Chirality transcription and amplification by [2]pseudorotaxanes

Kuwahara, Shunsuke; Chamura, Rie; Tsuchiya, Sho; Ikeda, Mari; Habata, Yoichi

doi:10.1039/c2cc38758a

Cited by 22 publications

(17 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This indicates the occurrence of chiroptical induction of the macrocycle 1 a through its complexation with L1 , a phenomenon often observed during complexation between an achiral species and a chiral molecule [ 50 ]. In supramolecular chemistry, host–guest interactions play a crucial role in determining how chirality is transferred from guest to host [ 51 ]. As discussed in Section 2.1 , the electron-rich cavity is prone to capturing a cationic component, such as the ammonium part of L1 .…”

Section: Resultsmentioning

confidence: 99%

Chiroptical Sensing of Amino Acid Derivatives by Host–Guest Complexation with Cyclo[6]aramide

Wang

Liu

et al. 2021

Molecules

View full text Add to dashboard Cite

A hydrogen-bonded (H-bonded) amide macrocycle was found to serve as an effective component in the host–guest assembly for a supramolecular chirality transfer process. Circular dichroism (CD) spectroscopy studies showed that the near-planar macrocycle could produce a CD response when combined with three of the twelve L-α-amino acid esters (all cryptochiral molecules) tested as possible guests. The host–guest complexation between the macrocycle and cationic guests was explored using NMR, revealing the presence of a strong affinity involving the multi-point recognition of guests. This was further corroborated by density functional theory (DFT) calculations. The present work proposes a new strategy for amplifying the CD signals of cryptochiral molecules by means of H-bonded macrocycle-based host–guest association, and is expected to be useful in designing supramolecular chiroptical sensing materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Chiroptical Sensing of Amino Acid Derivatives by Host–Guest Complexation with Cyclo[6]aramide

Wang

Liu

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“… 27 In this case, this chirality transfer would induce a preferential spatial arrangement of the two rings of the 2,2′-bipyrene moiety when the crown ether macrocycle is located around the ammonium unit as a result of the chiral environment created by the phenylalanine residue. 28 Therefore, one of the possible chiral conformations of the macrocycle should be preferentially formed due to that the energetic degeneration between both R and S enantiomeric conformations is now broken. Moreover, it is also expected the conformational flexibility of the 2,2′-bipyrene subunit in such supramolecular arrangement to be hampered, yielding a neat chiral configuration.…”

Section: Resultsmentioning

confidence: 99%

A [2]Rotaxane-Based Circularly Polarized Luminescence Switch

et al. 2019

View full text Add to dashboard Cite

A rotaxane-based molecular shuttle has been synthesized in which the switching of the position of a fluorescent macrocycle on the thread turns “on” or “off” the circularly polarized luminescence (CPL) of the system while maintaining similar fluorescence profiles and quantum yields in both states. The chiroptical activity relies on the chiral information transfer from an ammonium salt incorporating d - or l -phenylalanine residues as chiral stereogenic covalent units to an otherwise achiral crown ether macrocycle bearing a luminescent 2,2′-bipyrene unit when they interact through hydrogen bonding. Each enantiomeric thread induces CPL responses of opposite signs on the macrocycle. Upon addition of base, the switching of the position of the macrocycle to a triazolium group disables the chiral information transfer to the macrocycle, switching “off” the CPL response. The in situ switching upon several acid/base cycles is also demonstrated.

show abstract

“…CSI‐MS is effective for the detection of labile supramolecules in solution [24–27] . We performed CSI‐MS experiments by varying the Ag + content (0–2.0 equiv) in the presence of 1 , and the formation of complexes with different stoichiometries was confirmed (Figure S4).…”

Section: Figurementioning

confidence: 95%

“…CSI-MS is effective for the detection of labile supramolecules in solution. [24][25][26][27] We performed CSI-MS experiments by varying the Ag + content (0-2.0 equiv) in the presence of 1, and the formation of complexes with different stoichiometries was confirmed (Figure S4). The mass spectra of 1 with 1.0 equiv of Ag + was dominated by peaks for the 2:2 complex at m/z 1880, indicating that the species present was [1 2 Ag 2 (OTf)] + .…”

mentioning

confidence: 93%

Pentacyclic Nano‐Trefoil

Tsuruoka

Hayano

et al. 2020

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

Tetra‐armed cyclen (1) bearing two 4‐(4′‐pyridyl)benzyl and two 3,5‐difluorobenzyl groups and its Ag+ complexes were prepared and structurally characterized. The complexes formed between 1 and Ag+ undergoes a reversible structural transformation between a 2:2 dimeric complex and a 3:5 pentacyclic trefoil complex with changes in the Ag+/1 molar ratio. It was also revealed that the 3:5 trefoil complex could encapsulate benzene and [D6]benzene selectively in solid‐state. The benzene‐included structures are stabilized by C−H⋅⋅⋅F−C interactions between the benzene molecule and the ligand molecule.

show abstract

Chirality transcription and amplification by [2]pseudorotaxanes

Cited by 22 publications

References 28 publications

Chiroptical Sensing of Amino Acid Derivatives by Host–Guest Complexation with Cyclo[6]aramide

Chiroptical Sensing of Amino Acid Derivatives by Host–Guest Complexation with Cyclo[6]aramide

A [2]Rotaxane-Based Circularly Polarized Luminescence Switch

Pentacyclic Nano‐Trefoil

Contact Info

Product

Resources

About