Macrocyclic and Acyclic Molecules Synthesized from Dipyrrolylmethanes: Receptors for Anions

Mani, Ganesan; Guchhait, Tapas; Kumar, Rajnish; Kumar, Sandeep

doi:10.1021/ol101598e

Cited by 32 publications

(38 citation statements)

References 55 publications

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“…Solvents were purchased from commercial sources and distilled before use by following standard procedures. Diethyldipyrrolylmethane, 41 1,1′-dipyrrolylcyclohexane, 23f and 1,9-bis-(N,N-dimethylaminomethyl)dipyrrolylmethanes, 42 were prepared according to the literature procedures. Pyrrole, dimethylamine hydrochloride, 3-pentanone, and 3,5-dimethylpyrazole were purchased from Aldrich and were used without further purification except pyrrole, which was distilled, and amine hydrochloride, which was dried under vacuum using warm water.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and structural characterization of silver(i), copper(i) coordination polymers and a helicate palladium(ii) complex of dipyrrolylmethane-based dipyrazole ligands: the effect of meso substituents on structural formation

et al. 2015

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A new class of multidentate dipyrrolylmethane based ditopic tecton, 1,9-bis(3,5-dimethylpyrazolylmethyl)dipyrrolylmethane, containing diethyl (L1) or cyclohexylidene (L2) substituents at the meso carbon atom were readily synthesized in 28-45% yields in two different ways starting from dipyrrolylmethanes. A one dimensional coordination polymer structure ([(L2)Ag][BF4])n was obtained when L2 was treated with AgBF4, whereas the analogous reaction between L1 and AgBF4 afforded the dicationic binuclear metallacycle complex [(L1)2Ag2][BF4]2. In addition, yet another coordination polymeric structure [(L1)CuI]n was obtained from the reaction between L1 and CuI. The analogous reaction of L1 with [Pd(PhCN)2Cl2] afforded the binuclear palladium complex [(L1)2Pd2Cl4] having a double-stranded helicate structure. The observed structural differences are attributed to the effects of the substituents present at the meso carbon atom of the ligand, in addition to the nature of the metal centre, coordination number and the preferred geometry.

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Section: Methodsmentioning

confidence: 99%

Synthesis and structural characterization of silver(i), copper(i) coordination polymers and a helicate palladium(ii) complex of dipyrrolylmethane-based dipyrazole ligands: the effect of meso substituents on structural formation

et al. 2015

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“…1). 18 By Schiff base condensation reactions, Mani and co-workers have further prepared a series of large size polyaza macrocycles containing N,N-di(pyrrolylmethyl)-N-methylamine Fig. 17 Then they have designed and synthesized macrocycles L 3 (Fig.…”

Section: Recognition Of Polyaza Macrocyclesmentioning

confidence: 99%

“…15a), and its cavity has a specific size suitable for the recognition of fluoride ion (Fig. X-ray diffraction analysis has showed that the F − anion locate in the cavity center of L 18 to form an inclusion complex, while Cl − and Br − anions situate in the clefts of L 18 to generate chloride/broride complexes (Fig. 43 Then they prepared another hexapyrrolic polyaza cryptand of L 17 with long spacers and larger cavity (Fig.…”

Section: Polyaza Cryptands With Aromatic or Heterocyclic Spacersmentioning

confidence: 99%

Molecular recognition and activation by polyaza macrocyclic compounds based on host–guest interactions

Zhong

2016

Chem. Commun.

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The design and syntheses of supramolecular hosts for the recognition and activation of molecules and anions are one of the most active research fields in supramolecular chemistry, in which polyaza macrocyclic ligands and their complexes have drawn particular attention due to their strong host-guest interactions. This review mainly focuses on the recent progress in the recognition of molecules and anions by polyaza macrocyclic compounds including polyaza macrocycles, polyaza macrobicycles and polyaza macrotricycles, as well as the activation of molecules by polyaza macrocyclic ligands and their metal complexes.

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“…mp >200 °C. 1 (20 mL) was added solid ammonium hydrogen difluoride (0.010 g, 0.18 mmol). The solution was stirred for 10-15 min at room temperature and then allowed to stand for the slow evaporation of solvent to give colorless crystals of 2h formed over a period of three days.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and structural characterization of anion complexes with azacalix[2]dipyrrolylmethane: effect of anion charge on the conformation of the macrocycle

2016

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Tetrahomodiazacalix[2]dipyrrolylmethane 1, [-CH2(C4H3N)CR2(C4H3N)CH2N(Me)-]2 an expanded version of the calix[4]pyrrole system, has the tendency to change its ring conformation (1,3-alternate) upon anion binding analogous to calix[4]pyrrole. However, owing to its tertiary amine nitrogen atoms in the ring, it can be protonated and becomes a powerful cationic receptor for anions, besides its inherent hydrogen bonding features. Macrocycle 1 binds with a series of monoanions BF4(-), Cl(-), PhCOO(-) and ClO4(-), and their X-ray structures showed that the ring conformation constitutes the 1,2-alternate form. Upon binding with dianions SO4(2-), CrO4(2-), SiF6(2-) and S2O3(2-), the ring conformation changes to the cone conformation. The intermediate partial cone conformation results for complexes with NO3(-) and Cr2O7(2-) ions. The change in the orientation of the pyrrole NH groups depending on the charge of the anion demonstrates the flexibility of the macrocycle and the dicationic macrocycle stabilizes the anions via both hydrogen bonding and electrostatic interactions.

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Macrocyclic and Acyclic Molecules Synthesized from Dipyrrolylmethanes: Receptors for Anions

Abstract: A new class of macrocyclic and acyclic molecules was synthesized by the Mannich reactions of dipyrrolylmethanes to investigate anion recognition. The X-ray structures of the macrocycle and sulfate complexes are reported.

Cited by 32 publications

References 55 publications

Synthesis and structural characterization of silver(i), copper(i) coordination polymers and a helicate palladium(ii) complex of dipyrrolylmethane-based dipyrazole ligands: the effect of meso substituents on structural formation

Synthesis and structural characterization of silver(i), copper(i) coordination polymers and a helicate palladium(ii) complex of dipyrrolylmethane-based dipyrazole ligands: the effect of meso substituents on structural formation

Molecular recognition and activation by polyaza macrocyclic compounds based on host–guest interactions

Synthesis and structural characterization of anion complexes with azacalix[2]dipyrrolylmethane: effect of anion charge on the conformation of the macrocycle

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