raman, Spectrophotometry, Spectrum Analysis, Surface Properties, Team-Bianco
@article{menard-moyon_one-pot_2011,
title = {One-pot triple functionalization of carbon nanotubes},
author = {Cécilia Ménard-Moyon and Chiara Fabbro and Maurizio Prato and Alberto Bianco},
doi = {10.1002/chem.201003050},
issn = {1521-3765},
year = {2011},
date = {2011-03-01},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
volume = {17},
number = {11},
pages = {3222--3227},
abstract = {Carbon nanotubes (CNTs) are very promising as carriers for the delivery of bioactive molecules. The multifunctionalization of CNTs is necessary to impart multimodalities for the development of future CNT-based multipotent therapeutic constructs. In this context, we report the first example of covalent trifunctionalization of different types of CNTs. Our strategy is a simple and efficient methodology based on the simultaneous functionalization of the nanotube surface with three different active groups. The reaction is performed in one step by arylation with diazonium salts generated in situ. The CNTs are functionalized with benzylamine moieties blocked with three different protecting groups that can be selectively removed under specific conditions. The trifunctionalized CNTs were characterized by TEM, thermogravimetric analysis, and Raman and UV/Vis/NIR spectroscopy, while the amine loading was determined by using the Kaiser test. The sequential removal of the protecting groups of the amine functions allows the grafting of the molecules of interest on the nanotube surface to be controlled.},
keywords = {Aniline Compounds, Azo Compounds, Benzylamines, carbon, I2CT, Nanotubes, Raman, Spectrophotometry, Spectrum Analysis, Surface Properties, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Carbon nanotubes (CNTs) are very promising as carriers for the delivery of bioactive molecules. The multifunctionalization of CNTs is necessary to impart multimodalities for the development of future CNT-based multipotent therapeutic constructs. In this context, we report the first example of covalent trifunctionalization of different types of CNTs. Our strategy is a simple and efficient methodology based on the simultaneous functionalization of the nanotube surface with three different active groups. The reaction is performed in one step by arylation with diazonium salts generated in situ. The CNTs are functionalized with benzylamine moieties blocked with three different protecting groups that can be selectively removed under specific conditions. The trifunctionalized CNTs were characterized by TEM, thermogravimetric analysis, and Raman and UV/Vis/NIR spectroscopy, while the amine loading was determined by using the Kaiser test. The sequential removal of the protecting groups of the amine functions allows the grafting of the molecules of interest on the nanotube surface to be controlled.
2009
Singh Prabhpreet, Campidelli Stéphane, Giordani Silvia, Bonifazi Davide, Bianco Alberto, Prato Maurizio
Organic functionalisation and characterisation of single-walled carbon nanotubes Journal Article
In: Chemical Society Reviews, vol. 38, no. 8, pp. 2214–2230, 2009, ISSN: 1460-4744.
Abstract | Links | BibTeX | Tags: Alkylation, carbon, Esterification, Free Radicals, Halogenation, I2CT, Microscopy, Nanotubes, Oxidation-Reduction, Spectrum Analysis, Team-Bianco
@article{singh_organic_2009,
title = {Organic functionalisation and characterisation of single-walled carbon nanotubes},
author = {Prabhpreet Singh and Stéphane Campidelli and Silvia Giordani and Davide Bonifazi and Alberto Bianco and Maurizio Prato},
doi = {10.1039/b518111a},
issn = {1460-4744},
year = {2009},
date = {2009-08-01},
journal = {Chemical Society Reviews},
volume = {38},
number = {8},
pages = {2214--2230},
abstract = {Since carbon nanotubes (CNTs) display unique structures and remarkable physical properties, a variety of applications have emerged in both materials and life sciences. In terms of applications, the functionalisation of nanotubes is extremely important, as it increases their solubility and processability, and combines the unique properties of single-walled carbon nanotubes (SWCNTs) with those of other classes of materials. A number of methods have been developed, which can be divided into two major approaches: (1) non-covalent supramolecular modifications, and (2) covalent functionalisation. In this tutorial review, we survey the covalent modification of SWCNTs with organic moieties, and illustrate the major analytical techniques routinely used to characterise the functionalised materials.},
keywords = {Alkylation, carbon, Esterification, Free Radicals, Halogenation, I2CT, Microscopy, Nanotubes, Oxidation-Reduction, Spectrum Analysis, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Since carbon nanotubes (CNTs) display unique structures and remarkable physical properties, a variety of applications have emerged in both materials and life sciences. In terms of applications, the functionalisation of nanotubes is extremely important, as it increases their solubility and processability, and combines the unique properties of single-walled carbon nanotubes (SWCNTs) with those of other classes of materials. A number of methods have been developed, which can be divided into two major approaches: (1) non-covalent supramolecular modifications, and (2) covalent functionalisation. In this tutorial review, we survey the covalent modification of SWCNTs with organic moieties, and illustrate the major analytical techniques routinely used to characterise the functionalised materials.
2006
Brough Peter, Klumpp Cedric, Bianco Alberto, Campidelli Stephane, Prato Maurizio
[60]fullerene-pyrrolidine-N-oxides Journal Article
In: The Journal of Organic Chemistry, vol. 71, no. 5, pp. 2014–2020, 2006, ISSN: 0022-3263.
Abstract | Links | BibTeX | Tags: Chromatography, Fullerenes, High Pressure Liquid, I2CT, Nitrogen, Oxidation-Reduction, Oxides, Pyrrolidines, Spectrum Analysis, Team-Bianco
@article{brough_60fullerene-pyrrolidine-n-oxides_2006,
title = {[60]fullerene-pyrrolidine-N-oxides},
author = {Peter Brough and Cedric Klumpp and Alberto Bianco and Stephane Campidelli and Maurizio Prato},
doi = {10.1021/jo052388s},
issn = {0022-3263},
year = {2006},
date = {2006-03-01},
journal = {The Journal of Organic Chemistry},
volume = {71},
number = {5},
pages = {2014--2020},
abstract = {Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The 1H NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a 15N isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.},
keywords = {Chromatography, Fullerenes, High Pressure Liquid, I2CT, Nitrogen, Oxidation-Reduction, Oxides, Pyrrolidines, Spectrum Analysis, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The 1H NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a 15N isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.
