Journal article

Publication year: 2012

Pages: 4524-4530

Journal: Organic & Biomolecular Chemistry

Volume number: 10

Issue number: 23

DOI Link: https://doi.org/10.1039/C2OB06915F

Publisher: Royal Society of Chemistry

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 (K_a, ΔH, ΔG and ΔS) for the host–guest inclusion. The stoichiometry of the complexes is invariably 1 : 1. It was found that K_a, 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, K_a = 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.

Harvard Citation style: Voskuhl, J., Waller, M., Bandaru, S., Tkachenko, B., Fregonese, C., Wibbeling, B., et al. (2012) Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes, Organic and Biomolecular Chemistry, 10(23), pp. 4524-4530. https://doi.org/10.1039/C2OB06915F

APA Citation style: Voskuhl, J., Waller, M., Bandaru, S., Tkachenko, B., Fregonese, C., Wibbeling, B., Schreiner, P., & Ravoo, B. (2012). Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes. Organic and Biomolecular Chemistry. 10(23), 4524-4530. https://doi.org/10.1039/C2OB06915F