Abstract:The development of new types of synthetic macrocyclic hosts is always one of the most important and attractive topics in macrocyclic and supramolecular chemistry. Calixarenes, resorcinarenes, cyclotriveratrylenes, pillararenes, and their analogues are all composed of hydroxy-substituted aromatic rings bridged by methylene or methenyl groups and thus can be considered a type of macrocyclic arenes. Because of their unique structural features, easy functionalization, and wide applications in many research areas, … Show more
“…Furthermore, we show that ( R , S p * )‐ H 2 4 and ( R , R p * )‐ H 2 5 have different affinities for chiral viologen guest molecules. (for recent other chiral cage compounds, see refs …”
As part of a project aimed at the development of chiral processive catalysts that can write information on a polymer chain we describe the synthesis of two optically active porphyrin macrocycles, which are prepared in 3 steps from an achiral precursor compound. Fluorescence and
1
H‐NMR studies show that one of the macrocycles displays selectivity in the binding of chiral viologen guest molecules.
“…Furthermore, we show that ( R , S p * )‐ H 2 4 and ( R , R p * )‐ H 2 5 have different affinities for chiral viologen guest molecules. (for recent other chiral cage compounds, see refs …”
As part of a project aimed at the development of chiral processive catalysts that can write information on a polymer chain we describe the synthesis of two optically active porphyrin macrocycles, which are prepared in 3 steps from an achiral precursor compound. Fluorescence and
1
H‐NMR studies show that one of the macrocycles displays selectivity in the binding of chiral viologen guest molecules.
“…Macrocyclic hosts are the major workhorses in supramolecular chemistry. [1] Each macrocycle has its own unique properties and finds applications in quite different fields.M acrocyclic arenes (Scheme 1), [2] including classic calix[n]arenes [3] and more recently emerging pillar[n]arenes, [4] helic-[n]arenes, [5] and biphen[n]arenes, [6] are aq uite unique class of macrocyclic hosts.T hey are readily available by reacting phenols or their derivatives with paraformaldehyde,a nd can be further functionalized and modified according to different demands.C onsequently,m acrocyclic arenes have found diverse applications,s ignificantly enriching the toolbox of supramolecular chemistry.…”
mentioning
confidence: 99%
“…Another feature of these macrocycles is that they are fluorescent and may be used as fluorescent sensors. [11] In view of the successes achieved with phenol-based macrocyclic arenes, [2,3,14] it can be anticipated that there will be ab right future for prism-[n]arenes.…”
Phenol‐based macrocyclic arenes have been widely used in supramolecular chemistry, significantly enriching the toolbox of the field. In contrast, naphthol‐based macrocyclic arenes are rather underdeveloped. Very recently, Gaeta and co‐workers successfully synthesized such macrocycles (referred to as prism[n]arenes) with good guest‐binding ability by reacting 2,6‐dimethoxynaphthalene with paraformaldehyde under optimized conditions. In view of the simple synthesis and good host–guest chemistry, we anticipate that this macrocycle will find similar success and wide applications as the phenol‐based macrocyclic arenes.
“…The 1,8,13-trihalogenatedt riptycenes were then converted to 1,8,13-functionalized triptycenes. Triptycenei sarigid and symmetric propeller shaped organic molecule with ab icyclo [2.2.2]octatriene skeleton. [1] Because of these special properties,t riptycenes have been used as basic units of host molecules in the field of molecularr ecognition, [2] supramolecular chemistry, [3] macromolecules, [4] materials ciences, [5] and metal ligands. [6] However, functionalized triptycenes are not easily obtained because major synthetic methodsf or triptycenes are limited to cycloaddition of benzyne [7] or benzoquinone [8] to anthracenes.…”
1,8,13‐Trialkyl(aryl)silyl‐9‐hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3‐silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step‐by‐step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13‐trihalogenated triptycenes were then converted to 1,8,13‐functionalized triptycenes.
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