Alignment and Dynamic Inversion of Planar Chirality in Pillar[n]arenes DOI
Kenichi Kato, Shixin Fa, Tomoki Ogoshi

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(47)

Опубликована: Июль 31, 2023

Abstract Pillar[ n ]arenes are symmetrical macrocyclic compounds composed of benzene panels with para‐methylene linkages. Each panel usually exhibits planar chirality and prefers chirality‐aligned states. Because this feature, pillar[ attractive scaffolds for chiroptical materials that easy to prepare optically resolve show intense circular dichroism (CD) signals. In addition, rotation the endows a dynamic nature. The in tubular oligomers supramolecular assemblies sometimes time‐ procedure‐dependent alignment phenomena. Furthermore, CD signals some respond addition chiral guests when their is coupled host–guest properties. By using diastereomeric additional structures, response can also be caused by achiral changes environment, providing molecular sensors.

Язык: Английский

Chiral Adaptive Induction of an Achiral Cucurbit[8]uril‐Based Supramolecular Organic Framework by Dipeptides in Water DOI
Chaochao Yan, Qingfang Li, Xiaran Miao

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(37)

Опубликована: Июль 20, 2023

Chiral induction by natural biomolecules can reveal the indispensable role of chiral structures in life and be used to develop chirality-sensing biomolecular recognition. Here, we present synthesis characterization an achiral supramolecular organic framework (SOF-1) constructed from cucurbit[8]uril (CB[8]) hexaphenylbenzene (HPB) derivative (1) water. Due propeller-like rotational conformation HPB units specific recognition properties CB[8], SOF-1 demonstrates adaptive water when interacting with N-terminal Trp-/Phe-containing dipeptides including L-TrpX L-PheX (X is amino acid residue), respectively, exhibiting contrasting circular dichroism (CD) circularly polarized luminescence (CPL) spectra. Consequently, has been developed as a host chiroptical sensor capable recognizing distinguishing sequence-opposite dipeptide pairs L-TrpX/L-XTrp L-PheX/L-XPhe based on sequence-selective CD responses.

Язык: Английский

Процитировано

28

Alignment and Dynamic Inversion of Planar Chirality in Pillar[n]arenes DOI Creative Commons
Kenichi Kato, Shixin Fa, Tomoki Ogoshi

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(47)

Опубликована: Июль 31, 2023

Abstract Pillar[ n ]arenes are symmetrical macrocyclic compounds composed of benzene panels with para‐methylene linkages. Each panel usually exhibits planar chirality and prefers chirality‐aligned states. Because this feature, pillar[ attractive scaffolds for chiroptical materials that easy to prepare optically resolve show intense circular dichroism (CD) signals. In addition, rotation the endows a dynamic nature. The in tubular oligomers supramolecular assemblies sometimes time‐ procedure‐dependent alignment phenomena. Furthermore, CD signals some respond addition chiral guests when their is coupled host–guest properties. By using diastereomeric additional structures, response can also be caused by achiral changes environment, providing molecular sensors.

Язык: Английский

Процитировано

26

Pillararene-inspired arenes: Synthesis, properties and applications compared to the parent macrocycle DOI
Sem Bleus, Wim Dehaen

Coordination Chemistry Reviews, Год журнала: 2024, Номер 509, С. 215762 - 215762

Опубликована: Март 23, 2024

Язык: Английский

Процитировано

11

Engineering Helical Chirality in Metal-Coordinated Cyclodextrin Nanochannels DOI
Zhiyuan Jiang, Zhi Chen, Xiujun Yu

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер 147(9), С. 7325 - 7335

Опубликована: Фев. 18, 2025

Helicates are a defining element of DNAs and proteins, with functions that critical to variety biological processes. Cyclodextrins promising candidates for forging multiple-stranded helicates well-defined helicity, but lack available tools has precluded the construction artificial helical nanochannels controllable geometry helicity from these widely chiral building blocks. Herein, we disclose family Ag6L2 can be readily assembled α-cyclodextrin-derived ligands through coordination between pyridinyl groups Ag+ cations. We discovered exhibit either an M or P when cations adopt tetrahedral while losing most their linearly coordinated. Both precisely controlled by simply changing number methyl at ortho positions ligands. The tetracoordinated interconnect into infinite two-dimensional coordinative network characterized hexagonal tessellation. Theoretical calculations, which reveal lower energies conformations observed in crystals compared those inverted counterparts, support experimental results.

Язык: Английский

Процитировано

2

M/P Helicity Switching and Chiral Amplification in Double-Helical Monometallofoldamers DOI Creative Commons

Kotaro Matsumura,

K. Kinjo,

Kotaro Tateno

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(30), С. 21078 - 21088

Опубликована: Июль 19, 2024

Short-stranded double-helical monometallofoldamers capable of M/P-switching were constructed by the complexation two strands, each with L-shaped units linked a 2,2′-bipyridine, Zn(II) cation. The helix terminals "double-helical form" folded π–π interactions can unfold in solution to equilibrate "open forms" that are favored at higher temperatures. Interestingly, helical chirality chiral side chains induced single-handed sense and controlled depending on achiral solvent stimuli. For instance, (M)-helicity was nonpolarized solvents (toluene, hexane, Et2O), whereas (P)-helicity Lewis basic (acetone, DMSO). Circular dichroism (CD) rotating-frame overhauser enhancement spectroscopy (ROESY) measurements revealed conformational change due interaction double helices helicity bias. These novel possessed stable structure exhibited switchable chiroptical properties (gabs ∼ 10–3–10–2). In addition, strand transfer amplification abilities through formation heteroleptic when mixed an strand.

Язык: Английский

Процитировано

7

Functionalization of pillar[n]arenes towards optically responsive systems via host–guest interactions DOI
Keisuke Wada, Tomoki Ogoshi

Materials Chemistry Frontiers, Год журнала: 2023, Номер 8(5), С. 1212 - 1229

Опубликована: Дек. 9, 2023

In this review, we discuss progress in the field of pillar[ n ]arene-based optical response systems, focusing on color, fluorescence, circular dichroism, and circularly polarized luminescence signal changes via host–guest interactions.

Язык: Английский

Процитировано

11

Responsive pillar[n]arene materials DOI Creative Commons
De‐Hui Tuo, Tan‐Hao Shi, Shunsuke Ohtani

и другие.

Deleted Journal, Год журнала: 2023, Номер 2(1)

Опубликована: Дек. 30, 2023

Abstract Intelligent materials with responsive behaviors toward external stimuli, such as light, temperature, pH, redox, and solvent have been increasingly fascinating. Reversible noncovalent interactions provide an efficient way to construct stimuli‐responsive materials. Macrocyclic compounds, cyclodextrins, cucurbit[ n ]urils, calix[ ]arenes, crown ethers, related macrocycles, are useful skeletons for constructing through host–guest interactions. Pillar[ ]arenes pillar‐shaped macrocyclic hosts developed by our groups in 2008, which the repeated 1,4‐dialkoxybenzene units connected methylene bridges at para position. The versatile functionality, easy modification, excellent size‐dependent complexation, adjustable electron density of cavity endow pillar[ properties compared other cyclic host molecules. Moreover, unique planar chirality inversion generated unit rotation make ideal platforms investigating inversion, induction, transformation. In this review, we describe topological, optical, chiroptical, supramolecular assemblies, solid‐state based on complexation structural regulation ]arenes.

Язык: Английский

Процитировано

10

“Gear-driven”-type chirality transfer of tetraphenylethene-based supramolecular organic frameworks for peptides in water DOI Creative Commons
Chaochao Yan,

Qingfang Li,

Kaige Wang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(10), С. 3758 - 3766

Опубликована: Янв. 1, 2024

Chirality transfer for natural chiral biomolecules can reveal the indispensable role of structures in life and be used to develop chirality-sensing biomolecular recognition. Here, we report synthesis characterization a series achiral supramolecular organic frameworks (SOF-1, SOF-2, SOF-3), constructed from cucurbit[8]uril (CB[8]) tetraphenylethene (TPE) derivatives (1, 2, 3), respectively, as platforms explore their chirality mechanism peptides water. Given right-handed (P) left-handed (M) rotational conformation TPE units selective binding CB[8] aromatic amino acids, these SOFs selectively triggered water by containing N-terminal tryptophan (W) phenylalanine (F) residues into P- or M-rotational conformation, exhibiting significantly different circular dichroism (CD) spectra. Although various have same l-type configuration, they induce positive CD signals SOF-1 negative SOF-2 SOF-3, respectively. Based on structural analysis linkage between SOFs, "gear-driven"-type has been proposed visually illustrate multiple-step process recognition site CB[8]'s cavity units. Furthermore, utilizing characteristic generated through transfer, serve chiroptical sensor arrays effectively recognize distinguish based distinctive

Язык: Английский

Процитировано

4

Confined Space Nanoarchitectonics for Dynamic Functions and Molecular Machines DOI Creative Commons
Katsuhiko Ariga

Micromachines, Год журнала: 2024, Номер 15(2), С. 282 - 282

Опубликована: Фев. 17, 2024

Nanotechnology has advanced the techniques for elucidating phenomena at atomic, molecular, and nano-level. As a post nanotechnology concept, nanoarchitectonics emerged to create functional materials from unit structures. Consider material function when enables design of whose internal structure is controlled nanometer level. Material determined by two elements. These are that forms core environment (matrix) surrounds it. This review paper discusses confined space, which field controlling molecular machines. The first few sections introduce some various dynamic functions in spaces, considering biospace. In latter sections, examples research on behavior machines, such as motors, spaces discussed. particular, surface space nanospace taken up typical space. What these show not only central unit, but also surrounding spatial configuration necessary higher expression. Nanoarchitectonics will play important roles architecture total system.

Язык: Английский

Процитировано

3

Achieving strong and tunable circularly polarized luminescence through pillar[5]arenes insertion in BINOL-Py-based chromophore DOI
Xiaowei Qu, Zi‐Yuan Liu, Zhifan Wang

и другие.

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 111024 - 111024

Опубликована: Март 1, 2025

Язык: Английский

Процитировано

0