Evaluating the reactivity superiority of two different single-walled carbon nanotube anions using an anhydride electrophile

Official URL: http://www.hjbc.hacettepe.edu.tr/journal/volume-47/issue-1/evaluating-the-reactivity-superiority-of-two-different-single-walled-carbon-nanotube-anions-using-an-anhydride-electrophile/

Reductive chemistries have widely been used to functionalize single-walled carbon nanotubes (SWCNTs). However, the reactivity of negatively charged SWCNTs (NC-SWCNTs), prepared by different reductive chemistries, to the same electrophilic reagent has not been evaluated. Here in, the first example of the reactivity comparison of two different NC-SWCNTs towards 3-nitrophthalic anhydride is presented, and two novel functionalized SWCNTs are synthesized and characterized. The NC-SWCNTs, that are denoted as [(nBu―SWCNTn)-• Lin+] and [SWCNTn-• Lin+], are prepared via n-butyl lithium and lithium naphthalenide addition, respectively, and are reacted by 3-nitrophthalic anhydride under dry conditions. The resulting functionalized SWCNTs are characterized by Raman, UV-vis-NIR, TGA-MS, XPS, and TEM. The reactivity of [(nBu―SWCNTn)-• Lin+] towards electrophilic 3-nitrophthalic anhydride is found to be higher than [SWCNTn-• Lin+]. This is probably due to the high nucleophilic character of [(nBu―SWCNTn)-• Lin+] which bears lone pair electrons and electrondonating butyl groups.