Deep cavitand vesicles – multicompartmental hosts

Kubitschke, Jens; Javor, Sacha; Rebek, Julius

doi:10.1039/c2cc34065h

Cited by 28 publications

(17 citation statements)

References 35 publications

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“…We began our work using resorcin [4]arene benzimidazole cavitands 1-3, calixarenes 4-6, and pillar[n]arenes 7 and 8, all of which are known to be hosts for various smallmolecule ammonium guests. Our screening partners have a guest-fluorophore conjugate structure (9)(10)(11)(12), where a small-molecule handle is attached to a fluorophore payload ( Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…[9] New hosts have emerged that are capable of self-micelle formation and compartmentalization of payloads. [10] Resorcinarenes have also formed ion channels in lipid environments. [11] This body of work has encouraged us to apply these results to cellular systems; it has been shown that resorcinarene cavitands can promote the endocytosis of fluorescein, so long as a complementary choline handle is attached.…”

Section: Introductionmentioning

confidence: 99%

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Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

2014

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A series of supramolecular calixarenes efficiently transport distinct molecular species through a liquid membrane when attached to a receptor-complementary choline handle. Calix-[6]arene hexacarboxylic acid was highly effective at transporting different target molecules against a pH gradient. Both carboxylic- and phosphonic-acid-functionalized calix[4]arenes effect transport without requiring a pH or ion gradient. NMR binding studies, two-phase solvent extraction, and three-phase transport experiments reveal the necessary and subtle parameters to effect the transport of molecules attached to a choline “handle”. On the other hand, rescorin[4]arene cavitands, which have similar guest recognition profiles, did not transport guest molecules. These developments reveal new approaches towards attempting synthetic-receptor-mediated selective small-molecule transport in vesicular and cellular systems.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

2014

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“…For the NP synthesis, deionised (DI) water was purified by using a Millipore Milli‐Q RG ultrapure water system. Pyridine‐2‐carbohydrazide, [Fe(py) 4 (NCBH 3 ) 2 ], thioctic acid N ‐hydroxysuccinimide (NHS) ester and 2,5,8,11,14‐pentaoxaheptadecan‐17‐oic acid were synthesised according procedures reported in the literature. 1‐Pyrene carboxylic acid NHS ester was prepared by slight modification of a previously reported procedure, with 9:1 CH 2 Cl 2 /ethyl acetate rather than neat CH 2 Cl 2 as the eluting solvent during purification by column chromatography.…”

Section: Methodsmentioning

confidence: 99%

Towards Dual‐Functionality Spin‐Crossover Complexes

et al. 2018

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The multistep synthesis of a versatile new 4‐substituted 3,5‐bis(2‐pyridyl)‐1,2,4‐triazole (Rdpt) ligand, 4‐[4‐(2‐aminomethyl)phenyl]‐3,5‐bis(2‐pyridyl)‐4 H‐1,2,4‐triazole (apdpt), is reported, which features a reactive aminomethyl para‐substituent on the phenyl group that points “out of the back” of the triazole. This enables further functionalisation under mild conditions by using a range of esters to form an amide link. Specifically, this proof of principle study demonstrates the synthesis of apdpt successfully appended with gold‐binding thioctic acid (tpdpt), graphene‐binding/emissive pyrene/propylpyrene (prdpt/pbdpt), and a Langmuir–Blodgett film‐forming polyethylene glycol (PEG) tail (pgdpt). These ligands are subsequently reacted with [Fe(pyridine)4(NCBH3)2] to give the mononuclear iron(II) complexes [Fe(Rdpt)2(NCBH3)2]⋅solvent, in which Rdpt/solvent is tpdpt/2.5 H2O (1), prdpt/0.5 CHCl3⋅H2O (2), and pbdpt/0.5 CHCl3⋅2 H2O (3), as red powders. Magnetic studies on these powders indicate that the complexes undergo only very gradual and incomplete spin crossover, from completely or mostly high spin at 300 K, to half or three‐quarters high spin at 50 K. Gold nanoparticles are successfully functionalised with the thioctic acid tpdpt ligand to give tpdpt@Au with an average diameter (as determined by TEM) of (3.1±0.7) nm. Preliminary studies on the two pyrene systems in dimethylformamide show that upon excitation at λ=345 nm the blue fluorescence observed for the free ligands is retained, essentially unaffected, in the respective complexes.

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“…Resorcin [4]arenes are synthetic organic compounds able to form a hemispherical structure with a diameter of ca. 10 Å at the upper rim and a hydrophobic cavity with an internal volume of 350 Å 3 that can accommodate many organic molecules [10]. These macrocycles are synthesized starting from resorcinol or 1,2,3-trihydroxyphenol and an appropriate aldehyde, which addresses the chemical characteristics of the lower rim [11].…”

Section: Catalysis Into Resorcinarene Hexameric Capsulesmentioning

confidence: 99%

Catalysis inside Supramolecular Capsules: Recent Developments

2019

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In the last decades, supramolecular chemists have developed new molecular receptors able to include a wide range of guests. In addition, they have designed synthetic hosts able to form capsules having an internal volume of thousands of Å3. This inner space shows different features from the bulk solution. In particular, this environment has recently been employed to perform chemical reactions, obtaining reaction products different from the “normal” conditions. These supramolecular capsules act as nanoreactors, catalyzing many chemical transformations. This review collects the recent developments (since 2015) in this field, focusing on supramolecular capsules based on resorcinarene hexameric capsules and metal-cage capsules.

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Deep cavitand vesicles – multicompartmental hosts

Cited by 28 publications

References 35 publications

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

Towards Dual‐Functionality Spin‐Crossover Complexes

Catalysis inside Supramolecular Capsules: Recent Developments

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