A new open benzodipyrrole-based chemosensor for hydrogenpyrophosphate anion in aqueous environment

Neutral anion receptors working in highly demanding solvents are new materials being sought. Benzopyrroles are more acidic than amides and pyrrole itself, and are promising building blocks in the design of host compounds. A whole series of receptors based upon benzopyrroles were synthesized and evaluated. They include carbazole, dipyrrolonaphthalene, and 7-aminoindole-based hosts. Most of them demonstrate moderate binding affinities in dimethyl sulfoxide (DMSO) and have good selectivity toward tetrahedral oxyanions. Recently, a group of receptors utilizing 7-aminoindole and urea moieties proved to work in a very competitive solvent-methanol.

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“…One of them, appended with amido-pyrrolic side arms, showed potent anion binding properties, especially toward pyrrophosphate anions [15]. …”

Section: Dipyrrolonaphthalenesmentioning

confidence: 99%

Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Jurczak

Chmielewski

Dydio

et al. 2011

Pure and Applied Chemistry

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“…14 The benzodipyrrole derived receptor 6 was shown to possess good selectivity for HP 2 O 7 3À in 5% water-acetone-d 6 (HP 2 O 7 3À C6: K a = 9081 M À1 ). 15 Molecular modelling indicated that complex formation involves a tight network of hydrogen bonds between the donors of 6 and oxygen atoms of the substrate. Very high anion affinity was observed for receptors 7a and 7b that combine indole and urea subunits.…”

Section: Anion Recognition In Solvent Mixtures Containing O30% Of Watermentioning

confidence: 99%

Anion recognition in water

2010

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Anion recognition by synthetic receptors in water is not a new field, indeed the first receptors that were shown to interact with anionic species exhibited high affinity in aqueous solutions. Anion recognition in aqueous solution was, however, for a long time the domain of receptors containing multiple positive charges and/or metal ions while interactions of neutral receptors with anions were believed to be too weak to be efficient in water. Independent work in several groups has recently shown that this assumption is not necessarily correct. As a consequence, a much wider range of receptors is now available with which anion recognition in competitive aqueous media can be achieved. This tutorial review presents selected examples of synthetic anion receptors active in aqueous solutions and guidelines to achieve anion recognition in water.

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“…57) against anions was studied in acetone-water (5% v/v) solutions. 185 145 displays an emission band at 500 nm whose intensity was enhanced selectively in the presence of HP 2 O 7 3À whereas the addition of AcO À , BzO À and H 2 PO 4 À induced negligible changes. The authors suggest that 145 has a pre-organised cavity that was able to accommodate selectively the HP 2 O 7 3À anion through the formation of several hydrogen bonds with the N-H moieties.…”

Section: àmentioning

confidence: 99%

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

2011

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A new open benzodipyrrole-based chemosensor for hydrogenpyrophosphate anion in aqueous environment

Abstract: Benzodipyrrolic derivatives have been synthesised and evaluated as neutral receptors for anions, in a mixed acetone-water media.

Cited by 35 publications

References 45 publications

Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Anion recognition in water

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

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