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Development and Application of Chiral Materials

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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 3839

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Special Issue Editor

Dr. Changlong Hao

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Guest Editor

School of Food Science and Technology, Jiangnan University, Wuxi 214122, China
Interests: chiral materials; synthesis; application

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

Published Papers (4 papers)

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Research

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19 pages, 3174 KiB

Open AccessArticle

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 319

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 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

Open AccessArticle

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 535

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 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

Open AccessArticle

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 854

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 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

Open AccessReview

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 2 | Viewed by 1694

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 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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