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Exploiting the reversible covalent bonding of boronic acids:Recognition, sensing, and assembly


Reference:

Bull, S.D., Davidson, M.G., Van Den Elsen, J.M.H., Fossey, J.S., Jenkins, A.T.A., Jiang, Y.-B., Kubo, Y., Marken, F., Sakurai, K., Zhao, J. and James, T.D., 2013. Exploiting the reversible covalent bonding of boronic acids:Recognition, sensing, and assembly. Accounts of Chemical Research, 46 (2), pp. 312-326.

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http://dx.doi.org/10.1021/ar300130w

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Abstract

Boronic acids can interact with Lewis bases to generate boronate anions, and they can also bind with diol units to form cyclic boronate esters. Boronic acid based receptor designs originated when Lorand and Edwards used the pH drop observed upon the addition of saccharides to boronic acids to determine their association constants. The inherent acidity of the boronic acid is enhanced when 1,2-, 1,3-, or 1,4-diols react with boronic acids to form cyclic boronic esters (5, 6, or 7 membered rings) in aqueous media, and these interactions form the cornerstone of diol-based receptors used in the construction of sensors and separation systems.In addition, the recognition of saccharides through boronic acid complex (or boronic ester) formation often relies on an interaction between a Lewis acidic boronic acid and a Lewis base (proximal tertiary amine or anion). These properties of boronic acids have led to them being exploited in sensing and separation systems for anions (Lewis bases) and saccharides (diols).The fast and stable bond formation between boronic acids and diols to form boronate esters can serve as the basis for forming reversible molecular assemblies. In spite of the stability of the boronate esters' covalent B-O bonds, their formation is reversible under certain conditions or under the action of certain external stimuli.The reversibility of boronate ester formation and Lewis acid-base interactions has also resulted in the development and use of boronic acids within multicomponent systems. The dynamic covalent functionality of boronic acids with structure-directing potential has led researchers to develop a variety of self-organizing systems including macrocycles, cages, capsules, and polymers.This Account gives an overview of research published about boronic acids over the last 5 years. We hope that this Account will inspire others to continue the work on boronic acids and reversible covalent chemistry.

Details

Item Type Articles
CreatorsBull, S.D., Davidson, M.G., Van Den Elsen, J.M.H., Fossey, J.S., Jenkins, A.T.A., Jiang, Y.-B., Kubo, Y., Marken, F., Sakurai, K., Zhao, J. and James, T.D.
DOI10.1021/ar300130w
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URLURL Type
http://www.scopus.com/inward/record.url?scp=84874051877&partnerID=8YFLogxKUNSPECIFIED
DepartmentsFaculty of Science > Chemistry
Research Centres & Institutes > Institute for Sustainable Energy and the Environment
Faculty of Science > Biology & Biochemistry
Research CentresCentre for Sustainable Chemical Technologies
Centre for Extremophile Research (CER)
RefereedYes
StatusPublished
ID Code34700

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