Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Jurczak, Janusz; Chmielewski, Michał J.; Dydio, Paweł; Lichosyt, Dawid; Ulatowski, Filip; Zieliński, Tomasz

doi:10.1351/pac-con-10-11-11

Cited by 11 publications

(5 citation statements)

References 24 publications

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“…In order to provide further justification that anion binding affinities of simple receptors are correlated with their position in the Hofmeister series we performed quantum mechanical calculations of interactions of these anions with pyrrole which we have chosen as a model single H-bond donor lacking any preference on shape and size of the guest (see ESI † for details). 13 Calculated interaction energies of its complexes with anions are consistent with the Hofmeister bias, i.e. more basic anions are bound more strongly by this putatively simple…”

Section: Resultssupporting

confidence: 53%

Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

et al. 2017

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The binding selectivity of structurally simple anion receptors is governed by the Hofmeister series (SO > HPO > carboxylates ∼ HPO > HCO > Cl), and exceptions to this rule are rare and require utilization of structurally sophisticated receptors. In this paper we examined a set of 48 structurally diverse anion receptors, barely one fourth of which exhibit selectivity for chloride over more basic dihydrogen phosphate (HPO) or carboxylates (MeCO and PhCO). Searching for regularities in the properties of these mainly macrocyclic-derived receptors across quite systematic changes in structure, combined with analysis of multiple crystal structures, allowed us to identify the crucial structural features that are likely required for the occurrence of the phenomenon of selective chloride binding. Examination of a subset of other 'case study' receptors reported in the literature as being particularly chloride-selective served as a confirmation of our hypotheses. As such, our findings are valid for all artificial receptors with exceptional selectivity for chloride, as well as for natural chloride channel proteins (ClC).

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Section: Resultssupporting

confidence: 53%

Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

et al. 2017

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“…The same research group also provided anion receptors based on 7,7 0 -diamido-2,2 0 -diindolylmethane by using the same reaction to prepare 7-amino-3-methylindole. 150,151 This procedure represents a valuable alternative synthesis of 7-amino indole with respect to that proposed by Owa, 111 which starts from already prepared 7-bromoindole, via metallation, azide substitution and finally reduction. In fact, from nitrobenzene to 7-aminoindole, Jurczak's method is a two-step procedure, 148 while Owa's reaction is a four-step one.…”

Section: Miscellaneousmentioning

confidence: 99%

Applications of Bartoli indole synthesis

2014

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In 1989, the reaction of vinyl magnesium halides with ortho-substituted nitroarenes leading to indoles was discovered. This reaction is now frequently reported as the "Bartoli reaction" or the "Bartoli indole synthesis" (BIS). It has rapidly become the shortest and most flexible route to 7-substituted indoles, because the classical indole syntheses generally fail in their preparation. The flexibility of the Bartoli reaction is great as it can be extended to heteroaromatic nitro derivatives and can be run on solid support. This review will focus on the use of the Bartoli indole synthesis as the key step in preparations of complex indoles, which appeared in the literature in the last few years.

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“…There are several types of hydrogen‐bonding building blocks that contain (benzo)pyrrole, urea, and amide units . Owing to their relatively high anion affinity, bisamide building blocks constructed of aromatic skeletons are particularly attractive, as they are readily incorporated into more complex macrocyclic, cryptand, and polycyclic structures ,.…”

Section: Introductionmentioning

confidence: 99%

The Influence of Binding Site Geometry on Anion‐Binding Selectivity: A Case Study of Macrocyclic Receptors Built on the Azulene Skeleton

Lichosyt

Wasiłek

Dydio

et al. 2018

Chemistry A European J

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An understanding of host-guest noncovalent interactions lies at the very heart of supramolecular chemistry. Often a minute change to the structure of a host molecule's binding site can have a dramatic impact on a prospective host-guest binding event, changing the relative selectivity for potential guest molecules. With the overall goal of aiding the rational design of selective and effective receptors for anions, we have studied the influence of small perturbations in binding site geometry for a series of five closely related 20-membered macrocyclic tetra-amide receptors, constructed from two building blocks from a pool of azulene-5,7-bisamide, azulene-1,3-bisamide, and dipicolinic bisamide units. The solid-state structures revealed that the conformational preferences of the free receptors are driven by the inherent preferences of the building blocks, yet in some cases the macrocyclic topology is able to over-ride these to promote pre-organized conformations favorable for anion binding. The solid-state structures of the chloride complexes of these receptors revealed that although all the receptors can adapt to binding to the challenging small Cl guest with all the NH groups, only receptors containing azulene-5,7-bisamide units form short and linear, and therefore strong, hydrogen-bonding interactions. These conclusions are further supported by studies in solution. Although all the receptors showed high affinities toward a series of anions (H PO , PhCO , Cl , and Br ), even in a highly competitive polar medium (DMSO/25 % MeOH), only receptors containing azulene-5,7-bisamide units exhibited non-inherent selectivity for Cl over PhCO , breaking the Hofmeister trend of selectivity. The data presented herein highlight the privileged properties of the azulene-5,7-bisamide building block for binding to chloride anions and provide guidelines for the construction of selective and efficient anion receptors with prospective practical applications.

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Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Cited by 11 publications

References 24 publications

Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

Applications of Bartoli indole synthesis

The Influence of Binding Site Geometry on Anion‐Binding Selectivity: A Case Study of Macrocyclic Receptors Built on the Azulene Skeleton

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