Pagoda[4]arene andi-Pagoda[4]arene

Abstract

A new type of macrocyclic arenes, named pagoda[4]arene (P4) and i-pagoda [4]arene (i-P4), were conveniently synthesized by the TFA-catalyzed one-pot condensation of 2,6-dimethoxylanthracene and paraformaldehyde in dichloromethane at room temperature. P4 and i-P4 showed unique square pagoda structures and fixed conformations in solution and also exhibited strong blue fluorescence. Moreover, P4 and i-P4 with deep and rich-electron cavities could not only encapsulate n-hexane and one or two dichloromethane molecules in the solid state but also showed strong binding abilities toward neutral dinitriles with different chain lengths and various nitrogen-containing heterocyclic salts to form 1:1 stable host−guest complexes in both solution and the solid state. In particular, it was also found that with the increase in the alkyl chain length of the dinitriles, the association constants for their complexes with both P4 and i-P4 were markedly increased from glutaronitrile to octanedinitrile as a result of the deep cavities of the macrocycles and multiple intermolecular interactions. Since P4 and i-P4 had stable planar chirality, their efficient resolutions were further achieved by HPLC with a chiral column. Interestingly, the two enantiomers showed mirror-imaged CD signals and excellent CPL properties, which could allow them to have potential applications in chiral luminescent materials.

An intramolecularly self-templated synthesis of macrocycles: self-filling effects on the formation of prismarenes

“…Thus, oxatubarenes, naphthotubes, and naphthocages were reported by Jiang and coworkers that show interesting conformational properties and recognition abilities. [10][11][12][13][14][15][16] The scientific interest toward the design of new macrocyclic hosts 17 with deep cavities and conformational adaptive behavior, 16 has recently prompted us to synthesize new examples of naphthol-based macrocycles named calix [2]naphth [2]arene 18 and prismarenes (Figure 1). 19,20 The first report on prismarenes was mainly focused on the synthesis and recognition properties of pentameric PrS[5] Me macrocycle (Figure 1) constituted by 1,5-methylene bridged 2,6-dimethoxynaphthalene units.…”

Complexation of an Antimicrobial Peptide by Large‐Sized Macrocycles for Decreasing Hemolysis and Improving Stability

“…Design and synthesis of macrocyclic containers with distinctive topological structures and tailored complexation abilities plays a crucial role in supramolecular chemistry during past five decades [1–8] . These macrocycles have made significant progress in different scientific areas, such as host–guest recognition, [9, 10] molecular machinery, [11, 12] supramolecular assembly, [13, 14] smart materials [15, 16] and others [17–21] .…”

<italic>Meso</italic> position functionalized calix[<italic>n</italic>]arenes and pillar[<italic>n</italic>]arenes and their applications

“…[n]芳烃, 以及陈传峰等 [69] 合成的新的蒽环化合物也 具有桥梁亚甲基结构, 类似的化合物还有杯吡啶、杯 吡咯和环三苯, 也都是可以进行自组装的含桥大环芳 烃, 并且分别在药物运载及氨基酸识别 [70,71] 、光学传 感和荧光体系构建有重要应用…”