Inclusion of potassium 4,4 '-biphenyldicarboxylate into beta-cyclodextrin: the design and synthesis of an organic secondary building unit
authors Fernandes, JA; Paz, FAA; Braga, SS; Ribeiro-Claro, PJA; Rocha, J
nationality International
journal NEW JOURNAL OF CHEMISTRY
keywords COORDINATION POLYMERS; INDUSTRIAL APPLICATIONS; COMPLEX-FORMATION; DRUG-DELIVERY; RETICULAR SYNTHESIS; FRAMEWORK MATERIALS; SOLID-STATE; NETWORK; ACID; MOFS
abstract The paper describes a design strategy for the preparation of a novel inclusion compound (potassium 4,4 '-biphenyldicarboxylate subset of beta-CD) suitable for use in supramolecular chemistry. In the first step the chemical feasibility of such an inclusion compound was evaluated by DFT calculations. Preliminary results revealed that two types of adducts are energetically favourable: 1 : 1 and 2 : 1 (host : guest). The stability in aqueous solution of the prepared inclusion compounds, a strict requirement for their use as Secondary Building Units in supramolecular chemistry, was investigated by means of liquid NMR (Job plot) and computational resolution of the equilibrium equations. As predicted by the theoretical calculations, it was found that two types of inclusion compounds were formed. The 1 : 1 adduct has a large formation constant. Synthesis led to the preparation of two unusual crystalline products depending on the pH. Compound 1 (formed at pH = 7.5) is truly unprecedented and comprises a 1 : 1 inclusion compound with a large water layer. Because it is highly stable in the liquid state this novel inclusion compound is a good candidate to be employed as a rigid organic Secondary Building Units in the construction of modular coordination polymers. Compound 2 (formed at pH = 10) comprises a mixture of the same two adducts predicted by the theoretical calculations and detected by liquid NMR, and its crystal structure exhibits a rare proportion between the host and the guest (4 : 3).
publisher ROYAL SOC CHEMISTRY
issn 1144-0546
year published 2011
volume 35
issue 6
beginning page 1280
ending page 1290
digital object identifier (doi) 10.1039/c0nj00796j
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000291112900019
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journal analysis (jcr 2017):
journal impact factor 3.201
5 year journal impact factor 3.181
category normalized journal impact factor percentile 62.281
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