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Four Pillar[5]arene Constitutional Isomers:Synthesis,Crystal Structures,and Host-Guest Complexation of Their Derivatives with Paraquat in Water

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Chinese Journal of Chemistry 2015年第3期33卷 356-360页

作者： Yujuan Zhou Yong Yao feihe huang State Key Laboratory of Chemical Engineering Department of ChemistryZhejiang UniversityHangzhouZhejiang 310027China

A pillar[5]arene prepared from monomer 1 has four constitutional *** these constitutional iso-mers have the same molecular formula,their other properties that we have investigated are more or less *** have different melting points,different NMR spectra and different crystal ***,the corre-sponding four anionic constitutional pillar[5]arene isomers derived from these four constitutional isomers showed different binding abilities with paraquat G in *** association constants of 3a⊃G,3b⊃G,3c⊃G and 3d⊃G were determined to be(3.33±0.46)×10^(4)L•mol^(−1),(5.00±0.63)×10^(4)L•mol^(−1),(3.33±0.28)×10^(4)L•mol^(−1),and(1.43±0.09)×10^(4)L•mol^(−1),respectively.

关键词： self-assembly pillararenes supramolecular chemistry host-guest systems paraquat

pH-Responsive Host-Guest Complexation between a Water-soluble Pillar[7]Arene and a 2,7-Diazapyrenium Salt and Its Application in Controllable Self-assembly

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Chinese Journal of Chemistry 2018年第1期36卷 59-62页

作者： Zhengtao Li Jie Yang feihe huang State Key Laboratory of Chemical Engineering Center for Chemistry of High- Performance & Novel Materials Department of Chemistry Zhejiang University Hangzhou Zhejiang 310027 China

A novel host-guest recognition motif based on a water-soluble pillar[7]arene （WP7） and a 2,7-diazapyrenium salt （DMDAP） was prepared. According to the integrated results of ^1H NMR, 2D NOESY, UV-vis spectroscopy and fluorescence titration experiments, we demonstrated that the molecular recognition of WP7 to DMDAP in water not only has high association constant but also has pH-responsiveness. Subsequently, we took advantage of this molecular recognition motif to fabricate a supra-amphiphile based on WP7 and an amphiphilic 2,7-diazapyrenium derivative DAPAC. Its controllable self-assembly in water was also investigated by means of TEM and DLS techniques.

关键词： pillararenes host-guest chemistry pH-responsiveness supra-amphiphiles self-assembly

Controllable macrocyclic supramolecular assemblies in aqueous solution

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Science China Chemistry 2018年第8期61卷 979-992页

作者： Yong Chen feihe huang Zhan-Ting Li Yu Liu State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University Tianjin 300071 China Co-Innovation Center of Chemistry and Chemical Engineering (Tianjin) Tianjin 300072 China State Key Laboratory of Chemical Engineering Center for Chemistry of High-Performance & Novel Materials Department of Chemistry Zhejiang University Hangzhou 310027 China Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials and Collaborative Innovation Centre of Chemistry for Energy Materials (iChEM) Fudan University Shanghai 200438 China

A series of macrocycles, including crown ethers, cyclodextrins, calixarenes, pillararenes and cucurbiturils, are well known to be able to associate various organic/inorganic/biological guest molecules and ions in their well-defined cyclic cavities to form stable host-guest complexes and supramolecular systems through the cooperative contributions of various non-covalent *** one or more functional groups are attached to the cavity of macrocycles or guest molecules, enhanced and/or controlled host-guest associations may take place, leading to not only improved host-guest binding abilities but also fascinating *** this review, some representative contributions in the construction of controllable macrocyclic supramolecular assemblies in aqueous solution are presented with an emphasis on the stimuli-responsive control manner and wide applications of this property.

关键词： macrocycle supramolecular assembly stimuli-responsive aqueous solution

Construction of Supramolecular Polymers Based on Host-Guest Recognition

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Chinese Journal of Chemistry 2020年第12期38卷 1473-1479页

作者： Xiaofan Ji Feng Wang Xuzhou Yan Shengyi Dong feihe huang Department of Chemistry Zhejiang UniversityHangzhouZhejiang 310027China

What is the most favorite and original chemistry developed in your research group?The establishment of two new types of host-guest recognition building blocks(21-crown-7/secondary ammonium salt and pillar[5]arene/alkyl chain)for supramolecular *** do you get into this specific field?Could you please share some experiences with our readers?I got my introduction to supramolecular chemistry during the postgraduate *** are many phenomena closely related to the weak non-covalent interactions in nature,such as the storage and transmission of genetic information through the DNA double helix *** by these fascinating natural phenomena,scientists try to use non-covalent Interactions to prepare many very complex self-assembled systems including supramolecular polymers from natural and artificially designed structural *** 1987,Lehn,Cram,and Pederson won the Nobel Prize for their contribution to supramolecular *** present,supramolecular chemistry has developed into an emerging discipline formed by the intersection of chemistry,physics,life sciences,materials science,and electronic engineering.

关键词： structure. crown intersection

Supramolecular control over thermo-responsive systems with lower critical solution temperature behavior

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Aggregate 2021年第1期2卷 35-47页

作者： Qiao Zhang Shengyi Dong Mingming Zhang feihe huang College of Chemistry and Chemical Engineering Hunan UniversityChangshaP.R.China State Key Laboratory for Mechanical Behavior of Materials Shaanxi International Research Center for Soft MatterSchool of Materials Science and EngineeringXi’an Jiaotong UniversityXi’anP.R.China State Key Laboratory of Chemical Engineering Center for Chemistry of High-Performance&Novel MaterialsDepartment of ChemistryZhejiang UniversityHangzhouP.R.China Green Catalysis Center and College of Chemistry Zhengzhou UniversityZhengzhouP.R.China Correspondence Shengyi DongCollege of Chemistry and Chemical EngineeringHunan UniversityChangsha 410082P.R.China

Lower critical solution temperature(LCST)is the critical temperature below which the solution is miscible for all compositions and above which the solution becomes a *** study of LCST properties has become a central research topic due to its profound impact on the applications of stimuli-responsive *** by the marriage between materials science and supramolecular chemistry,the introduction of supramolecular pairs and interactions into polymeric LCST systems is increasingly ***,supramolecular interactions provide precise control over LCST behavior in both water and organic ***,supramolecular interactions not only control or adjust LCST behavior(supramolecular interaction controlled LCST),but also induce LCST phase behavior in species lack of thermo-sensitive properties(supramolecular interaction induced LCST).In this review,we summarize the applications of supramolecular interactions in LCST *** examining the relationship between supramolecular interactions and LCST changes,we further discuss the differences between supramolecular interaction controlled LCST and supramolecular interaction induced *** hope this review will give our readers a snapshot on how the supramolecular interactions influence the LCST behavior in various systems,and benefit them with different applications.

关键词： host-guest interactions lower critical solution temperature molecular recognition phase separation supramolecular chemistry

Negatively charged crown ethers for binding paraquat in water

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Science China Chemistry 2010年第5期53卷 1073-1079页

作者： Wu, Ling Liu, Ming Chen, XiaoPeng Li, ShiJun huang, feihe Department of Chemistry Zhejiang University Hangzhou 310027 China College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou 310036 China

A water soluble negatively charged fluorescent 1,4-benzo-1,5-naphtho-36-crown-10-based host has been devised and *** shown by proton NMR,ESI mass spectrometry and UV-vis spectroscopy,it binds paraquat with a 1:1 stoichiometry and an association constant of 4.50(±0.02) ×103 M-1 in *** complexation with paraquat in water was further investigated by fluorescence emission *** results revealed that when paraquat was added to the water solution of the host,the fluorescence emission of the host was quenched by the charge transfer between the crown ether host and paraquat guest.A similar bis-p-phenylene-34-crown-10-based host was synthesized as a contrasting *** the naphthalene unit,the second host binds paraquat with a 1:1 stoichiometry and a lower association constant,1.04(±0.04) ×103 M-1,in *** demonstrated that the naphthalene unit could not only act as a strong fluorescence group but also improve the π-πstacking interactions between the host and guest.

关键词： crown ether pseudorotaxane paraquat fluorescent

Cyclic Ether Contaminant Removal from Water Using Nonporous Adaptive Pillararene Crystals via Host-Guest Complexation at the Solid-Solution Interface

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Research 2019年第1期2019卷 981-990页

作者： Yujuan Zhou Kecheng Jie Run Zhao Errui Li feihe huang State Key Laboratory of Chemical Engineering Center for Chemistry of High-Performance&Novel MaterialsDepartment of ChemistryZhejiang UniversityHangzhou 310027China

Te removal of soluble cyclic ether contaminants,such as dioxane and THF,produced in industrial chemical processes from water is of great importance for environmental protection and human *** we report that nonporous adaptive crystals of perethylated pillar[5]arene(EtP5)and pillar[6]arene(EtP6)work as adsorbents for cyclic ether contaminant removal via hostguest complexation at the solid-solution *** EtP6 crystals have the ability to adsorb dioxane from water with the formation of 1:2 host-guest complex crystals,while EtP5 crystals ***,both guest-free EtP5 and EtP6 crystals remove THF from water with EtP5 having a better *** is because EtP5 forms a 1:2 host-guest complex with THF via host-guest complexation at the solid-solution interface while EtP6 forms a 1:1 host-guest complex with ***6 also shows the ability to selectively remove dioxane from water even in the presence of ***,the reversible transitions between nonporous guestfree EtP5 and EtP6 structures and guest-loaded structures make them highly recyclable.

关键词： porous remove adsorbent

Supramolecular polymers fabricated by orthogonal self-assembly based on multiple hydrogen bonding and macrocyclic host–guest interactions

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Chinese Chemical Letters 2020年第1期31卷 1-9页

作者： Tangxin Xiao Ling Zhou Xiao-Qiang Sun feihe huang Chen Lin Leyong Wang School of Petrochemical Engineering Advanced Catalysis and Green Manufacturing Collaborative Innovation CenterChangzhou UniversityChangzhou 213164China State Key Laboratory of Chemical Engineering Center for Chemistry of High Performance&Novel MaterialsDepartment of ChemistryZhejiang UniversityHangzhou 310027China Key Laboratory of Mesoscopic Chemistry of MOE Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Supramolecular polymers constructed by orthogonal self-assembly based on multiple hydrogen bonding and macrocyclic host-guest interactions have received increasing attention due to their elegant structures,outstanding properties,and potential *** bonding endows these supramolecular polymers with good adaptability and reversibility,while macrocyclic host-guest interactions give them good selectivity and versatile ***,functional supramolecular polymers fabricated by these two highly specific,noninterfering interactions in an orthogonal way have shown wide applications in the fields of molecular machines,electronics,soft materials,*** this review,we discuss the recent advances of functional supramolecular polymers fabricated by orthogonal self-assembly based on multiple hydroge n bonding and host-guest *** particular,we focus on crown ether-and pillar[n]arene-based supramolecular polymers due to their compatibility with multiple hydrogen bonds in organic *** fabrication strategies,interesting properties,and potential applications of these advanced supramolecular materials are mainly concerned.

关键词： Supramolecular polymer Orthogonal self-assembly Hydrogen bonding Host-guest interactions Stimuli-responsiveness

Pillararenes as Versatile Building Blocks for Fluorescent Materials

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Accounts of Materials Research 2022年第6期3卷 658-668页

作者： huangtianzhi Zhu Qi Li Weijie Zhu feihe huang State Key Laboratory of Chemical Engineering Stoddart Institute of Molecular ScienceDepartment of ChemistryZhejiang UniversityHangzhou 310027China Green Catalysis Center and College of Chemistry Zhengzhou UniversityZhengzhou 450001China

Fluorescent materials have received more and more attention in the past few decades because of their great potentials in the fields of luminescent devices,sensing,data storage,bioimaging,and other optical *** materials comprising organic molecules are of broad interest owing to their highly tunable *** studies on organic fluorescent materials were mainly focused on the design and covalent modification of fluorophores in order to improve their photophysical properties at the molecular level,whereas in recent decades,many studies have revealed that the intermolecular or intramolecular noncovalent interactions also play a crucial role in *** example,the modulation of noncovalent interactions in aggregates and selfassemblies was proven to be capable of adjusting aggregation-induced emission(AIE)-active fluorophores by the restriction of intramolecular motions(RIM).In addition,in the crystalline state,intermolecular noncovalent interactions are able to promote phosphorescence by decreasing nonradiative *** supramolecular macrocycles into organic fluorescent materials is an intriguing prospect because multiple noncovalent interactions are *** one hand,the photophysical properties of fluorophores can be changed upon inclusion within the macrocycles,providing unforeseen *** the other hand,the dynamic and reversible features of host−guest recognition endow the materials with controllability and stimuli-responsiveness,which is beneficial to the fabrication of smart *** numerous supramolecular macrocycles,pillararenes are promising candidates that can be included in fluorescent *** advantages of pillararenes are their easy functionalization and planar *** modification with proper substituents,pillararene derivatives possess high solubility and stability in both organic and aqueous media,and reversible guest binding *** features make pillararenes vers

关键词： materials Fluorescent aggregation