Conformationally adaptive macrocycles with flipping aromatic sidewalls

Wang, Xiaoping; Jia, Fei; Yang, Liu‐Pan; Zhou, Hang; Jiang, Wei

doi:10.1039/d0cs00341g

Cited by 78 publications

(53 citation statements)

References 48 publications

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“…Macrocyclic pillar[ n ]arene exhibits dynamically racemic planar conformational chirality in solution, whose p R and p S enantiomers are interconvertible by rotation of the repeating hydroquinone unit [18–20] . When a chiral guest enters the cavity of pillar[ n ]arene, one of two chiral p R and p S conformations of pillar[ n ]arene will be induced and becomes excess; this is different from traditional chiroptical sensors using their stable molecular chirality to detect a target analyte [21, 22] .…”

Section: Methodsmentioning

confidence: 99%

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Chen

Sun

et al. 2021

Chemistry A European J

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Chiral α‐amino acids play critical roles in the metabolic process in nearly all life forms. So far, chiral recognition of α‐amino acids has mainly focused on the determination of l/d enantiomers. Herein, selection of planar chiral conformations between water‐soluble pillar[5]arene WP5 and pillar[6]arene WP6 was observed due to α‐side chain or ethyl ester moieties of l‐α‐amino acid ethyl ester hydrochlorides binding with WP5 and WP6, respectively. Therefore, α‐side chain and ethyl ester moieties of l‐α‐amino acid ethyl ester hydrochlorides were recognized by observing the induced CD signal and its inversion. This is a rare example of being able to detect the chiral region around α‐carbon of a chiral α‐amino acid molecule.

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Section: Methodsmentioning

confidence: 99%

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Chen

Sun

et al. 2021

Chemistry A European J

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“…Theoretically, there are two representative conformations for MeBP3, due to flipping of the biphenyl sidewalls ( Figure 1a, MeBP3-I and MeBP3-II). For MeBP3-I, three biphenyl units are arranged in the same orientation, and flipping of one biphenyl panel of MeBP3-I can produce MeBP3-II [55]. Conformer MeBP3-I has D 3 symmetry and thus should give rise to two singlets in 1 H NMR for their aromatic signals.…”

Section: Conformations Analysismentioning

confidence: 99%

Multiple Stimuli-Responsive Conformational Exchanges of Biphen[3]arene Macrocycle

et al. 2020

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Conformational exchanges of synthetic macrocyclic acceptors are rather fast, which is rarely studied in the absence of guests. Here, we report multiple stimuli-responsive conformational exchanges between two preexisting conformations of 2,2′,4,4′-tetramethoxyl biphen[3]arene (MeBP3) macrocycle. Structures of these two conformations are both observed in solid state, and characterized by 1H NMR, 13C NMR and 2D NMR in solution. In particular, conformational exchanges can respond to solvents, temperatures, guest binding and acid/base addition. The current system may have a role to play in the construction of molecular switches and other stimuli-responsive systems.

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“…Macrocyclic compounds and hosts, combining molecular recognition and complexation properties, have played a significant role in the development of supramolecular chemistry [ 1 , 2 , 3 , 4 , 5 , 6 ]. Renowned supramolecular hosts, such as crown ethers [ 7 , 8 ], cyclodextrins (CDs) [ 9 , 10 ], Stoddart’s “blue box” [ 11 ], calix[n]arenes [ 12 , 13 ], cucurbit[n]urils (CBs) [ 14 , 15 ], and pillar[n]arene [ 2 , 16 ] have been widely explored as building blocks for host–guest molecular recognition [ 17 , 18 ], energy storage [ 19 ], intelligent materials [ 20 , 21 , 22 , 23 ], drug delivery systems [ 24 , 25 , 26 , 27 ], and molecular machines [ 28 , 29 , 30 ], etc.…”

Section: Introductionmentioning

confidence: 99%

“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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Conformationally adaptive macrocycles with flipping aromatic sidewalls

Abstract:
Conformationally adaptive macrocycles possess multiple well-defined conformations through quickly flipping their aromatic sidewalls.

Cited by 78 publications

References 48 publications

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Multiple Stimuli-Responsive Conformational Exchanges of Biphen[3]arene Macrocycle

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

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Conformationally adaptive macrocycles with flipping aromatic sidewalls

Abstract: Conformationally adaptive macrocycles possess multiple well-defined conformations through quickly flipping their aromatic sidewalls.

Cited by 78 publications

References 48 publications

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Selection of Planar Chiral Conformations between Pillar[5,6]arenes Induced by Amino Acid Derivatives in Aqueous Media

Multiple Stimuli-Responsive Conformational Exchanges of Biphen[3]arene Macrocycle

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

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Abstract:
Conformationally adaptive macrocycles possess multiple well-defined conformations through quickly flipping their aromatic sidewalls.