Non-covalent functionalization of single walled carbon nanotubes with pyrene pendant polyester: A DFT supported study

Non-covalent attachment onto single-walled carbon nanotubes (SWCNTs) by protecting nanotubes’ intrinsic properties has an important role in development of hybrid composite materials. Herein, we present non-covalent functionalization of SWCNTs with pyrene-containing novel polyester. The preparation of polyester involving electron deficient internal alkyne units was achieved by an esterification reaction between acetylene dicarboxylic acid and 1,4-butandiol. Subsequently, pyren-1-ylmethyl 3-azidopropanoate was incorporated into the polyester via the 1,3-dipolar cycloaddition reaction at a moderately low temperature in 1,4-dioxane yielding pyrene-pendant polyester (PE-Py). Finally, PE-Py was physically loaded on SWCNTs under mild conditions at ambient temperature. Characterization processes were thoroughly carried out by 1H NMR, GPC, TGA, FT-IR and HR-TEM analyses for both polymer and modified-SWCNTs. In this work we report the first theoretical study of the physically adsorption of pyrene-pendant polyesters on SWCNTs using density functional theory (DFT) calculations to support experimental results. Our study is promising to combine both experimental and theoretical study on SWCNTs’ functionalization. •Characterization of pyrene containing polyester and modified nanotubes with 1H NMR, GPC, TGA, FT-IR and HRTEM analyses.•Strong π-π stacking interactions between pyrene-pendant polyester containing electron deficient internal alkyne units derived from acetylene dicarboxylic acid.•Adsorption energy via π-π stacking interaction was calculated with M06–2X/6-31G(d) level of theory after eliminating the basis set superposition errors.