Boronic acids supramolecular chemistry

Membranes and Molecular Assemblies The Synkinetic Approach 6 Calixarenes Revisited 7 Self-assembly in Supramolecular Systems 8 Anion Receptor Chemistry 9 Boronic Acids in Saccharide Recognition 10 Calixarenes An Introduction, 2nd Edition 11 Polymeric and Self Assembled Hydrogels From Fundamental Understanding to Applications 12 Molecular Logic-based Computation 13 Supramolecular Systems in Biomedical Fields 14 Synthetic Receptors for Biomolecules Design Principles and Applications... 

In applying covalent bond formation in supramolecular chemistry, boronic acids stand out as one of the... 

Because of limited space, this chapter covers porphyrins and expanded porphyrins as receptors through mostly non-covalent or supramolecular interactions. As a general rule, examples wherein the porphyrin acts as a receptor via metal coordination are excluded. For a further reading on this latter topic, the reader is referred to a recent Chemistry Review article entitled Supramolecular Chemistry of Metallopor-phyrins. On the other hand, inspired by a recent review by Anslyn entitled Supramolecular Analytical Chemistry, we expand our definition of receptor-substrate interactions to include certain boronic acid binding motifs and several representative examples of metalated porphyrins that are applied to sensing applications, wherein the proposed mode involves metal complexation. Thus, included in this chapter is a brief summary of the seminal work carried out by Suslick and his group, where porphyrins are used to create the so-called artificial nose, that is, an array-based sensing device for various vapors. Also included are... 

Boronic acids, both alky and aryl, have been available for around 150 years. Currently, the most common method used to prepare boronic acids is the reaction of trialkyl borates with Grignard reagents. While boronic acids are widely used in synthetic chemistry, the aim of this chapter is to introduce the use of boronic acids in molecular recognition and supramolecular chemistry. 

T. D. James, M. D. Phillips, and S. Shinkai, Boronic Acids in Saccharide Recognition (Monographs in Supramolecular Chemistry), Royal Society of Chemistry Cambridge, 2006. 

J. S. Fossey and T. D. James, Boronic Acid-Based Receptor, Supramolecular Chemistry, ed. R A. Gale and J. W. Steed, John Wiley Sons Ltd., Chichester, 2011, vol. 3. 

It should be noted that carbohydrate recognition through formation of boronates has been remarkably successful. However, it involves covalent bonds and cannot be seen as biomimetic. For reviews, see James, T. D., Sandanayake, K. R. A. S. and Shinkai, S. (1996) Saccharide sensing with molecular receptors based on boronic acid, Angew. Chem., Int. Ed. Engl. 35, 1911-1922 Smith, B. D. (1996) Liquid membrane transport using boronic acid carriers, Supramolecular Chemistry 7, 55-60. 

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