One‐Pot Triple Functionalization of Carbon Nanotubes

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.

Carbon based substrates for interfacing neurons: Comparing pristine with functionalized carbon nanotubes effects on cultured neuronal networks

“…1a) [15,16], and (b) the radical diazonium salt arylation of MWNTs using a substituted aniline and isoamyl nitrite as shown on Fig. 1b [17].…”

“…To further explore the impact of functionalized CNT scaffolds on neuronal networks, and to improve the versatility of the materials used, we here report the effects of two kinds of covalently modified MWNTs on neuronal communication. In particular we have chosen two well known chemical approaches like 1,3-dipolar cycloaddition of azomethine ylides [15,16] and the radical diazonium salt arylation [17].…”

Controlled Chemical Derivatisation of Carbon Nanotubes with Imaging, Targeting, and Therapeutic Capabilities

“…Concomitantly, oxygenated functions, mainly carboxylic acids, were generated, leading to an enhanced aqueous dispersibility. The triple‐ functionalised MWCNTs ( f ‐MWCNTs) 5 bearing protected amines were prepared according to our previous strategy (Scheme ) 16…”

“…One advantage of CNTs is their high aspect ratio that allows multi‐functionalisation with different molecules that have specific properties or functionalities 15. In this context, a few years ago we developed an original one‐pot process for the triple functionalisation of pristine and oxidised single‐ and multi‐walled CNTs (SWCNTs and MWCNTs) 16. This straightforward approach was based on the simultaneous reaction of three different diazonium salts generated in situ from the corresponding anilines.…”

Multifunctionalized carbon nanotubes as advanced multimodal nanomaterials for biomedical applications

“…This multimodal tracking approach allowed assessing a rapid and effective CNT elimination from the blood circulation by the kidney without concomitant degradation. Recently, our group described a simple, effi cient and well-controlled approach based on a one-pot process for the covalent functionalization of CNTs with three different functional groups [70] . Our strategy relies on the simultaneous reaction of a mixture of three aryldiazonium salts generated in situ , leading to arylation of the nanotube surface ( Figure 4 , Approach B).…”