A novel calixsalen macrocycle: metal sensing behavior for Zn2+ and intracellular imaging application

Fu, Yong; Xing, Zhi-Tao; Zhu, Chengcheng; Yang, Hongwei; He, Weijiang; Zhu, Chengjian; Cheng, Yixiang

doi:10.1016/j.tetlet.2011.12.005

Cited by 33 publications

(13 citation statements)

References 35 publications

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“…This arrangement of nitrogen atoms is related to the s‐trans arrangement of the imine bonds connected to a given aromatic ring, in agreement with the 1 H NMR spectra. A similar conformation of imine bonds was observed in the free macrocycles H 3 1 20, 21 and H 3 3 22. The overall shape of the trinuclear complex [Zn 3 4 2 ] is similar to that of the previously reported crystal forms of [Zn 3 1 2 ] grown from methanol or chloroform,8 as well as the new crystal forms of [Zn 3 1 2 ] grown from toluene or the ethanol/dichloromethane mixture reported herein (Figure 3).…”

Section: Resultssupporting

confidence: 73%

“…The molecular structure of the [3+ +3] macrocycle H 3 1, [20,21] which bears tert-butyl substituents, is similar to that of the [3+ +3] Schiff base H 3 3 [22] with methyl substituents.T herea re, however, strikingd ifferences in the packing arrangements of the H 3 1 macrocycle crystallized from acetonitrile [20,21] and the H 3 3 macrocycle crystallized form DMF. [22] Although the latter forms pairs in which one macrocycle acts as ah ostf or the aromatic fragment of the other macrocycle, the former macrocycle forms pairs held together by hydrogen bonds.T he hydrogen-bonded dimers of H 3 1 form ac avity,t he shape and size of which are almosti denticalt ot hose formed by the two macrocyclic units in the [Zn 3 1 2 ]t rinuclearc omplex( Figure 4).…”

Section: Resultsmentioning

confidence: 99%

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Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

Janczak

Prochowicz

Lewiński

et al. 2015

Chemistry A European J

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Three zinc(II) ions in combination with two units of enantiopure [3+3] triphenolic Schiff-base macrocycles 1, 2, 3, or 4 form cage-like chiral complexes. The formation of these complexes is accompanied by the enantioselective self-recognition of chiral macrocyclic units. The X-ray crystal structures of these trinuclear complexes show hollow metal-organic molecules. In some crystal forms, these barrel-shaped complexes are arranged in a window-to-window fashion, which results in the formation of 1D channels and a combination of both intrinsic and extrinsic porosity. The microporous nature of the [Zn3 12 ] complex is reflected in its N2 , Ar, H2 , and CO2 adsorption properties. The N2 and Ar adsorption isotherms show pressure-gating behavior, which is without precedent for any noncovalent porous material. A comparison of the structures of the [Zn3 12 ] and [Zn3 32 ] complexes with that of the free macrocycle H3 1 reveals a striking structural similarity. In H3 1, two macrocyclic units are stitched together by hydrogen bonds to form a cage very similar to that formed by two macrocyclic units stitched together by Zn(II) ions. This structural similarity is manifested also by the gas adsorption properties of the free H3 1 macrocycle. Recrystallization of [Zn3 12 ] in the presence of racemic 2-butanol resulted in the enantioselective binding of (S)-2-butanol inside the cage through the coordination to one of the Zn(II) ions.

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Section: Resultssupporting

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

Janczak

Prochowicz

Lewiński

et al. 2015

Chemistry A European J

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“…6-Formyl-2-(hydroxymethyl)-4-tertbutylphenol was prepared following the previously reported procedure. [26]…”

Section: Methodsmentioning

confidence: 99%

A pentanuclear Er (III) coordination cluster as a catalyst for selective synthesis of 1,2‐disubstituted benzimidazoles

Sarkar

Jana

Nayek

2021

Applied Organom Chemis

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A new tridentate ligand (H 3 L) was prepared from the reaction of 6-formyl-2-(hydroxymethyl)-4-tert-butylphenol and 2-amino-4-nitrophenol. The ligand H 3 L and acetylacetone were treated with Er (NO 3 ) 3 Á5H 2 O, which resulted in the formation of a pentanuclear coordination cluster [Er 5 (LH) 4 (acac) 4 (μ 3 -O) (μ 3 -OH)(H 2 O) 2 ] . 5H 2 O (1) (acac = acetylacetonate). Five Er (III) ions are arranged in a nonlinear fashion in 1. Complex 1 was utilized as a catalyst towards the selective synthesis of 1,2-disubstituted benzimidazole derivativesinvolving o-phenylenediamine and different aldehydes. Yields of 1,2-disubstituted benzimidazole derivatives were in the range of 66%-91%. This study demonstrates the first-ever approach to employ a homo-and pentanuclear lanthanide coordination cluster for catalyzing the synthesis of 1,2-disubstituted benzimidazoles.

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“…Solvents were purchased from Rankem, India. 4‐ tert ‐butyl‐2,6‐diformylphenol was prepared following the previously reported method …”

Section: Methodsmentioning

confidence: 99%

“…4-tert-butyl-2,6-diformylphenol was prepared following the previously reported method. [49] Scheme 4. Friedel-Crafts alkylation reaction of indole and benzaldehyde catalyzed by 1.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

Trinuclear Lanthanide Coordination Clusters: Single‐Molecule‐Magnet Behavior and Catalytic Activity in the Friedel‐Crafts Alkylation Reaction

et al. 2019

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A new multidentate ligand (H3L) was synthesized by the condensation reaction of 4‐tert‐butyl‐2,6‐diformylphenol and 2‐amino‐4‐nitrophenol. The reaction of the ligand with hydrated lanthanide nitrate produced two isostructural trinuclear coordination clusters: [DyLn3L3(DMF)3(H2O)2] ⋅ 3.8DMFLn=Dy (1) and Nd (2) (DMF=N, N‐dimethylformamide). Single‐crystal X‐ray diffraction analysis revealed that there are three lanthanide ions arranged in an almost perfect linear fashion in both complexes. Magnetic studies show single‐molecule‐magnet (SMM) behavior in the Dy derivative with τ0=1.7×10−6 s and a thermal energy barrier of 7.0 cm−1. Both complexes were used as catalysts towards the Friedel‐Crafts alkylation reaction of indole with different aldehydes with yields varying from 59–98 %. Complex 1 showed better catalytic efficiency than complex 2. This is the first report of using trinuclear lanthanide coordination clusters as catalysts for the Friedel‐Crafts alkylation reaction.

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A novel calixsalen macrocycle: metal sensing behavior for Zn2+ and intracellular imaging application

Cited by 33 publications

References 35 publications

Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

A pentanuclear Er (III) coordination cluster as a catalyst for selective synthesis of 1,2‐disubstituted benzimidazoles

Trinuclear Lanthanide Coordination Clusters: Single‐Molecule‐Magnet Behavior and Catalytic Activity in the Friedel‐Crafts Alkylation Reaction

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A novel calixsalen macrocycle: metal sensing behavior for Zn2+ and intracellular imaging application

Cited by 33 publications

References 35 publications

Trinuclear Cage‐Like ZnII Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

Trinuclear Cage‐Like ZnII Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

A pentanuclear Er (III) coordination cluster as a catalyst for selective synthesis of 1,2‐disubstituted benzimidazoles

Trinuclear Lanthanide Coordination Clusters: Single‐Molecule‐Magnet Behavior and Catalytic Activity in the Friedel‐Crafts Alkylation Reaction

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Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties

Trinuclear Cage‐Like Zn^II Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties