Tuning the anion binding properties of calixpyrroles by means of p-nitrophenyl substituents at their meso-positions

Brunò, Giuseppe; Cafeo, Grazia; Kohnke, Franz H.; Nicolò, Francesco

doi:10.1016/j.tet.2007.07.060

Cited by 55 publications

(34 citation statements)

References 45 publications

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“…[3,4] The introductiono ft wo aryl groups in opposed meso-carbons renders the so-called "two-wall" calix [4]pyrrole as two possible constitutionali somers ( Figure 1). [4][5][6][7][8] In cone conformation,t he a,aisomer displays ap olar aromatic cleft ideal for the binding of mono-atomic spherical anions that is, chloride. The anion establishes four simultaneoushydrogenb onds with the pyrrole NHs and it is sandwiched between the opposing meso-aryl substituents, which are oriented in ap arallel arrangement.…”

Section: Introductionmentioning

confidence: 99%

Influence of the Attachment of a Gold(I) Phosphine Moiety at the Upper Rim of a Calix[4]pyrrole on the Binding of Tetraalkylammonium Chloride Salts

Sun

Aragay

Pinto

et al. 2020

Chemistry A European J

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We report the synthesis of an unprecedented mono‐gold(I) phosphine complex based on a “two‐wall” aryl‐ethynyl extended calix[4]pyrrole. We describe and compare the binding properties of the parent 10α,20α‐bis‐aryl‐ethynyl calix[4]pyrrole ligand and the prepared organometallic compound as receptors for tetraalkylammonium chloride salts in dichloromethane and acetone. We describe the results of 1H NMR, UV–Vis titrations and isothermal titration calorimetry (ITC) experiments in dichloromethane and acetone, aiming to thermodynamically characterize the formed complexes. The obtained results indicate a noticeable decrease in the binding affinity of the chloride for the mono‐gold(I) receptor 1 compared to the parent ligand 2. The increase in the negative value of the electrostatic surface potential at the center of the aromatic ring of the gold(I) meso‐aryl‐ethynyl substituent serves to explain the observed results and the presence in solution of the chloride complex of 1 as a mixture of two conformers.

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Section: Introductionmentioning

confidence: 99%

Influence of the Attachment of a Gold(I) Phosphine Moiety at the Upper Rim of a Calix[4]pyrrole on the Binding of Tetraalkylammonium Chloride Salts

Sun

Aragay

Pinto

et al. 2020

Chemistry A European J

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“…Standard HPTS assay Compound 1 [25,26] was selected as representativeo f" two-wall" aryl extended calix [4]pyrrole carriers. Compound 1 bears two p-acidic meso-aromatic substituents, binds chloride with high affinity in acetonitrile solutiona nd showed good anion transport activities.…”

Section: Resultsmentioning

confidence: 99%

Influence of the Insertion Method of Aryl‐Extended Calix[4]pyrroles into Liposomal Membranes on Their Properties as Anion Carriers

Martínez‐Crespo

Sun‐Wang

Ferreira

et al. 2019

Chemistry A European J

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We disclose the results of our investigations on the influence that the insertion method of aryl‐extended calix[4]pyrrole into liposomal membranes exerts on their properties as anion carriers. We use the standard HPTS assay to assess the transport properties of the carriers. We show that the post‐insertion of the carrier, as DMSO solution, assigns better transport activities to the “two‐wall” α,α‐aryl‐extended calix[4]pyrrole 1 compared to the “four‐wall” α,α,α,α‐counterpart 2 . Notably, opposite results were obtained when the carriers were pre‐inserted into the liposomal membranes. We assign this difference to an improved incorporation of carrier 2 into the membrane when delivered by the pre‐insertion method. On the other hand, carrier 1 shows comparable levels of transport independently of the method used for its incorporation. Thus, an accurate comparison of the chloride transport activities featured by these two carriers demands their pre‐incorporation in the liposomal membranes. In contrast, using the lucigenin assay with the pre‐insertion method both carriers displayed similar transport efficiencies.

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“…Researchers have also investigated the ability of calix [4]pyrrole isomers containing internally directed CH hydrogen bond donors [37] to bind anions. In addition, the effects of incorporating nitroaromatic rings into the calix [4]pyrrole backbone to provide additional CH hydrogen bond donors [38] has been studied. Maitra and coworkers [39] developed the cholaphane receptor 6.…”

Section: Interactions In Anion Receptorsmentioning

confidence: 99%

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

McDonald

Hua

Flood

2010

Topics in Heterocyclic Chemistry

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As the field of anion supramolecular chemistry continues to grow in its sophistication and understanding of the noncovalent interactions used to effectively bind anions, there exists new theoretical and experimental evidence for a necessary reexamination of the way in which the field views hydrogen bond donors. The heteroatom based hydrogen-bond donors (e.g., NH and OH) are well-known to provide strong stabilization to negatively charged species. However, new findings point to the untapped stabilization energy that lay dormant in extrinsically-activated CH hydrogen bonds. Computational studies showed that an activated aliphatic or aromatic CH can provide an amount of anion stabilization in the gas phase approaching that of conventional NH based donors. Discovery of the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition to provide 1,2,3-triazoles and the ability to readily "click" this functionality into anion receptors has allowed extensive experimental investigation of the ideas posed by these calculations. This chapter will focus on the evolution of the CH hydrogen bond from being viewed as a weak, secondary interaction to now being utilized as a powerful source of anion stabilization in macrocyclic and oligomeric receptors. In addition, the application of the anion binding power of the 1,2,3-triazole towards the preparation of mechanically interlocked structures will also be discussed.

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Tuning the anion binding properties of calixpyrroles by means of p-nitrophenyl substituents at their meso-positions

Cited by 55 publications

References 45 publications

Influence of the Attachment of a Gold(I) Phosphine Moiety at the Upper Rim of a Calix[4]pyrrole on the Binding of Tetraalkylammonium Chloride Salts

Influence of the Attachment of a Gold(I) Phosphine Moiety at the Upper Rim of a Calix[4]pyrrole on the Binding of Tetraalkylammonium Chloride Salts

Influence of the Insertion Method of Aryl‐Extended Calix[4]pyrroles into Liposomal Membranes on Their Properties as Anion Carriers

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

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