Stereoisomerism in Trimacrocyclic Structures Fused by a Pillar[6]arene and Two [8]Cycloparaphenylenes DOI

Hanchi Zhong,

Kai Lan,

Jiao Ming

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 13, 2025

Stereoisomerism in pillararenes, particularly chiral isomerism from atropisomers, has intrigued organic chemists. Herein, we report the synthesis and characterization of a trimacrocyclic system formed by fusing two [8]cycloparaphenylenes with pillar[6]arene. This exhibits unique stereoisomerism, yielding racemic mixture meso compound. The isomers were characterized using NMR, HRMS, single crystal X-ray diffraction. study offers valuable insights into constructing macrocycles enriches our understanding stereochemistry.

Language: Английский

Self‐Assembled Nanohelixes Driven by Host‐Guest Interactions and Metal Coordination DOI Open Access

Xin‐Yue Lou,

Kun Zhang,

Yujie Bai

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 20, 2024

Abstract Helical nanostructures fabricated via the self‐assembly of artificial motifs have been a captivating subject because their structural aesthetics and multiple functionalities. Herein, we report facile construction self‐assembled nanohelix ( NH ) by leveraging an achiral aggregation‐induced emission (AIE) luminogen G pillar[5]arene H ), driven host–guest interactions metal coordination. Inspired “sergeants soldiers” effect “majority rule” principle, complexation between is employed to fixate twisted conformation for generation “contortion sites”, which further induced emergence helicity as 1D assemblies are formed Ag(I) coordination hexagonally packed into nano‐sized fibers. The strategy has proved feasible in both homogeneous heterogeneous syntheses. Along with formation , boosted luminescence enhanced productivity reactive oxygen species (ROS) afforded efficient restriction on indicating concurrent regulation ′s morphology photophysical properties supramolecular assembly. In addition, also exhibits capacity bacteria imaging photodynamic antibacterial activities against Staphylococcus aureus S. Escherichia coli E. ).

Language: Английский

Citations

6

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

et al.

Deleted Journal, Journal Year: 2023, Volume and Issue: 2(1)

Published: Dec. 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.

Language: Английский

Citations

10

Thiacalixarene Carboxylic Acid Derivatives as Inhibitors of Lysozyme Fibrillation DOI Open Access
Anastasia Nazarova, Igor Shiabiev, K. S. Shibaeva

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(9), P. 4721 - 4721

Published: April 26, 2024

Amyloid fibroproliferation leads to organ damage and is associated with a number of neurodegenerative diseases affecting populations worldwide. There are several ways protect against fibril formation, including inhibition. A variety organic compounds based on molecular recognition amino acids within the protein have been proposed for design such inhibitors. However, role macrocyclic compounds, i.e., thiacalix[4]arenes, in inhibiting fibrillation still almost unknown. In present work, use water-soluble thiacalix[4]arene derivatives inhibition hen egg-white lysozyme (HEWL) amyloid first time. The binding HEWL by synthesized thiacalix[4]arenes (logKa = 5.05–5.13, 1:1 stoichiometry) formation stable supramolecular systems capable stabilizing structure protecting 29–45%. macrocycle conformation has little effect strength, native secondary does not change via interaction. non-toxic A549 cell line range 0.5–250 µg/mL. results obtained may be useful further investigation anti-amyloidogenic also open up future prospects creation new prevent diseases.

Language: Английский

Citations

4

Halogen bonding BODIPY-appended pillar[5]arene for the optical sensing of dicarboxylates and a chemical warfare agent simulant DOI Creative Commons
Andrew J. Taylor, Jamie T. Wilmore, Paul D. Beer

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A novel halogen bonding pillararene, decorated with BODIPY fluorescent reporter groups, demonstrated strong sensing of environmentally damaging dicarboxylates and a chemical warfare agent simulant in highly competitive aqueous-containing media.

Language: Английский

Citations

4

Macrocyclic Neutralizer to Polybrene via Direct Host–Guest Complexation DOI

Yahan Zhang,

Yu Xiang, Di Gao

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(12), P. 10425 - 10435

Published: June 7, 2024

Hexadimethrine bromide (HB), a synthetic polycationic species, was introduced to clinical practice as heparin antidote and recently used in gene therapy. However, HB causes various complications such severe red blood cells (RBCs) aggregation tissue damage. Herein, we have synthesized water-soluble quaterphen[3]arene containing multiple sulfonate moieties (SQP3) novel macrocyclic neutralizer reverse

Language: Английский

Citations

3

Design of Anti-Hund Organic Emitters Based on Heptazine DOI
Chengxi Sun,

Zhenli Guo,

Ying Zhong Tang

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: 16(44), P. 60648 - 60657

Published: Oct. 25, 2024

Hund's rule, which is powerful in governing the first excited states of closed-shell organic materials, can hardly be violated to get inverted singlet-triplet gap (INVEST) molecules with negative energy gaps (ΔEST), although INVEST materials have shown extraordinary photophysical properties and promising device performance especially light-emitting diodes. Here, we propose a facile strategy construct emissive by introducing different types substituents heptazine various modes, effectively tune ΔEST enlarged oscillator strength (f) for high fluorescence rate derivatives. Systematic computational studies show that double substitution electron-donating units another nonconjugated substituent hybrid mode most favorable way achieving slightly large f values; conjugated will compete make molecule deviate from feature. Especially, series high-performance heptazine-based emitters were constructed, exhibiting low -0.362 eV, up 0.0436, as well wide range emission color 339 716 nm. Also, designed predicted radiative rates 106 s-1, along efficient reverse intersystem crossing reaching 108 s-1. Importantly, figure merit (FM) was proposed parameter wholly evaluate emitters, highest FM 0.198 found triazine amine-substituted heptazine. These results highlight great potential chromophore constructing revealing fundamental structure-property understandings material design anti-Hund improved properties.

Language: Английский

Citations

3

Copper-Catalyzed Oxidative Arylation and Hydroxylation of Indolin-2-ones for Direct Construction of Tetrasubstituted Carbon Centers DOI
Tianyu Li, Linlin Xu, Di Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

This study introduces a novel methodology for the direct construction of tetrasubstituted centers, utilizing secondary C(sp3)–H and C(sp2)–H substrates, specifically indolin-2-ones indoles, through an innovative oxidative cross-coupling reaction. Facilitated by straightforward copper salt catalyst, this reaction proceeds efficiently at mild temperature 40 °C under operationally streamlined conditions. Emphasizing sustainability, method is notably enhanced employing air (molecular oxygen) as eco-friendly oxidant. In approach, not only serves terminal oxidant but also oxygen donor in synthesis oxygen-containing compounds.

Language: Английский

Citations

0

Sulfonatoproxylated cucurbit[7]urils as highly water-soluble and biocompatible excipients for solubilizing poorly soluble drugs and improving the bioavailability of indomethacin DOI
Peipei Liu, Jie Xing, Yue‐Yang Liu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110831 - 110831

Published: Jan. 1, 2025

Language: Английский

Citations

0

Construction of Supramolecular Polymer Network Elastomers Based on Pillar[5]arene/Alkyl Chain Host–Guest Interactions DOI
Qingyun Li, Kai Hu,

Shaoyu Xu

et al.

ACS Macro Letters, Journal Year: 2025, Volume and Issue: unknown, P. 120 - 128

Published: Jan. 11, 2025

As a special kind of supramolecular compound with many favorable properties, pillar[

Language: Английский

Citations

0

Ortho-Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents DOI
Yuxuan Xu, Runmei Li, Fang Liang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Ortho-functionalization of pillar[n]arenes has been a formidable challenge, partially due to the fragility their macrocyclic skeletons. In this concise report, we describe facile synthetic method for monoarylation/alkylation at position ortho oxime functionality in pillar[4]arene[1]benzoquinone monoxime (1) via addition Grignard reagents. The described enables creation various mono-ortho-alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.

Language: Английский

Citations

0