Pagoda[5]arene with Large and Rigid Cavity for the Formation of 1∶2 Host–Guest Complexes and Acid/Base-Responsive Crystalline Vapochromic Properties

Han, Xiao-Ni; Zong, Qian‐Shou; Han, Ying; Chen, Chuan‐Feng

doi:10.31635/ccschem.021.202100870

Cited by 76 publications

(37 citation statements)

References 55 publications

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“…Among them, macrocyclic arenes incorporating aromatic units in the walls of their cavities have attracted particular attention since these units endow the macrocycles not only with appealing molecular recognition features but also with potential optical and electronic properties. More recently, a number of new macrocyclic hosts, including corona[ n ]arenes, naphthotubes, biphen[ n ]arenes, tiara[5]arene, prism[ n ]arenes, pagoda[ n ]arenes, saucer[ n ]arenes, and many others with host–guest properties, have appeared on the scene. Clearly, the development of new kinds of hosts with well-defined structures and properties has been one of the most popular research topics in recent years, as well as also being an indispensable source and foundation of innovation in the field of host–guest chemistry …”

Section: Introductionmentioning

confidence: 99%

Corralarenes: A Family of Conjugated Tubular Hosts

Han

Wang

et al. 2022

J. Am. Chem. Soc.

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Despite the advances in host−guest chemistry, macrocyclic hosts with deep cavities are far from abundant among the large number of wholly synthetic hosts described in the literature. Herein, we describe the design and synthesis of two new tubular hosts, namely, corral[4]arene and corral[5]arene. The former has been isolated and characterized as two conformational diastereoisomers, one is centrosymmetric and the other asymmetric. The latter, a fivefold symmetrical and flexible host, has also been investigated in detail. It is composed of five 4,4′-dimethoxybiphenyl units bridged by ethynylene linkers at their 2,2′-positions and adopts a pentagonal conformation with a tubular-shaped cavity in the presence of guests. This structure endows corral[5]arene not only with a conjugated backbone, capable of bright fluorescent emission (quantum yield, 56%), but also a deep π-electron-rich aromatic cavity with remarkable conformational flexibility. The adaptive cavity of corral [5]arene allows it to accommodate a wide range of neutral and positively charged electron-deficient guests with different molecular sizes and shapes. Binding constants between this host and these guests in three different nonpolar organic solvents lie in the range of 10 3 to 10 7 M −1 . Moreover, corral[5]arene exhibits dynamic chirality on account of the axes of chirality associated with each of the five biphenyl units and displays first-order transformation as exhibited by circular dichroism in response to the addition of chiral guests. All these stereochemical features render corral[5]arene an attractive host for a variety of supramolecular and nanotechnological applications.

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Section: Introductionmentioning

confidence: 99%

Corralarenes: A Family of Conjugated Tubular Hosts

Han

Wang

et al. 2022

J. Am. Chem. Soc.

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“…Naturally, it was attempted to broaden this specific subclass of macrocycles by replacing the benzene-based building blocks with larger ones, for instance, naphthalene-derived ones. Unfortunately, all attempts have failed to deliver size-extended bowl-shaped resorcinarene-like macrocycles as of yet. − During the past decade, many new large phenol-based macrocycles, including 3 – 8 (Figure b), − have been reported. − Importantly, in contrast to 1 and 2 , they do not feature R residues at the linking methylene units that conformationally restrict the crown conformation, and increase the solubility of the free phenol derivatives. The higher conformational freedom of the CH 2 -linked macrocycles is revealed in the 1 H NMR spectra.…”

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confidence: 99%

Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly

Pfeuffer-Rooschüz

Schmid

Prescimone

et al. 2021

JACS Au

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A new class of macrocycles denoted as “xanthene[n]arenes” was synthesized. In contrast to most other macrocycles, they feature a conformationally restricted bowl shape due to the attached alkyl groups at the linking methylene units. This facilitates the synthesis of cavitands and the self-assembly to molecular capsules via noncovalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]arene scaffold. Besides a deep cavitand and an oxygen-embedded zigzag hydrocarbon belt[12]arene, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule, demonstrating the potential of xanthene[n]arenes as a new set of macrocyclic building blocks.

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“…As one kind of important soft material, supramolecular gels have drawn much attention during the past two decades due to their intriguing capabilities of stimuli-responsiveness, self-healing, and shape memory. − With the rapid development of macrocyclic chemistry, supramolecular gels based on host–guest motifs emerged as an excellent choice for designing and constructing functional soft materials with versatile topological morphologies and intriguing dynamic properties. − Consequently, various macrocyclic hosts including crown ethers, − calixarenes, , cucurbiturils, , pillararenes, and cyclodextrins , have been exploited extensively to construct supramolecular gels for the applications in self-healing and adhesive materials, − optical materials, − biomaterials, − separation materials, − and molecular machines. , Recently, the macrocycle-based supramolecular gels with chiroptical properties ,− have also been reported; however, such examples are still limited probably due to the insufficiency of the synthetic macrocyclic hosts with stable chiral structures.…”

Section: Introductionmentioning

confidence: 99%

Chiral Bishelic[6]arene-Based Supramolecular Gels with Circularly Polarized Luminescence Property

Guo

Han

et al. 2022

ACS Appl. Polym. Mater.

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In this work, a pair of enantiomeric bishelic[6]arenes (P / M-BH6) was synthesized and utilized to construct chiral supramolecular polymers with achiral luminescent guests through the host–guest interactions. The resulting linear supramolecular polymers could further self-assemble into supramolecular gels with enhanced emission. Moreover, the supramolecular gels with chiral and fluorescence properties exhibited circularly polarized luminescence (CPL) property induced by the chirality transfer from the chiral macrocyclic arene to the achiral guests. Furthermore, a kind of chiral supramolecular gel with white-light emission was conveniently obtained by regulating the ratio of the two achiral guests. This work provides a promising strategy to construct CPL-active supramolecular gels based on the chiral macrocyclic host–guest interactions.

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Pagoda[5]arene with Large and Rigid Cavity for the Formation of 1∶2 Host–Guest Complexes and Acid/Base-Responsive Crystalline Vapochromic Properties

Cited by 76 publications

References 55 publications

Corralarenes: A Family of Conjugated Tubular Hosts

Corralarenes: A Family of Conjugated Tubular Hosts

Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly

Chiral Bishelic[6]arene-Based Supramolecular Gels with Circularly Polarized Luminescence Property

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