Vesicles Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives for Enantioselective Recognition of Organic Anions

He, Qing; Tuo, De‐Hui; Ao, Yu‐Fei; Wang, Qi‐Qiang; Wang, De‐Xian

doi:10.1021/acsami.7b18723

Cited by 14 publications

(9 citation statements)

References 31 publications

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“…It is most likely the variation of the surface zeta (ζ) potential of the anion−π complexation that leads to the enlargement of vesicles. The vesicle–anion interaction has then been extended in chiral recognition . The l -prolinol-substituted amphiphiles 51 undergo aggregation to afford vesicles with a chiral surface.…”

Section: Construction Of Functional Assemblies Based On Anion–π Inter...mentioning

confidence: 99%

Exploring Anion−π Interactions and Their Applications in Supramolecular Chemistry

Wang

2020

Acc. Chem. Res.

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140

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Metrics & MoreArticle Recommendations CONSPECTUS: Noncovalent bond interactions provide primary driving forces for supramolecular processes ranging from molecular recognition to self-assembly of sophisticated abiotic and biological machineries. While hydrogen bonding and π−π interactions are arguably textbook concepts playing indispensable parts in various scientific disciplines, noncovalent anion−π interactions have been emerging as attractive forces between π systems and negatively charged species for just about two decades. At the beginning of this century, three research groups reported independently their computational studies on the interactions between anions and aromatic compounds, proposing attractive anion−π interactions. Since π systems such as aromatic rings are traditionally noted as electron rich entities, anions and π systems would be repulsive to each other if there are any interactions. In stark contrast to the acknowledged cation−π interactions, the seemingly counterintuitive noncovalent anion−π bindings invoked great interest in the following years. Although a plethora of calculations had been published, the lack of experimental evidence cast doubt on the existence of anion−π interactions between anions and charge-neutral aromatic systems.During the same time when anion−π interactions were coined, we were studying the chemistry of novel macrocyclic compounds, namely, heteracalixaromatics, and their applications in supramolecular chemistry. It has been shown that heteracalixaromatics are powerful and versatile macrocyclic hosts to bind various guest species forming interesting assembled structures and organometallic complexes. Being a member of heteracalixaromatics, tetraoxacalix[2]arene[2]triaizne adopts a 1,3-alternate conformational structure yielding a V-shaped cavity or cleft formed by two electron-deficient triazine rings. Advantageously, the macrocycle is able to self-tune the cavity sizes by altering the degrees of conjugation between the bridging oxygen atoms with their bonded aromatic rings in response to the guest species in present, rendering it an ideal tool to explore anion−π interactions. We initiated our study on anion−π interactions using tetraoxacalix[2]arene[2]triazine as a molecular tool with the primary aim to clarify experimentally the uncertainty of whether exclusive anion−π interactions exist between anions and charge-neutral aromatic rings. We provided for the first time concrete evidence substantiating the formation of typical anion−π interaction between the anions and 1,3,5-triazine ring and demonstrated subsequently the generality and binding motifs of anion−π interactions. We have then extended our study to anion−π interaction-directed or -driven anion recognition and selective sensing, transmembrane anion transport, molecular selfassembly, and stimuli-responsive aggregation systems. A number of new generation macrocycles and cages constructed from electron-deficient tetrazine and benzenetriimide segments have also been developed in the meantime, advancing the study ...

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Section: Construction Of Functional Assemblies Based On Anion–π Inter...mentioning

confidence: 99%

Exploring Anion−π Interactions and Their Applications in Supramolecular Chemistry

Wang

2020

Acc. Chem. Res.

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140

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“…1 Actually, in a wider perspective, smart chiral receptor systems also find applications in anion recognition, 2 electroanalysis, 3 and modern technologies like spin filters to improve the efficiency of LED/OLED. 4 So far, chiral sensing structures have been based on a variety of components, such as vesicles, 5 nanostructures, 6 polymers, 7 and ligands with specific moieties or geometries. Among these, polydentate and, more specifically, tripodal ligands proved to be particularly efficient, since they are modular and give robust complexes with high thermodynamic stability.…”

Section: Introductionmentioning

confidence: 99%

Extending substrate sensing capabilities of zinc tris(2‐pyridylmethyl)amine‐based stereodynamic probe

et al. 2019

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Tripodal metal complexes have been widely used for catalysis and more recently also for molecular recognition applications. Their ability in recognition and signal amplification of chiral substrates is because of the setup of the ligand around the metal in a propeller shape. Within this subject, we have recently reported tris(2-pyridylmethyl)amine-and triphenolamine-based complexes for the determination of the enantiomeric excess of various substrates.Herein, we show the versatility of the zinc tris(2-pyridylmethyl)amine-based stereodynamic probe by performing a detailed study of the imine formation process, by the extension of the sensing capabilities to other chiral compounds. A principal component analysis study of the system together with TD-DFT studies highlights the molecular origin of the observed chiroptical properties.

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“…The sophisticated design of ingenious macrocyclic molecules has ever been one of the key driving forces to advance supramolecular chemistry and related fields. Importantly, macrocyclic molecules provide ideal models not only to study the nature of noncovalent interactions but also to obtain a deep understanding of living systems. − Recent years have witnessed tremendous development of a new generation of macrocyclic host molecules named heteracalixaromatics. − Replacement of methylene groups with heteroatoms as the bridging moieties, and the incorporation of various (hetero)aromatics including triazine, pyrimidine, pyrazine, pyridine, and naphthyridine have endowed heteracalixaromatics unique structures and powerful recognition properties. ,,− Oxacalixaromatics, for example, are a typical member of the heteracalixaromatic family and have been remarkably applied in the studies of molecular recognition, − self-assembly, − and stimuli responsive materials . On the other hand, owing to the appealing chemical and structural features such as the strong coordination ability and the outstanding photochemical and photophysical properties, 1,10-phenanthrolines have found extensive applications in organic synthesis, material science, biological systems, and supramolecular chemistry. − To the best of our knowledge, however, heteracalixaromatics that are composed of the 1,10-phenanthroline unit remain unknown.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, Property, and Dinuclear Cu(II) Complexation of Tetraoxacalix[2]arene[2]phenanthrolines

Wang

et al. 2018

Inorg. Chem.

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A number of novel tetraoxacalix[2]arene[2]phenanthrolines 7–11 containing phenanthroline and diverse aromatic linkages were conveniently synthesized by a one-pot protocol between a series of dihydroxy arenes and 1,10-phenanthroline derivatives. Single-crystal diffraction analysis revealed that the resulting macrocycles possess diverse conformational and cavity structures which are regulated by the different aromatic linkages. In line with the length of the aromatic linkages, the distance between the two phenanthroline moieties (d N–N) gradually increases from 6.92 to 13.30 Å, respectively. The physicochemical properties of these macrocyclic compounds were investigated by spectroscopic, CV, and DPV measurements. Owing to the coordination ability of the phenanthroline moieties and the tunable conformational structure, the macrocyclic hosts can form distinct dinuclear complexation with Cu2+. Typically, with a short aromatic linkage the 7b–2Cu(II) complex gives an O-bridged dicopper structure, while with long linkage the 11b–2Cu(II) complex possesses two discrete copper centers. The spectroscopic structure and the redox property of the dicopper complexes were investigated by XPS, CV, and DPV techniques. This work hence provides a platform to access biomimetic copper-containing small-molecule models with well-defined structures.

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Vesicles Constructed with Chiral Amphiphilic Oxacalix[2]arene[2]triazine Derivatives for Enantioselective Recognition of Organic Anions

Cited by 14 publications

References 31 publications

Exploring Anion−π Interactions and Their Applications in Supramolecular Chemistry

Exploring Anion−π Interactions and Their Applications in Supramolecular Chemistry

Extending substrate sensing capabilities of zinc tris(2‐pyridylmethyl)amine‐based stereodynamic probe

Synthesis, Structure, Property, and Dinuclear Cu(II) Complexation of Tetraoxacalix[2]arene[2]phenanthrolines

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