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Development and Application of Chiral Materials
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Development and Application of Chiral Materials

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

Deadline for manuscript submissions: closed (31 January 2024) | Viewed by 6310

Special Issue Editor

Dr. Changlong Hao

E-Mail Website
Guest Editor
School of Food Science and Technology, Jiangnan University, Wuxi, China
Interests: chiral materials; synthesis; application
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent decades, chirality has been one of the core research topics of multidisciplinary research, encompassing materials science, chemistry, biology, and physics, etc. Recent advancements in chiral materials have focused on its asymmetry-breaking capability to construct molecular machines or macroscopic devices, to manipulate spins, electrons and photons with multi-degree of freedom, or to develop efficient drugs with low toxicity. Hence, it is timely and necessary to organize a Special Issue to comprehensively review the state-of-the-art development of chiral materials and prospective future research venues. The aim of this Special Issue is to summarize the recent developments and provide perspectives on a variety of topics related to chiral materials, including: the origin of symmetry breaking, stereoselective synthesis of functional materials, reconfigurable chirality, theory calculation or property prediction of chiral materials, and applications of chiral materials.

Dr. Changlong Hao
Guest Editor

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Keywords

  • chirality
  • nanoparticle
  • synthesis
  • application

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Published Papers (4 papers)

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Research

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19 pages, 3174 KiB  
Article
New Levan-Based Chiral Stationary Phases: Synthesis and Comparative HPLC Enantioseparation of (±)-trans-β-Lactam Ureas in the Polar Organic Mode
by Darko Kontrec, Mladenka Jurin, Andreja Jakas and Marin Roje
Molecules 2024, 29(10), 2213; https://doi.org/10.3390/molecules29102213 - 9 May 2024
Viewed by 887
Abstract
In this paper, the preparation of three new polysaccharide-type chiral stationary phases (CSPs) based on levan carbamates (3,5-dimethylphenyl, 4-methylphenyl, and 1-naphthyl) is described. The enantioseparation of (±)-trans-β-lactam ureas 1a–h was investigated by high-performance liquid chromatography (HPLC) on six different [...] Read more.
In this paper, the preparation of three new polysaccharide-type chiral stationary phases (CSPs) based on levan carbamates (3,5-dimethylphenyl, 4-methylphenyl, and 1-naphthyl) is described. The enantioseparation of (±)-trans-β-lactam ureas 1a–h was investigated by high-performance liquid chromatography (HPLC) on six different chiral columns (Chiralpak AD-3, Chiralcel OD-3, Chirallica PST-7, Chirallica PST-8, Chirallica PST-9, and Chirallica PST-10) in the polar organic mode, using pure methanol (MeOH), ethanol (EtOH), and acetonitrile (ACN). Apart from the Chirallica PST-9 column (based on levan tris(1-naphthylcarbamate), the columns exhibited a satisfactory chiral recognition ability for the tested trans-β-lactam ureas 1a–h. Full article
(This article belongs to the Special Issue Development and Application of Chiral Materials)
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15 pages, 2326 KiB  
Article
Optically Pure Calixarenyl Phosphine via Stereospecific Alkylation on Evans’ Oxazolidinone Moiety
by Claude Bauder and David Sémeril
Molecules 2024, 29(5), 1156; https://doi.org/10.3390/molecules29051156 - 5 Mar 2024
Viewed by 856
Abstract
A convenient protocol for the synthesis of 25,26,27-tribenzoyl-28-[((S)-1-diphenylphos- phanyl-propan-2-yl)oxy]-calix[4]arene via stereospecific methylation on Evans’ oxazolidinone moiety was reported. According to the 13C NMR analysis of this phosphine, the calix[4]arene skeleton adopted a 1,3-alternate conformation. The latter conformation of the macrocycle [...] Read more.
A convenient protocol for the synthesis of 25,26,27-tribenzoyl-28-[((S)-1-diphenylphos- phanyl-propan-2-yl)oxy]-calix[4]arene via stereospecific methylation on Evans’ oxazolidinone moiety was reported. According to the 13C NMR analysis of this phosphine, the calix[4]arene skeleton adopted a 1,3-alternate conformation. The latter conformation of the macrocycle and the (S)-chirality of the carbon atom bearing the methyl substituent were confirmed by a single-crystal X-ray diffraction study. After coordination of the phosphinated ligand to the dimeric [RuCl2(p-cymene)]2 organometallic precursor, the resulting arene–ruthenium complex was tested in the asymmetric reduction of acetophenone and alcohol was obtained with modest enantiomeric excess. Full article
(This article belongs to the Special Issue Development and Application of Chiral Materials)
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22 pages, 2566 KiB  
Article
Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpene 1,3-Aminoalcohol Regioisomers
by Dorottya Bai, Zsuzsanna Schelz, Mária Fanni Boncz, István Zupkó and Zsolt Szakonyi
Molecules 2023, 28(24), 7962; https://doi.org/10.3390/molecules28247962 - 5 Dec 2023
Viewed by 1203
Abstract
A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner–Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary aminoalcohol was formed via [...] Read more.
A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner–Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary aminoalcohol was formed via Raney-nickel-catalysed hydrogenation of an oxime, and a versatile library of aminoalcohols was synthesised using a Schiff base with the primary amines. The aminoalcohol regioisomers were prepared from the mesylate of the β-keto alcohols. The corresponding primary aminoalcohol was formed via the palladium-catalysed hydrogenation of hydroxyl-azide, and click reactions of the latter were also carried out. The new compounds were characterised using 1D- and 2D-NMR techniques and HRMS measurements. The in vitro investigations showed high inhibition of cell growth in human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231) in the case of naphthalic N-substituted derivatives. The antiproliferative effects were assayed using the MTT method. Full article
(This article belongs to the Special Issue Development and Application of Chiral Materials)
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Review

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18 pages, 4295 KiB  
Review
Interface Chirality: From Biological Effects to Biomedical Applications
by Liting Guo, Yanqiu Guo, Rui Wang, Jie Feng, Nannan Shao, Xiaolin Zhou and Yunlong Zhou
Molecules 2023, 28(15), 5629; https://doi.org/10.3390/molecules28155629 - 25 Jul 2023
Cited by 4 | Viewed by 2821
Abstract
Chiral surface is a critical mediator that significantly impacts interaction with biological systems on regulating cell behavior. To better understand how the properties of interfacial Chirality affect cell behavior and address the limitations of chiral materials for biomedical applications, in this review, we [...] Read more.
Chiral surface is a critical mediator that significantly impacts interaction with biological systems on regulating cell behavior. To better understand how the properties of interfacial Chirality affect cell behavior and address the limitations of chiral materials for biomedical applications, in this review, we mainly focus on the recent developments of chiral bio-interfaces for the controllable and accurate guidance of chiral biomedical phenomena. In particular, we will discuss how cells or organisms sense and respond to the chiral stimulus, as well as the chirality mediating cell fate, tissue repair, and organism immune response will be reviewed. In addition, the biological applications of chirality, such as drug delivery, antibacterial, antivirus and antitumor activities, and biological signal detection, will also be reviewed. Finally, the challenges of chiral bio-interfaces for controlling biological response and the further application of interface chirality materials for biomedical will be discussed. Full article
(This article belongs to the Special Issue Development and Application of Chiral Materials)
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