thermodynamic stability of hydrogen-bonded nanostructures: a calorimetric study

M.G.J. ten Cate, Jurriaan Huskens, Mercedes Crego Calama, David Reinhoudt

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31 Citations (Scopus)

Abstract

The self-assembly of hydrogen-bonded aggregates (rosettes) in solvent mixtures of different polarity has been studied by calorimetry. The C50 parameter, the concentration when 50 % of the components are incorporated in the assembly, is used to compare assemblies with different stoichiometry. C50 for the single rosette 13(BuCYA)3 (1=N,N-di(4-tert-butylphenyl)melamine; BuCYA=n-butylcyanuric acid) in 1,2-dichloroethane is 25 µM, whereas for double rosettes 2 a3(BuCYA)6 and 2 b3(BuCYA) (2=calix[4]arene-dimelamine) it is 0.7 and 7.1 M, respectively. ΔG°, ΔH°, and TΔS° values indicate that the thermodynamics of double rosettes reflect the independent assembly of two individual single rosette structures or two rosettes reinforced by additional stabilizing interactions. In more polar solvents the stability of double rosettes decreases. From the correlation of ΔG° with solvent polarity it is predicted that it should be possible to assemble double rosettes in methanol or water. The assembly of 2 b3(BuCYA)6 in 100 % MeOH was proven by 1H NMR and CD spectroscopy
Original languageUndefined
Pages (from-to)3632-3639
Number of pages8
JournalChemistry: a European journal
Volume10
Issue number15
DOIs
Publication statusPublished - 2004

Keywords

  • Hydrogen bonds
  • Calorimetry
  • polar solvents
  • IR-49558
  • Self-Assembly
  • METIS-222164
  • Thermodynamics

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