The complexation between ‘Texas sized’ molecular box and linear n-aliphate dianion: en route to supramolecular organic frameworks (SOFs) for selectively CO2 absorption

Ding, Chenjun; Shen, Ming; Xu, Lijin; Gong, Hongmei

doi:10.1016/j.tet.2015.11.062

Cited by 6 publications

(4 citation statements)

References 36 publications

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“…This was attributed to its structure, size, flexibility, and the presence of both cationic imidazolium moieties and neutral aromatic subunits within the ring. Taking these features into account, early on various carboxylate anions were used to explore the host–guest interaction behavior of 1 [ 47 , 48 , 49 ].…”

Section: Host–guest Chemistry Of “Texas-sized” Molecular Boxmentioning

confidence: 99%

“…It was found that most aromatic anions with “widths” less than 5.8 Å thread through the cavity of macrocycle 1 to form pseudorotaxanes. For ease of reference, this was termed the “insert” binding mode ( Figure 1 ) [ 38 , 47 , 48 , 50 ]. Meanwhile, in the case of larger conjugated aromatic anions, it was found that TxSB 1 can serve as “molecular tweezers”, giving rise to sandwich-like complexes.…”

Section: Host–guest Chemistry Of “Texas-sized” Molecular Boxmentioning

confidence: 99%

“…To date, a variety of supramolecular structures have been prepared that exploit the rigid box-like geometry of CBPQT 4+ and the fact that it promotes strong donor-acceptor interactions with various electron-rich species; many of the constructs prepared from CBPQT 4+ have shown potential Table 1. Summary of host-guest binding properties of 1 with a wide range of guests in DMSO-d6 [47,48]. Table 1.…”

Section: Introductionmentioning

confidence: 99%

“…Table 1. Summary of host-guest binding properties of 1 with a wide range of guests in DMSO-d6 [47,48]. Table 1.…”

Section: Introductionmentioning

confidence: 99%

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“Texas-Sized” Molecular Boxes: From Chemistry to Applications

et al. 2021

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The design and synthesis of novel macrocyclic host molecules continues to attract attention because such species play important roles in supramolecular chemistry. However, the discovery of new classes of macrocycles presents a considerable challenge due to the need to embody by design effective molecular recognition features, as well as ideally the development of synthetic routes that permit further functionalization. In 2010, we reported a new class of macrocyclic hosts: a set of tetracationic imidazolium macrocycles, which we termed “Texas-sized” molecular boxes (TxSBs) in homage to Stoddart’s classic “blue box” (CBPQT4+). Compared with the rigid blue box, the first generation TxSB displayed considerably greater conformational flexibility and a relatively large central cavity, making it a good host for a variety of electron-rich guests. In this review, we provide a comprehensive summary of TxSB chemistry, detailing our recent progress in the area of anion-responsive supramolecular self-assembly and applications of the underlying chemistry to water purification, information storage, and controlled drug release. Our objective is to provide not only a review of the fundamental findings, but also to outline future research directions where TxSBs and their constructs may have a role to play.

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Section: Host–guest Chemistry Of “Texas-sized” Molecular Boxmentioning

confidence: 99%

Section: Host–guest Chemistry Of “Texas-sized” Molecular Boxmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Table 1. Summary of host-guest binding properties of 1 with a wide range of guests in DMSO-d6 [47,48]. Table 1.…”

Section: Introductionmentioning

confidence: 99%

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“Texas-Sized” Molecular Boxes: From Chemistry to Applications

et al. 2021

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Selective synthesis and physical properties of a bismacrocycle: Cycloparaphenylene-pillar[5]arene

Zhou¹,

Zhuang

Du³

2024

Chinese Chemical Letters

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Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly

2017

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This feature article summarises recent contributions of the authors in the area of anion-induced supramolecular self-assembly. It is based on the chemistry of a set of tetracationic imidazolium macrocycles, specifically the so-called 'Texas-sized' molecular box, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,4-dimethylenebenzene) (1), and its congeners, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,2-dimethylenebenzene) (2), cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,3-dimethylenebenzene) (3), and cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](2,6-dimethylenepyridine) (4). These systems collectively have been demonstrated as being versatile building blocks that interact with organic carboxylate or sulfonate anions, as well as substrates (e.g., neutral molecules or metal cations). Most work to date has been carried out with 1, a system that has been found to support the construction of a number of stimuli responsive self-assembled ensembles. This macrocycle and others of the 'Texas-sized' box family also show the potential to react as carbene precursors and to undergo post-synthetic modification (PSM) to produce new functional macrocycles, such as trans- and cis-cyclo[2]((Z)-N-(2-((6-(1H-imidazol-1-yl)pyridin-2-yl)amino)vinyl)formamide)[2](1,4-bismethylbenzene) (5 and 6, respectively). On the basis of the work reviewed in this Feature article, we propose that the imidazolium macrocycles 1-4 can be considered as useful tools for the construction of ensembles with environmentally responsive features, including control over self-assembly and an ability to undergo precursor-specific PSM.

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The complexation between ‘Texas sized’ molecular box and linear n-aliphate dianion: en route to supramolecular organic frameworks (SOFs) for selectively CO2 absorption

Cited by 6 publications

References 36 publications

“Texas-Sized” Molecular Boxes: From Chemistry to Applications

“Texas-Sized” Molecular Boxes: From Chemistry to Applications

Selective synthesis and physical properties of a bismacrocycle: Cycloparaphenylene-pillar[5]arene

Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly

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