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Novel Synthetic Macrocycles: Synthesis, Structures, Properties and Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Macromolecular Chemistry".

Deadline for manuscript submissions: 30 April 2025 | Viewed by 3641

Special Issue Editor

Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Interests: supramolecular chemistry; organic chemistry; porous organic polymers

Special Issue Information

Dear Colleagues,

Since the serendipitous discovery of crown ethers by Pedersen at DuPont more than a half century ago, synthetic macrocycles have played a vital role in supramolecular and macrocyclic chemistry as they not only serve as indispensable tools for molecular recognition in host–guest chemistry but can also be utilized as important building blocks for the construction of supramolecular assemblies. Moreover, because of their unique structural features, easy functionalization, abundant host–guest complexation properties and dynamic reversible self-assembly, synthetic macrocycles have been widely applied in many research areas. Although various macrocyclic hosts have been reported during recent decades, the design and construction of new kinds of macrocyclic hosts with unique structures and specific properties are always one of the most important and frontier research topics in the areas of supramolecular and macrocyclic chemistry.

In this Special Issue, we will focus on the synthesis, structures, properties and applications of novel synthetic macrocycles. Particular attention will be paid to the development of new host-guest systems based on macrocycles and the exploration of their applications in more areas.

Dr. Ying Han
Guest Editor

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Keywords

  • macrocycles
  • supramolecular chemistry
  • host–guest chemistry
  • synthesis
  • applications

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Published Papers (2 papers)

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Research

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16 pages, 4379 KiB  
Article
Chirality Sensing of Amino Acid Esters by S-2-Methylbutanamido-Substituted m-Phthalic Diamide-Linked Zinc Bisporphyrinate
by Zhipeng Li, Yue Zhao, Yong Wang, Wen-Hua Zhang and Chuanjiang Hu
Molecules 2024, 29(15), 3652; https://doi.org/10.3390/molecules29153652 - 1 Aug 2024
Cited by 1 | Viewed by 897
Abstract
To understand the role of an additional coordination site in the linker in chirality sensing, we designed and synthesized an S-2-methylbutanamido-substituted m-phthalic diamide-linked zinc bisporphyrinate, [Zn2(S-MAABis)] and investigated its ability to sense the chirality of amino acid esters. The 1 [...] Read more.
To understand the role of an additional coordination site in the linker in chirality sensing, we designed and synthesized an S-2-methylbutanamido-substituted m-phthalic diamide-linked zinc bisporphyrinate, [Zn2(S-MAABis)] and investigated its ability to sense the chirality of amino acid esters. The 1H NMR spectra and the crystal structure showed that the amido oxygen adjacent to the chiral carbon was coordinated with zinc. NMR and UV–vis titration showed that the binding of [Zn2(S-MAABis)] to amino acid esters occurred via two equilibria, forming 1:1 and 1:2 host–guest complexes. The CD spectra suggested that [Zn2(S-MAABis)] can effectively recognize the absolute configuration of amino acid esters. The sign of the CD spectra remained unchanged during the titration, indicating that the corresponding 1:1 and 1:2 host–guest complexes had the same chirality. This is different from previously studied amino-substituted m-phthalic diamide-linked zinc bisporphyrinate [Zn2(AmBis)], which showed chirality inversion during titration. Theoretical calculations indicated that the additional coordination sites (amido or amino) in the 1:1 host–guest complexes played different roles, leading to differences in chirality. Our studies suggest that the introduction of a coordination site can influence the chirality transfer process, but the results of chirality transfers are dependent on the specific binding modes. Full article
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Review

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32 pages, 84279 KiB  
Review
Macrocycle-Based Supramolecular Drug Delivery Systems: A Concise Review
by Yanrui Yang, Pengcheng Li, Haibo Feng, Rui Zeng, Shanshan Li and Qixiong Zhang
Molecules 2024, 29(16), 3828; https://doi.org/10.3390/molecules29163828 - 12 Aug 2024
Viewed by 2446
Abstract
Efficient delivery of therapeutic agents to the lesion site or specific cells is an important way to achieve “toxicity reduction and efficacy enhancement”. Macrocycles have always provided many novel ideas for drug or gene loading and delivery processes. Specifically, macrocycles represented by crown [...] Read more.
Efficient delivery of therapeutic agents to the lesion site or specific cells is an important way to achieve “toxicity reduction and efficacy enhancement”. Macrocycles have always provided many novel ideas for drug or gene loading and delivery processes. Specifically, macrocycles represented by crown ethers, cyclodextrins, cucurbit[n]urils, calix[n]arenes, and pillar[n]arenes have unique properties, which are different cavity structures, good biocompatibility, and good stability. Benefited from these diverse properties, a variety of supramolecular drug delivery systems can be designed and constructed to effectively improve the physical and chemical properties of guest molecules as needed. This review provides an outlook on the current application status and main limitations of macrocycles in supramolecular drug delivery systems. Full article
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