Self-assembly of a “double dynamic covalent” amphiphile featuring a glucose-responsive imine bond

There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

Abstract

Glucose recognition via in situ formation of supramolecular vesicular aggregates that involve two dynamic covalent bonds.

Abstract

Glucose binding via boronate ester linkages selectively triggers imine bond formation between 4-formylphenylboronic acid and octylamine, leading to the formation of vesicular aggregates in aqueous solutions. This “double dynamic covalent assembly” allows the facile selective sensing of glucose against the otherwise serious interferant fructose, without the need to resort to synthetic effort.

Related collections

Most cited references 25

Record: found
Abstract: found
Article: not found

Dynamic imine chemistry.

Matthew E Belowich, J Fraser Stoddart (2012)

Formation of an imine--from an amine and an aldehyde--is a reversible reaction which operates under thermodynamic control such that the formation of kinetically competitive intermediates are, in the fullness of time, replaced by the thermodynamically most stable product(s). For this fundamental reason, the imine bond has emerged as an extraordinarily diverse and useful one in the hands of synthetic chemists. Imine bond formation is one of a handful of reactions which define a discipline known as dynamic covalent chemistry (DCC), which is now employed widely in the construction of exotic molecules and extended structures on account of the inherent 'proof-reading' and 'error-checking' associated with these reversible reactions. While both supramolecular chemistry and DCC operate under the regime of reversibility, DCC has the added advantage of constructing robust molecules on account of the formation of covalent bonds rather than fragile supermolecules resulting from noncovalent bonding interactions. On the other hand, these products tend to require more time to form--sometimes days or even months--but their formation can often be catalysed. In this manner, highly symmetrical molecules and extended structures can be prepared from relatively simple precursors. When DCC is utilised in conjunction with template-directed protocols--which rely on the use of noncovalent bonding interactions between molecular building blocks in order to preorganise them into certain relative geometries as a prelude to the formation of covalent bonds under equilibrium control--an additional level of control of structure and topology arises which offers a disarmingly simple way of constructing mechanically-interlocked molecules, such as rotaxanes, catenanes, Borromean rings, and Solomon knots. This tutorial review focuses on the use of dynamic imine bonds in the construction of compounds and products formed with and without the aid of additional templates. While synthesis under thermodynamic control is giving the field of chemical topology a new lease of life, it is also providing access to an endless array of new materials that are, in many circumstances, simply not accessible using more traditional synthetic methodologies where kinetic control rules the roost. One of the most endearing qualities of chemistry is its ability to reinvent itself in order to create its own object, as Berthelot first pointed out a century and a half ago.

0 comments Cited 265 times – based on 0 reviews      Review now

Bookmark

Record: found
Abstract: not found
Article: not found

The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears

Jun Yan, Greg Springsteen, Susan Deeter … (2004)

0 comments Cited 129 times – based on 0 reviews      Review now

Bookmark

Record: found
Abstract: found
Article: not found

Specific detection of D-glucose by a tetraphenylethene-based fluorescent sensor.

Li Li, Chih-Yi Liu, Jane C. Deng … (2011)

A conceptually new "light-up" biosensor with a high specificity for d-glucose (Glu) in aqueous media has been developed. The emission from a tetraphenylethene (TPE)-cored diboronic acid (1) was greatly boosted when the fluorogen was oligomerized with Glu because of restriction of the intramolecular rotations of the aryl rotors of TPE by formation of the oligomer. Little change in the light emission was observed when 1 was mixed with D-fructose, D-galactose, or D-mannose, as these saccharides are unable to oligomerize with the fluorogen.

0 comments Cited 129 times – based on 0 reviews      Review now

Bookmark

All references

Author and article information

Journal

Journal ID (publisher-id): CHCOFS

Title: Chemical Communications

Abbreviated Title: Chem. Commun.

Publisher: Royal Society of Chemistry (RSC)

ISSN (Print): 1359-7345

ISSN (Electronic): 1364-548X

Publication date Created: 2016

Publication date (Print): 2016

Volume: 52

Issue: 43

Pages: 6981-6984

Article

DOI: 10.1039/C6CC03167F

SO-VID: cf1c3274-cabe-49e1-842c-62c5c0d2ad0c

History

Data availability:

Comments

Comment on this article

scite_

Smart Citations

Citing PublicationsSupportingMentioningContrasting

View Citations

See how this article has been cited at scite.ai

scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.