Recognition Site Modifiable Macrocycle: Synthesis, Functional Group Variation and Structural Inspection DOI Creative Commons

Linmeng Fan,

Min Du,

Lichun Kong

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(3), P. 1338 - 1338

Published: Jan. 31, 2023

Traditional macrocyclic molecules encode recognition sites in their structural backbones, which limits the variation of and thus, would restrict adjustment properties. Here, we report a new oligoamide-based macrocycle capable varying functional groups by post-synthesis modification on its backbone. Through six steps common reactions, parent (9) can be produced gram scale with an overall yield 31%. The 9 to vary are demonstrated producing four different macrocycles (10–13) distinct groups, 2-methoxyethoxyl (10), hydroxyl (11), carboxyl (12) amide (13), respectively. 1H NMR study suggests that structure these is consistent our design, i.e., forming hydrogen bonding network at both rims 1H-1H NOESY indicates located inside cavity macrocycles. At last, preliminary molecular shows 10 recognize n-octyl-β-D-glucopyranoside (14) chloroform.

Language: Английский

Photofunctional cyclophane host–guest systems DOI
Swadhin Garain, Frank Würthner

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This feature article presents cyclophane-based host–guest complexes for which electronic interactions between the host and guest molecules can modulate excited-state properties in an advanced way involving both singlet triplet excited states.

Language: Английский

Citations

2

The Story of the Little Blue Box: A Tribute to Siegfried Hünig DOI Creative Commons
Xiao‐Yang Chen, Hongliang Chen, J. Fraser Stoddart

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(1)

Published: Sept. 22, 2022

Abstract The tetracationic cyclophane, cyclobis(paraquat‐ p ‐phenylene), also known as the little blue box, constitutes a modular receptor that has facilitated discovery of many host–guest complexes and mechanically interlocked molecules during past 35 years. Its versatility in binding small π‐donors its state, well forming trisradical tricationic with viologen radical cations doubly reduced bisradical dicationic renders it valuable for construction various stimuli‐responsive materials. Since first reports 1988, box been featured over 500 publications literature. All this research activity would not have possible without seminal contributions carried out by Siegfried Hünig, who only pioneered syntheses viologen‐containing cyclophanes, but revealed their rich redox chemistry addition to ability undergo intramolecular π‐dimerization. This Review describes how his pioneering led design synthesis redox‐active host evolved into key component molecular shuttles, switches, machines.

Language: Английский

Citations

39

Platinum Metallacycle‐Based Molecular Recognition: Establishment and Application in Spontaneous Formation of a [2]Rotaxane with Light‐Harvesting Property DOI
Bingbing Shi, Xupeng Li,

Yongping Chai

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(31)

Published: June 7, 2023

Macrocyclic molecule-based host-guest systems, which provide contributions for the design and construction of functional supramolecular structures, have gained increasing attention in recent years. In particular, platinum(II) metallacycle-based systems opportunities chemical scientists to prepare novel materials with various functions structures due well-defined shapes cavity sizes metallacycles. However, research on has been given little attention. this article, we demonstrate complexation between a metallacycle polycyclic aromatic hydrocarbon molecule, naphthalene. Taking advantage interactions dynamic property reversible Pt coordination bonds, [2]rotaxane is efficiently prepared by employing template-directed clipping procedure. The further applied fabrication an efficient light-harvesting system multi-step energy transfer process. This work comprises important supplement macrocycle-based demonstrates strategy production mechanically interlocked molecules practical values.

Language: Английский

Citations

26

Assembly and Utility of a Drawstring‐Mimetic Supramolecular Complex DOI
Xiangyu Dong, Zhaoming Zhang, Hongyan Xiao

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(8)

Published: Jan. 2, 2024

Abstract Inspired by the drawstring structure in daily life, here we report development of a drawstring‐mimetic supramolecular complex at molecular scale. This consists rigid figure‐of‐eight macrocyclic host molecule and flexible linear guest which could interact through three‐point non‐covalent binding to form highly selective efficient host‐guest assembly. The not only resembles structure, but also mimics properties with regard deformations under external forces. can be utilized as an interlocked crosslinker for poly(methyl acrylate), corresponding polymer samples exhibit comprehensive enhancement macroscopic mechanical performance including stiffness, strength, toughness.

Language: Английский

Citations

11

Macrocycle‐based differential sensing: Design strategies and applications DOI Creative Commons

Jia‐Hong Tian,

Zhe Zheng, Yu‐Chen Pan

et al.

Deleted Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 26, 2025

Abstract Differential sensing, inspired by the olfactory systems in mammals, utilizes cross‐reactivity of multiple sensor units toward analytes to generate a distinctive fingerprint for each analyte. Widely acknowledged as robust analytical technique, differential sensing has entered flourishing era with advancement machine learning. Nevertheless, developing and optimizing signal transduction remain significant tasks left chemists. Macrocyclic receptors serve promising materials constructing arrays enhanced cross‐reactivity, facilitated their ease synthesis derivatization, inherent broad‐spectrum encapsulation capability, compatibility responsive approaches. Herein, we present concise overview fundamental processes involved array, encompassing array construction, transduction, data acquisition analysis, an emphasis on unique advantages provided macrocyclic former two aspects. Then, fascinating application scenarios where shine that rely various ingenious strategies. Finally, discuss several issues potential improvement future directions receptor‐based offering forward‐looking perspective.

Language: Английский

Citations

1

Supramolecular photosensitizers using extended macrocyclic hosts for photodynamic therapy with distinct cellular delivery DOI Creative Commons
Xiuli Zheng,

Sheng‐Nan Lei,

Zekun Gao

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(13), P. 3523 - 3530

Published: Jan. 1, 2023

The photosensitizers (PSs) for photodynamic therapy (PDT) mostly possess conjugated skeletons that are over-sized and poorly water-soluble to be encapsulated by conventional macrocyclic receptors. Herein, we report two fluorescent hydrophilic cyclophanes, AnBox·4Cl ExAnBox·4Cl, can effectively bind hypocrellin B (HB), a pharmaceutically active natural PS PDT, with binding constants of the 107 level in aqueous solutions. macrocycles feature extended electron-deficient cavities facilely synthesized through photo-induced ring expansions. corresponding supramolecular PSs (HB⊂AnBox4+ HB⊂ExAnBox4+) exhibit desirable stability, biocompatibility, cellular delivery, as well excellent PDT efficiency against cancer cells. In addition, living cell imaging results indicate HB⊂AnBox4+ HB⊂ExAnBox4+ have different delivery effects at level.

Language: Английский

Citations

17

Artificial molecular pumps DOI
Long Zhang, Huang Wu, Xuesong Li

et al.

Nature Reviews Methods Primers, Journal Year: 2024, Volume and Issue: 4(1)

Published: Feb. 22, 2024

Language: Английский

Citations

7

Tetraphenylethene-based macrocycles with dual-ring topology: synthesis, structures, and applications DOI
Junying Zhang, Wenbing Kang, Xing‐Dong Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6225 - 6239

Published: Jan. 1, 2023

This review focuses on the eight-shaped double ring structure of tetraphenylethylene, summarizes research progress structures, ionic molecular structures and metal looks forward to its future development direction.

Language: Английский

Citations

15

Artificial molecular machines: Design and observation DOI Creative Commons
Shu Zhang, Yi An, Xu‐Man Chen

et al.

Smart Molecules, Journal Year: 2023, Volume and Issue: 1(3)

Published: Oct. 23, 2023

Abstract Natural molecular machines have inspired the development of artificial machines, which potential to revolutionize several areas technology. Artificial commonly employ switches, motors, and shuttles as fundamental building blocks. The observation constructed by these blocks can be highly challenging due their small sizes intricate behaviors. use modern instrumentation advanced observational techniques plays a crucial role in characterization machines. Furthermore, well‐designed structure is also critical factor making more observable. This review summarizes common methods from diverse perspectives used observe emphasizes significance comprehending behaviors design superior

Language: Английский

Citations

13

Switchable molecular tweezers: design and applications DOI Creative Commons
Pablo Msellem,

Maksym Dekthiarenko,

Nihal Hadj Seyd

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 504 - 539

Published: March 1, 2024

Switchable molecular tweezers are a unique class of switches that, like their macroscopic analogs, exhibit mechanical motion between an open and closed conformation in response to stimuli. Such systems constitute essential component artificial machines. This review will present selected examples switchable potential applications. The first part be devoted chemically responsive tweezers, including stimuli such as pH, metal coordination, anion binding. Then, redox-active photochemical presented.

Language: Английский

Citations

5