Binding Behaviors of p-Sulfonatocalix[4]arene with Gemini Guests
- 5 February 2013
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Physical Chemistry B
- Vol. 117 (6), 1978-1987
- https://doi.org/10.1021/jp312744d
Abstract
A dozen of homoditopic cations, possessing different spacer lengths and rigidities, as well as sizes, shapes, and charges of terminal groups, were synthesized as candidate gemini guests for the complexation of p-sulfonatocalix[4]arenes (SC4A). The 12 gemini guests are divided into five species according to the different terminal groups: imidazolium (G1–G3), pyridinium (G4–G6), quinolinium (G7), viologen (G8–G11), and 1,4-diazabicyclo[2.2.2]octane (DBO, G12). Their binding structures and stoichiometries with SC4A were examined by NMR spectroscopy, which is helpful to construct diverse highly ordered assemblies. The obtained results show that the length of the linkers, as well as the charge numbers on the end groups have a pronounced effect on the binding stoichiometry, whereas the size and shape of the terminal groups have no significant influence. Furthermore, both the stability constants and thermodynamic parameters of SC4A with the terminal subunits were determined by the isothermal titration calorimetry experiments, which are valuable to understand the binding behavior, giving quantitatively deep insight.Keywords
This publication has 100 references indexed in Scilit:
- Cucurbituril‐Modulated Supramolecular Assemblies: From Cyclic Oligomers to Linear PolymersChemistry – A European Journal, 2012
- Calixarene-Based Surfactants: Evidence of Structural Reorganization upon MicellizationLangmuir, 2012
- Multistimuli Responsive Supramolecular Vesicles Based on the Recognition of p-Sulfonatocalixarene and its Controllable Release of DoxorubicinACS Nano, 2011
- Sulfonated Calix[6]arene Host–Guest Complexes Induce Surfactant Self‐AssemblyChemistry – A European Journal, 2009
- Nano‐Supramolecular Assemblies Constructed from Water‐Soluble Bis(calix[5]arenes) with Porphyrins and Their Photoinduced Electron Transfer PropertiesChemistry – An Asian Journal, 2009
- Calix[n]arene sulfonic acids bearing pendant aliphatic chains as recyclable surfactant-type Brønsted acid catalysts for allylic alkylation with allyl alcohols in waterGreen Chemistry, 2008
- Templating photodimerization of stilbazoles with water-soluble calixarenesPhotochemical & Photobiological Sciences, 2006
- Intermolecular complexation thermodynamics between water-soluble calix[4]arenes and diazacycloalkanesThermochimica Acta, 2005
- Microcalorimetric titration of a tetra-p-sulphonated calix[4]arene with α,ω-alkyl diammonium ions in an aqueous solutionThermochimica Acta, 1998
- Water-soluble calix[6]arenes. Characterization of 5,11,17,23,29,35-hexasulphonate-37,38,39,40,41,42-hexahydroxycalix[6]arene and thermodynamic study of proton complex formationThermochimica Acta, 1995