Issue 23, 2012

Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes

Abstract

We report on the noncovalent interactions of nanodiamond carboxylic acids derived from adamantane, diamantane, and triamantane with β- and γ-cyclodextrins. The water solubility of the nanodiamonds was increased by attaching an aromatic dicarboxylic acid via peptide coupling. Isothermal titration calorimetry experiments were performed to determine the thermodynamic parameters (Ka, ΔH, ΔG and ΔS) for the host–guest inclusion. The stoichiometry of the complexes is invariably 1 : 1. It was found that Ka, ΔG and ΔH of inclusion increase for larger nanodiamonds. ΔS is generally positive, in particular for the largest nanodiamonds. β-Cyclodextrin binds all nanodiamonds, γ-cyclodextrin clearly prefers the most bulky nanodiamonds. The interaction of 9-triamantane carboxylic acid shows one of the strongest complexation constants towards γ-cyclodextrin ever reported, Ka = 5.0 × 105 M−1. In order to gain some insight into the possible structural basis of these inclusion complexes we performed density functional calculations at the B97-D3/def2-TZVPP level of theory.

Graphical abstract: Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes

Supplementary files

Article information

Article type
Paper
Submitted
13 Nov 2011
Accepted
01 Mar 2012
First published
02 Mar 2012

Org. Biomol. Chem., 2012,10, 4524-4530

Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes

J. Voskuhl, M. Waller, S. Bandaru, B. A. Tkachenko, C. Fregonese, B. Wibbeling, P. R. Schreiner and B. J. Ravoo, Org. Biomol. Chem., 2012, 10, 4524 DOI: 10.1039/C2OB06915F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements