Covalent Grafting of BPin functions on Carbon Nanotubes and Chan–Lam–Evans Post‐Functionalization. Issue 6 (18th December 2018)

• Record Type: Journal Article
• Authors: Desmecht, Antonin; Sheet, Debobrata; Poleunis, Claude; Hermans, Sophie; Riant, Olivier
• Is Part Of: Chemistry. Volume 25:Issue 6(2019)
• Page Start: 1436
• Page End: 1440
• Publication Date: 2018-12-18
• Subjects: carbon nanotubes -- Chan–Lam–Evans coupling -- materials science -- organoboron compounds -- ToF-SIMS; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804859
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The chemical functionalization of carbon nanotubes is often a prerequisite prior to their use in various applications. The covalent grafting of 4, 4, 5, 5‐tetramethyl‐1, 3, 2‐dioxaborolane (BPin) functional groups directly on the surface of multi‐ and single‐walled carbon nanotubes, activated by nucleophilic addition of n BuLi, was carried out. Thermogravimetric analysis (TGA) coupled with mass spectrometry, Raman spectroscopy, X‐ray photoelectron spectroscopy (XPS) and time‐of‐flight secondary ions mass spectrometry (ToF‐SIMS) confirmed the efficiency of this methodology and proved the integrity and covalent grafting of the BPin functional groups. These groups were further reacted with various nucleophiles in the presence of a copper(II) source in the conditions of the aerobic Chan–Lam–Evans coupling. The resulting materials were characterized by TGA, XPS and ToF‐SIMS. This route is efficient, reliable and among the scarce reactions that enable the direct grafting of heteroatoms at carbonaceous material surfaces. Abstract : Boron on CNTs : The first direct grafting of boron‐based groups on carbon nanotubes (CNTs) through a two‐step nucleophilic addition and boronic acid pinacol ester (BPin)‐capture reaction is reported. The grafted BPin groups were afterwards replaced by different O‐ and N‐based nucleophiles through the copper‐catalyzed Chan–Lam–Evans coupling.