Tetraphenylethene-Embedded Pillar[5]arene and [15]Paracyclophane: Distorted Cavities and Host–Guest Binding Properties

Abstract

Two aggregation-induced emission (AIE) macrocycles (DMP[5]-TPE and PCP[5]-TPE) were prepared by embedding Tetraphenylethene (TPE) unit into the skeletons of Dimethoxypillar[5]arene (DMP[5]) and [15]Paracyclophane ([15]PCP) at meso position, respectively. In crystal, the PCP[5]-TPE showed a distorted cavity, and the incubation of hexane inside the DMP[5]-TPE cavity caused a distinct change in the molecular conformation compared to PCP[5]-TPE. There was no complexation between PCP[5]-TPE and 1,4-dicyanobutane (DCB). UV absorption experiments showed the distorted cavity of DMP[5]-TPE hindered association with DCB.

Tetraphenylethylene-embedded [15]paracyclophanes: AIEgen and macrocycle merged novel supramolecular hosts used for sensing Ni2+ ions

“…Unlike calixarenes, the exploration of meso-functionalization of pillararenes (also a class of [1 n ]PCPs with alkyloxy groups at the para position of the benzene rings 17,18 ) has just started. [19][20][21][22] Following our continuing research interest in constructing functional [1 n ]PCP materials, [23][24][25] we turned our attention to this rarely explored synthetic territory.…”

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

“…Furthermore, Huang’s group reported the preparation of [1 5 ]­paracyclophenone and its fluorenone-containing derivatives by first oxidizing the methylene groups of [1 5 ]­PCP to carbonyl groups . Recently, tetraphenylene was incorporated into [1 5 ]­PCP skeleton at methylene-bridged sites via the McMurry coupling reaction. , However, the functionalization and partial derivatization of [1 n ]­PCP at phenylene sites have been rarely explored, and it remains a challenge to introduce different substituents to the phenyl rings of [1 n ]­PCP. Once this challenge is overcome, the diversity of the [1 n ]­PCP families will be greatly expanded and more properties of them will also be discovered.…”

Host–guest binding selectivity of ethylated pillar[5]arene (EtP5A) towards octane, 1,7-octadiene, and 1,7-octadiyne: a computational investigation

“…During the last two decades, molecular recognition via intermolecular weak interactions, involving hostguest inclusion complex formation with supramolecular macrocyclic compounds, such as cucurbit[n]urils, calix[n]arenes, cyclodextrins, cyclophanes, cyclopeptides, and pillar[n]arenes, has become an interesting new route to construct sophisticated and precisely modelled biological systems with multiple functions [1][2][3][4][5][6]. In particular, pillar [n]arenes which were rst reported in 2008 [7] have attracted considerable attention due to their signi cant importance in biomedical applications, biology, chemistry, physics, material science, nanotechnology, and environmental applications [8][9][10][11][12][13][14][15]. There exists evergrowing interest toward the usage of macrocyclic molecules as hosts to encapsulate drugs, which inherently provides more resistance to the drug degradation [16,17].…”