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Tailoring two-dimensional surfaces with pillararenes based host-guest chemistry

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Chinese Chemical Letters 2020年第12期31卷 3095-3101页

作者： Run-Hao Li Junkai Ma Yue Sun Haibing Li Hubei Key Laboratory of Catalysis and Materials Science College of Chemistry and Material SciencesSouth-Central University for NationalitiesWuhan 430074China Hubei Key Laboratory of Wudang Local Chinese Medicine Research Department of ChemistrySchool ofPhannacyHubei University of MedicineShiyan 442000China Key Laboratory of Pesticide and Chemical Biology(CCNU) Ministry of EducationCollege of ChemistryCentral China Normal UniversityWuhan 430079China

The two-dimensional surfaces have been fueled by the infinite possibility they offe red fo r basic re search,and for novel technologies in nanoelectronics.To realize many of these promises,the effective strategies were to design and control their surface chemistry,which plays a vital role in determining the chemical and physical properties.Macrocyclic host-guest chemistry with the reversible noncovalent interactions between macrocyclic hosts and suitable guests can be readily used for constructing multifunctional surfaces.Macrocyclic pillararenes,possessed the unique structure,have attracted the attentions of researchers in recent years.This feature article covers the recent development of pillararene-based twodimensional inte rfaces,including the fabrication and function of the hybrid composite.The combination of pillararenes and materials platform exhibited the novel property because of the characte ristic of cavity of macrocyclic host and confined spaces of surfaces.We anticipate that this review will be helpful to the researchers working in the fields of supramolecular chemistry and materials science.

关键词： pillararenes Host-guest chemistry Two-dimensional surfaces

All-in-one functional supramolecular nanoparticles based on pillar[5]arene for controlled generation,storage and release of singlet oxygen

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Frontiers of Chemical Science and Engineering 2023年第3期17卷 307-313页

作者： Bing Lu Zhecheng Zhang Meiyu Qi Yuehua Zhang Hualing Yang Jin Wang Yue Ding Yang Wang Yong Yao College of Chemistry and Chemical Engineering Nantong UniversityNantong 226019China

The storage and controlled release of singlet oxygen(^(1)O_(2))have attracted increasing attention due to the wide application and microsecond lifetime of^(1)O_(2)in water.Herein we provide an integrated nanoplatform consisting of a diphenylanthracene derivative,a water-soluble pillar[5]arene and a photosensitizer tetrakis(4-hydroxyphenyl)porphyrin(TPP),that may provide the controlled generation,storage and release of singlet oxygen.We design a new diphenylanthracene derivative with two trimethylammonium bromide groups on both ends that can be well recognized by the pillar[5]arene.The formed nanocarriers can be used to load TPP through their supramolecular self-assembly.The resulting nanoparticles show good water-solubility and uniform spherical morphology.After laser irradiation(660 nm),the nanoparticles exhibit excellent ability for the generation and storage of^(1)O_(2).When the irradiated nanoparticles are heated above 80°C,^(1)O_(2)can be released from the system.Therefore,in this paper we pioneer the use of noncovalent interaction to integrate the diphenylanthracene derivatives and photosensitizers into one functional system,which provides a new strategy for the controlled generation,storage and release of singlet oxygen.We believe this groundbreaking strategy will have a great potential in providing necessary amounts of^(1)O_(2)for the photodynamic therapy of tumors in dark.

关键词： storage and controlled release of singlet oxygen supramolecular nanoparticles noncovalent interactions pillararenes diphenylanthracene photosensitizers

Pillar[6]arenes: From preparation, host-guest property to self-assembly and applications

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Chinese Chemical Letters 2023年第3期34卷 66-79页

作者： Ruowen Tang Yanpeng Ye Shajun Zhu Yang Wang Bing Lu Yong Yao School of Chemistry and Chemical Engineering Nantong UniversityNantong 226019China Department of Hepatobiliary and Pancreatic Surgery Affiliated Hospital of Nantong UniversityNantong 226001China

Pillar[n]arenes primarily comprise pillar[5]arenes and pillar[6]arenes, which belong to the new class of supramolecular macrocyclic hosts. Pillar[n]arenes have aroused wide attention because of their highly rigid and symmetrical architectures, controllable cavity size, and wide applications in a wide variety of areas. Although pillar[6]arene is difficult to synthesize, numerous studies have been conducted on it. In this review, the strategies to synthesize and functionalize pillar[6]arenes are investigated systematically.In addition, their host-guest properties in organic solvents and in aqueous solution are described. Moreover, pillar[6]arenes applied in different fields(e.g., molecular recognition, drug release, cancer therapy,and gas separation) are clarified. Hopefully, this study is capable of arousing more attention from increasing scientists to study large-cavity pillar[n]arenes.

关键词： pillararenes Host-guest interactions Drug release Cancer therapy Supramolecular chemistry

Artificial Water Channels—Progress Innovations and Prospects

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CCS Chemistry 2023年第2期5卷 279-291页

作者： Dan-Dan Su Mihail Barboiu Institut Européen des Membranes Adaptive Supramolecular Nanosystems GroupUniversity of MontpellierENSCM-CNRSMontpellier F-34095

The design of artificialwater channels(AWCs)aims to mimic natural proteins that effectively mediate the selective transport of water across the bilayer and artificial polymeric membranes.Currently,impressive progress on synthetic backbones,including selfassembled channels,helical unimolecular,and other functional organic molecules,has been made to provide artificial alternatives and applications in real systems for promising product development.In this review,several synthetic channels exploited during the last fewyears are summarized according to their backbone architecture for water transport and ion transport respectively,showing their potential as natural transporter analogs and the importance of AWCs for industrial,environmental,and medical applications.

关键词： artificial water channels self-assembly I-quartet channels pillararenes aquafoldamers water desalination

A stimuli-responsive pillar[5]arene-based hybrid material with enhanced tunable multicolor luminescence and ion-sensing ability

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National Science Review 2021年第6期8卷 60-69页

作者： Xin-Yue Lou Nan Song Ying-Wei Yang State Key Laboratory of Inorganic Synthesis and Preparative Chemistry International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC)College of ChemistryJilin University

Tunable luminescent materials are becoming more and more important owing to their broad application potential in various fields. Here we construct a pillar[5]arene-based hybrid material with stimuli-responsive luminescent properties and ion-sensing abilities from a pyridine-modified conjugated pillar[5]arene and a planar chromophore oligo(phenylenevinylene) upon coordination of Cd(II) metal cores. This new material not only shows an optimized luminescence due to the minimized π–π stacking and efficient charge transfer properties benefitting from the existence of pillar[5]arene rings, but also exhibits tunable multicolor emission induced by different external stimuli including solvent, ions and acid, indicating great application potential as a fluorescent sensory material, especially for Fe3+. With this pillar[5]arene-based dual-ligand hybrid material, valid optimization and regulation on the fluorescence of the original chromophore have been achieved, which demonstrates a plausible strategy for the design of tunable solid-state luminescent materials and also a prototypical model for the effective regulation of fluorescent properties of planarπ systems using synthetic macrocycle-based building blocks.

关键词： aggregation-induced emission supramolecular chemistry luminescent materials pillararenes macrocycles

Pillararene-based supramolecular systems for theranostics and bioapplications

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Science China Chemistry 2021年第5期64卷 688-700页

作者： Huangtianzhi Zhu Qi Li Laila E.Khalil-Cruz Niveen M.Khashab Guocan Yu Feihe Huang State Key Laboratory of Chemical Engineering Key Laboratory of Excited-State Materials of Zhejiang ProvinceDepartment of ChemistryZhejiang UniversityHangzhou 310027China Smart Hybrid Materials Laboratory(SHMs) Advanced Membranes and Porous Materials CenterKing Abdullah University of Science and Technology(KAUST)Thuwal 23955-6900Saudi Arabia Green Catalysis Center and College of Chemistry Zhengzhou UniversityZhengzhou 450001China

As an emerging type of important macrocycles for supramolecular chemistry,pillararenes and their derivatives have been widely studied and applied in numerous fields,which intensively promotes the development of chemistry,materials science and biology.Pillararene-based theranostic systems are of special interest in the biological and medical areas as they have shown very promising results.Owing to easy preparation,reliable guest affinity,good biocompatibility and stability,pillararenes are frequently used to construct functional biomaterials.On one hand,pillararenes can either be used individually or form diversiform self-assemblies such as micelles,nanoparticles and vesicles to increase water solubility and biocompatibility of drugs.On the other hand,it is promising to modify solid materials like framework materials,silica nanoparticles and graphene oxides with pillararene derivatives to enhance their functions and controllability.In this review,we summarize recent endeavors of pillararene-based supramolecular systems with theranostics and other biological applications comprising drug delivery/chemotherapy,photodynamic/photothermal therapy,antimicrobials,bioimaging,etc.By introducing several typical examples,the design principles,preparation strategies,identifications and bio-applications of these pillararene-based supramolecular systems are described.Future challenges and directions of this field are also outlined.

关键词： pillararenes self-assembly theranostics drug delivery supra-amphiphiles

An amphiphilic[2]biphenyl-extended pillar[6]arene:Synthesis,controllable self-assembly in water and application in cell-imaging

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中国化学快报:英文版 2023年第8期34卷 171-174页

作者： Tingting Chen Jian Wang Ruowen Tang Yuying Huang Qin Zhao Yong Yao School of Chemistry and Chemical Engineering Nantong UniversityNantong 226019China

Synthesis and functionalization of novel macrocyclic host molecules are important topics in supramolecular chemistry.In this work,the first amphiphilic[2]biphenyl-extended pillar[6]arene(AM-[2]BP-ExP6)was designed and synthesized with poly(ethylene glycol)chains as the hydrophilic tails and a rigid cavity as the hydrophobic core.Due to its amphiphilic nature,AM-[2]BP-ExP6 could self-assemble to stable fibers in water.What’s more,AM-[2]BP-ExP6 could associate with quaternary ammonium modified tetraphenylethylene guest(QTPE)to form a 2:1 host-guest complex,accompanied by significant enhanced fluorescence.Interestingly,different like AM-[2]BP-ExP6,AM-[2]BP-ExP6⊃QTPE host-guest complex selfassembled into fluorescent particles with diameter about 310 nm,the obtained fluorescent particles can be further employed in living cell imaging.

关键词： pillararenes Host-guest interactions Amphiphilic Self-assembly Cell-imaging

Synthesis of a Pillar[5]arene with Both Hydroxyl and Methoxycarbonyl-Methoxy Groups and Its Host-Guest Complexation with a Bis(imidazolium)Salt

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Chinese Journal of Chemistry 2014年第2期32卷 128-132页

作者： Mingguang Pan Min Xue Department of Chemistry Zhejiang UniversityHangzhouZhejiang 310027China

By the introduction of methoxycarbonyl-methoxy groups and hydroxyl groups into a pillar structure,a pillararene entirely with two types of functional groups was successfully prepared,which can form a stable 1∶1 compl... 详细信息

关键词： pillararenes functionalization bis(imidazolium) host-guest complexation self-assembly

Voltammetric Behavior of 1,4-Dimethoxypillar[m]arene[n]quinones

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Chinese Journal of Chemistry 2016年第9期34卷 861-865页

作者： Hina Saba Jianggen An Yong Yang Min Xue Yongsong Liu School of Science Zhejiang Sci-Tech University Hangzhou Zhejiang 310018 China

The electrochemical properties of a series of 1,4-dimethoxypillar[m]arene[n]quinones （DMP[m]A[n]Qs） and the interactions between individual quinone units have been investigated on glassy carbon electrode in acetonitrile. All the quinone units showed relative electron uptake behavior except 1,4-dimethoxypillar[5]quinones （DMP[5]Q）. The results have shown that the electrochemical behavior of the DMP[m]A[n]Qs is comparatively different from that of their related linear quinone analogues. The resultant properties were attributed to the close proximity of redox-active sites as well as the delocalization of electrons on the aromatic rings. Another aspect to be considered responsible for their electronic properties was suggested to be the electrostatic repulsions between adjacent quinone units in these complex structures. Current studies provide a better understanding on the voltammetric behavior of pillararene derivatives with different numbers of quinone units as well as their future scope in certain future electrochemical applications.

关键词： pillararenes pillarquinones cyclic voltammetry