[10]Paracyclophanediamides and their octadehydro derivatives: novel exotopic receptors with hydrogen-bonding sites on the bridge

Katoono, Ryo; Kawai, Hidetoshi; Fujiwara, Kenshu; Suzuki, Takanori

doi:10.1016/j.tetlet.2004.09.115

Cited by 16 publications

(7 citation statements)

References 18 publications

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“…10). Planarchiral compounds are structurally interesting and have potential as frameworks for functional materials such as chiral discriminators [80,81], chiral polymers and supramolecules [82,83], as well as guest receptors [84]. The rotation of the units leads to the exchange of conformers and racemization, so inhibiting the rotational motion is necessary for isolating planar-chiral pillar [5]arenes.…”

Section: Synthesis Of Pillar[6]arenesmentioning

confidence: 99%

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Ogoshi

2011

J Incl Phenom Macrocycl Chem

167

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In 2008, we reported a new class of macrocyclic hosts and named ''Pillar[5]arenes''. They combine the advantages and aspects of traditional hosts and have a composition similar to those of typical calix[n]arenes. Pillar[5]arenes have repeating units connected by methylene bridges at the para-position, and thus they have a unique symmetrical pillar architecture differing from the basket-shaped structure of meta-bridged calix[n]arenes. Pillar[5]arenes show high functionality similar to cyclodextrins, and can capture electron accepting guest molecules within their cavity similarly to cucurbit[n]urils. In this review, the synthesis, structure, rotation, host-guest properties, planar chirality and functionality of pillar[5]arenes are discussed, along with pillar[5]arene-based supramolecular architectures and the challenges in synthesizing pillar[6]arenes.

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Section: Synthesis Of Pillar[6]arenesmentioning

confidence: 99%

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Ogoshi

2011

J Incl Phenom Macrocycl Chem

167

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“…Surprisingly, the hydrolysis of 7 and 8 using a mixture of CAN (10 mol‐%) and 6 n HCl (0.01 mL) was successful, giving good yields of diketones 15 and 16 which were isolated and characterized (Scheme ). The dioxo[4.4]cyclophanes are important targets in host molecule chemistry due to their ability to act as exocyclic receptors (e.g., for nucleic acids)17 or they can be used as building blocks for further transformations. Despite the difficulties involved in the deprotection step, we obtained dioxo[4.4]cyclophanes 15 and 16 in total yields of 41 and 61 %, respectively.…”

Section: Resultsmentioning

confidence: 99%

New [4.4]Cyclophane Diketals, Monoketones, and Diketones: Design, Synthesis, and Structural Analysis

Bogdan¹,

Grosu²,

Condamine³

et al. 2007

Eur J Org Chem

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The synthesis of some new [4.4]cyclophane diketals, monoketones, and diketones in good yields is reported along with the unusually low reactivity towards hydrolysis of the spiro‐1,3‐dioxane rings connected to the cyclophane bridges. The structural analysis carried out by X‐ray diffraction, NMR spectroscopy, and mass spectrometry shows significant intra‐ and intermolecular π–π and C–H–π interactions. The rotation of the aromatic rings and the flipping of the bridges have been investigated by molecular modeling and variable‐temperature NMR experiments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…Planar-chiral compounds are structurally appealing and potentially applicable in various functional materials such as chiral discriminators [1–2], chiral polymers, supramolecular sensors [3] and chiral guest receptors [4–5]. Planar-chiral macrocyclic molecules are particularly interesting in the context of the host–guest complexation properties [6–8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

Fan

Guo

et al. 2019

Beilstein J. Org. Chem.

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Planar chiral pillar[5]arene derivatives (P5A-DPA and P5A-Py) bearing bulky fluorophores were obtained in high yield by click reaction. The photophysical properties of both compounds were investigated in detail. P5A-DPA with two 9,10-diphenylanthracene (DPA) pigments grafted on the pillar[5]arene showed a high fluorescence quantum yield of 89.5%. This is comparable to the monomer DPA-6, while P5A-Py with two perylene (Py) pigments grafted on the pillar[5]arene showed a significantly reduced quantum yield of 46.4% vs 78.2% for the monomer Py-6. The oxygen-through-annulus rotation of the phenolic units was inhibited for both compounds due to the bulky chromophore introduced, and the resolution of the enantiomers was achieved due to the bulky size of the fluorophores. The absolute configuration of the enantiomers was determined by circular dichroism (CD) spectra. The solvent-induced aggregation behavior was investigated with the enantiopure P5A-DPA and P5A-Py. It was found that the CD signals were enhanced by aggregation. P5A-DPA showed aggregation-induced emission enhancement, while P5A-Py showed aggregation-induced emission quenching, accompanied by excimer emission when aggregating in water and THF mixed solution.

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[10]Paracyclophanediamides and their octadehydro derivatives: novel exotopic receptors with hydrogen-bonding sites on the bridge

Cited by 16 publications

References 18 publications

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

New [4.4]Cyclophane Diketals, Monoketones, and Diketones: Design, Synthesis, and Structural Analysis

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

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