Pillarquinones and Pillararenequinones

Cao, Derong; Meier, Herbert

doi:10.1002/ijch.201800007

Cited by 15 publications

(4 citation statements)

References 59 publications

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“…This conclusion was confirmed by detailed computational studies 14 . Other groups have also reported electrochemical data on pillar [5]quinones 15,16 . However, expansion of the oxidized macrocycles to the pillar [6]arene framework has proven synthetically challenging, so there are only a few hostguest reports on a pillar [6]arene compound in which only one of the aromatic units is replaced by a quinone 17,18 .…”

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confidence: 99%

Visualization and quantitation of electronic communication pathways in a series of redox-active pillar[6]arene-based macrocycles

et al. 2020

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While oxidized pillar[5]arenes with 1-5 benzoquinone units are known, very few examples of oxidized pillar[6]arenes have been reported. We describe here the synthesis, characterization and electrochemical behavior of a series of macrocyclic hosts prepared by the stepwise oxidation of 1,4-diethoxypillar[6]arene, resulting in high-yield and high-purity isolation of two constitutional isomers for each macrocycle, in which two, three or four 1,4-diethoxybenzene units are replaced by benzoquinone residues. A careful structural comparison with their counterparts in the pillar[5]arene framework indicates that the geometries of the macrocycles are better described as non-Euclidean hyperbolic hexagons and elliptic pentagons, respectively. A comprehensive computational study to determine anisotropic induced current density (ACID) allows us to visualize and quantify through-space and through-bond communication pathways along the macrocyclic belt. Experimental and simulated voltammetric data, as well as UV-vis spectra, of the new macrocycles afford insights into the various electronic communication pathways in these compounds.

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confidence: 99%

Visualization and quantitation of electronic communication pathways in a series of redox-active pillar[6]arene-based macrocycles

et al. 2020

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“…This led to the rapid discovery of series of macrocycles, including biphenyl[n]arenes, 20 prism[n]arenes, 21 rhombicarene, 22 pagoda[n]arenes, 23 saucer[n]arenes, 24 leggero pillar [5]arenes, 25 octopus [3]arenes, 26 acridane[n]arenes, 27 methylenebridged naphthotubes, 28 and others, 29−31 over the last five years. In addition, the modification at phenylene sites, 32,33 methylene bridge, 34,35 or upper/lower rims 36,37 of P[n]s resulted in pillar[n]arene[m]quinones, 38 tiara[n]arenes, 39 and others. 40−43 The advancement in the modification methods of pillar[n]arenes led to the development of a new strategy to synthesize [1 5 ]paracyclophane (PCP) and [1 6 ]paracyclophane in 2019.…”

Section: ■ Introductionmentioning

confidence: 99%

“…This led to the rapid discovery of series of macrocycles, including biphenyl[ n ]arenes, prism[ n ]arenes, rhombicarene, pagoda[ n ]arenes, saucer[ n ]arenes, leggero pillar[5]arenes, octopus[3]arenes, acridane[ n ]arenes, methylene-bridged naphthotubes, and others, − over the last five years. In addition, the modification at phenylene sites, , methylene bridge, , or upper/lower rims , of P[ n ]s resulted in pillar[ n ]arene[ m ]quinones, tiara[ n ]arenes, and others. − …”

Section: Introductionmentioning

confidence: 99%

Pseudo[n]-pillar[5]arenes: Synthesis, Structures, and Host–Guest Binding Properties

Zhuang

Yusran

et al. 2023

J. Org. Chem.

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[1 n ]Paracyclophane has been known for nearly 40 years, but its derivatives and properties are understudied in comparison to those of other macrocyclic compounds. By the modification of pillar[5]arene, we successfully obtained five electron-rich pentagonal macrocycles (pseudo[n]-pillar[5]arenes, n = 1–4) with the decrease of substituted phenylenes one after another, achieving the partial derivatization of [15]paracyclophane skeleton at its phenylene sites. Pseudo[n]-pillar[5]arenes (P[n]P[5]s) served as a kind of macrocyclic host to form complexes with various guests, such as dinitriles, dihaloalkanes, and imidazolium salt, in a 1:1 host–guest stoichiometric ratio. The binding constants with the guest gradually reduce along the decrease of substituted phenylene segments from host P[1]P[5] to P[4]P[5]. It is worthy to note that P[n]P[5]s can adjust their conformations to the “pillar-like” shape effectively when binding with succinonitrile in the solid state.

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“…Pillar[ n ]arenes − are one of the youngest members of the vast macrocyclic family. Nevertheless, owing to their unique cylindrical shape and electron-rich cavity, as well as adjustable macrocycle’s size, pillar[ n ]arenes have already found application in a number of supramolecular chemistry branches such as sensing, , supramolecular self-assemblies, − stimuli-responsive supramolecular polymers, − and model systems to study various noncovalent interactions. , Moreover, dealkylated pillararenes ,, represent the distinctive class of paracyclophane macrocycles due to the presence of redox-active hydroquinone moieties which enables in situ electrochemical detection of a guest binding as well as altering the electronic properties of the macrocycle via oxidation/reduction (using redox stimulus). − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thiapillar[6]arenes Bearing Redox-Active (Hydro)quinone Groups. Electrochemical and XRD Study

Nikishkin,

Cějka,

Eigner

et al. 2023

J. Org. Chem.

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Pillar[n]arenes are among the newest members of the macrocyclic family. Nevertheless, their conformational behavior and binding properties as well as redox properties of dealkylated pillar[n]arenes are well-studied. At the same time, introducing a heteroatom into a cyclophane macrocycle is already known to alter all the above properties drastically. This study presents a simple synthetic approach based on thia-Michael addition cyclization that readily resulted into hexathiapillar[6]arene with four phenylene units alternated by two redox-active hydroquinone moieties. The straightforward synthesis of the macrocycle enabled a systematic study of its conformation and redox behavior. The modification of hexathiapillar[6]arene afforded five functionalized derivatives, which were studied structurally in detail. The findings revealed interesting redox and structural properties of the macrocycle and its derivatives including the formation of crystal lattices with continuous channels and empty voids.

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Pillarquinones and Pillararenequinones

Cited by 15 publications

References 59 publications

Visualization and quantitation of electronic communication pathways in a series of redox-active pillar[6]arene-based macrocycles

Visualization and quantitation of electronic communication pathways in a series of redox-active pillar[6]arene-based macrocycles

Pseudo[n]-pillar[5]arenes: Synthesis, Structures, and Host–Guest Binding Properties

Synthesis of Thiapillar[6]arenes Bearing Redox-Active (Hydro)quinone Groups. Electrochemical and XRD Study

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