Catching Fullerenes: Synthesis of Molecular Nanogloves

06 November 2024, Version 1

Abstract

Herein, we report the synthesis of a new series of rigid, all meta-phenylene, conjugated deep-cavity molecules, displaying high binding affinity towards buckyballs. A facile two-step synthetic approach with an overall yield of approximately 54% has been developed using a templating strategy that combines the general structure of resorcin[4]arene and [12]cyclo-meta-phenylene. These two moieties are covalently linked via four acetal bonds resulting in a glove-like architecture. 1H NMR titration experiments reveal fullerene binding affinities (Ka) ex-ceeding >10^6 M–1. The size complementarity between fullerenes and these scaffolds maximizes CH⋯π and π⋯π interactions and their host:guest adduct resemble a ball in a glove, hence their name as nanogloves. Fullerene recognition is tested by suspending carbon soot in a solution of nanoglove in 1,1,2,2-tetrachloroethane, where more than a dozen fullerenes are observed ranging from C60 to C96.

Keywords

Molecular recognition
Hos:guest chemistry
Supramolecular architectures

Supplementary materials

Title
Description
Actions
Title
Supplementary Information
Description
Experimental details, materials and methods including DFT calculations, single-crystal X-ray diffraction data, multinuclear NMR spectra, light absorption and emission spectra, and MS data.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.