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Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation

Many applications of carbon nanotubes require their chemical functionalization. Both covalent and supramolecular approaches have been extensively investigated. A less trodden path is the combination of both covalent and noncovalent chemistries, where the formation of covalent bonds triggers a partic...

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Autores principales: Leret, Sofía, Pouillon, Yann, Casado, Santiago, Navío, Cristina, Rubio, Ángel, Pérez, Emilio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5364655/
https://www.ncbi.nlm.nih.gov/pubmed/28451307
http://dx.doi.org/10.1039/c6sc03894h
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author Leret, Sofía
Pouillon, Yann
Casado, Santiago
Navío, Cristina
Rubio, Ángel
Pérez, Emilio M.
author_facet Leret, Sofía
Pouillon, Yann
Casado, Santiago
Navío, Cristina
Rubio, Ángel
Pérez, Emilio M.
author_sort Leret, Sofía
collection PubMed
description Many applications of carbon nanotubes require their chemical functionalization. Both covalent and supramolecular approaches have been extensively investigated. A less trodden path is the combination of both covalent and noncovalent chemistries, where the formation of covalent bonds triggers a particularly stable noncovalent interaction with the nanotubes. We describe a series of naphthalene diimide (NDI) bisalkene molecules that, upon mixing with single-walled carbon nanotubes (SWNTs) and Grubbs' catalyst, undergo two different reaction pathways. On one hand, they ring-close around the SWNTs to form rotaxane-like mechanically interlocked derivatives of SWNTs (MINTs). Alternatively, they oligomerize and then wrap around the SWNTs. The balance of MINTs to oligomer-wrapped SWNTs depends on the affinity of the NDI molecules for the SWNTs and the kinetics of the metathesis reactions, which can be controlled by varying the solvent. Thorough characterization of the products (TGA, TEM, AFM, Raman, UV-vis-NIR, PLE, XPS and UPS) confirms their structure and shows that each type of functionalization affects the electronic properties of the SWNTs differently.
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spelling pubmed-53646552017-04-27 Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation Leret, Sofía Pouillon, Yann Casado, Santiago Navío, Cristina Rubio, Ángel Pérez, Emilio M. Chem Sci Chemistry Many applications of carbon nanotubes require their chemical functionalization. Both covalent and supramolecular approaches have been extensively investigated. A less trodden path is the combination of both covalent and noncovalent chemistries, where the formation of covalent bonds triggers a particularly stable noncovalent interaction with the nanotubes. We describe a series of naphthalene diimide (NDI) bisalkene molecules that, upon mixing with single-walled carbon nanotubes (SWNTs) and Grubbs' catalyst, undergo two different reaction pathways. On one hand, they ring-close around the SWNTs to form rotaxane-like mechanically interlocked derivatives of SWNTs (MINTs). Alternatively, they oligomerize and then wrap around the SWNTs. The balance of MINTs to oligomer-wrapped SWNTs depends on the affinity of the NDI molecules for the SWNTs and the kinetics of the metathesis reactions, which can be controlled by varying the solvent. Thorough characterization of the products (TGA, TEM, AFM, Raman, UV-vis-NIR, PLE, XPS and UPS) confirms their structure and shows that each type of functionalization affects the electronic properties of the SWNTs differently. Royal Society of Chemistry 2017-03-01 2016-11-04 /pmc/articles/PMC5364655/ /pubmed/28451307 http://dx.doi.org/10.1039/c6sc03894h Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by-nc/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/ (https://creativecommons.org/licenses/by-nc/3.0/) ) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Leret, Sofía
Pouillon, Yann
Casado, Santiago
Navío, Cristina
Rubio, Ángel
Pérez, Emilio M.
Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title_full Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title_fullStr Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title_full_unstemmed Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title_short Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
title_sort bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5364655/
https://www.ncbi.nlm.nih.gov/pubmed/28451307
http://dx.doi.org/10.1039/c6sc03894h
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