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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 *** 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

Self-assembly of partially oxidized pillar[5]arenes induced by intermolecular charge transfer interactions

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Chinese Chemical Letters 2023年第12期34卷 220-224页

作者： Shuai Cao Leqian Song Huacheng Zhang Jie Han Yanli Zhao School of Chemical Engineering and Technology Xi'an Jjiaotong UniversityXi'an 710049China State Key Laboratory of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin 300071China School of Chemistry Chemical Engineering and BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Supramolecular interactions such as t-stacking interaction and charge transfer interaction have drawn much attention in the design and construction of various supramolecular ***,partially oxidized pillar[5]arene(P5A),pillar[4]arene[1]quinone(P4A1Q),pillar[3]arene[2]quinone(P3A2Q),and pillar[2]arene[3]quinone(P2A3Q)were synthesized by one-step *** indicated by experimental characterization data and density function theory modeling results,charge transfer interaction among partially oxidized P5A plays a significant role in host-host self-assembly behavior and corresponding packing *** work provides a unique strategy for the construction of functional macrocyclic assemblies through host-host self-assembly.

关键词： Charge transfer pillararenes Self-assembly Supramolecular chemistry Theoretical calculations

A meso–molecular muscle based on copillar[5]arenes

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Chinese Chemical Letters 2024年第3期35卷 308-311页

作者： Yu Yao Peiling Zhang Dan Zhou Zhinan Lai Shijun Li Feihe Huang Zibin Zhang College of Material Chemistry and Chemical EngineeringKey Laboratory of Organosilicon Chemistry and Material TechnologyMinistry of EducationKey Laboratory of Organosilicon Material TechnologyHangzhou Normal UniversityHangzhou 311121China Department of Chemistry Stoddart Institute of Molecular ScienceZhejiang UniversityHangzhou 310027China Green Catalysis Center and College of Chemistry Zhengzhou UniversityZhengzhou 450001China

A meso–molecular muscle was prepared by capping the[c2]daisy chain based on a mono-functionalized copillar[5]arene with an imidazolium group in its *** its crystal structure,we observed that it was a cyclic dimer composed of two mirror image subcomponents,a pR-and a pS-copillar[5]*** conformations were fixed by the doubly interlocked mechanical *** comparison of the^1H NMR and COSY spectra,we found that the length of this meso–molecular muscle could be controlled not only by the solvents,but also by the counter anions.

关键词： pillararenes Molecular muscles [c2]daisy chains Planar chirality

Complexation Selectivities of Pillar[5]arenes with Primary Ammonium Salts

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Chinese Journal of Chemistry 2013年第5期31卷 624-626页

作者： Luzhi Liu Yu Chen Lingyun Wang Herbert Meier Derong Cao School of Chemistry and Chemical Engineering State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou Guangdong 510641 China School of Chemistry and Chemical Engineering Guangxi University Nanning Guangxi 530004 China Institute of Organic Chemistry Johannes-Gutenberg-Universital Mainz D-55099 Mainz Germany

The complexation of alkyl-substituted pillar[5]arenes with primary ammonium salts is investigated. 1,4-Bis- （methoxy）pillar[5]arene （MeP5） can form strong complexes with the primary ammonium salts in CDC13. However, 1,4-bis（ethoxy）pillar[5]arene （EtP5） shows weak interaction with these guests, and 1,4-bis（butoxy）pillar[5]arene （BuP5） can not form such a complex at all. These results indicate that the modified alkyl chains of pillar[5]arene play an important role in the complexation selectivity.

关键词： pillararenes primary ammonium salts complexation selectivity host-guest chemistry bindingproperties

Naphthalene Diimide Templated Synthesis of Pillar[6]arenes

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Chinese Journal of Chemistry 2015年第3期33卷 339-342页

作者： Hua Ke Chen Jiao Yu-Heng Qian Mei-Jin Lin Jian-Zhong Chen College of Chemistry Fuzhou UniversityFuzhouFujian 350116China State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhouFujian 350002China

A facile method for the selective synthesis of pillar[6]arenes has been *** to a strong electron do-nor-acceptor interaction between the electron-deficient naphthalene diimide and a precursor for the pillararene,1,4-diisobutoxy-2,5-bis(methoxymethyl)benzene,naphthalene diimide has been demonstrated to act as a template for selective synthesis of pillar[6]arene in a modest yield(30%).

关键词： pillararenes naphthalene diimides templated synthesis donor-acceptor interactions

Crystal Structure and Host-Guest Binding Ability of Three Types of Pillar[5]arenes

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Chinese Journal of Chemistry 2015年第3期33卷 346-350页

作者： Luzhi Liu Wengui Duan Yuhui Kou Lingyun Wang Herbert Meier Derong Cao School of Chemistry and Chemical Engineering South China University of TechnologyGuangzhouGuangdong 510640China School of Chemistry and Chemical Engineering Guangxi UniversityNanningGuangxi 530004China Institute of Organic Chemistry University of MainzMainz 55099Germany

A systematic research of the structural characterization and the host-guest binding abilities between three types of pillar[5]arenes 3-5(3 for Structure Type I,4 for Structure Type II and 5 for Structure Type III)is carried out by 1H NMR measurements and X-ray *** results show that the configurations or symmetry of their cavities not only have large difference in these three types of pillar[5]arenes,but also have more or less variations even in the same structure type or the same host locked different guests such as crystals of 3a-3b,*** the other hand,the complexation behavior of pillar[5]arenes with 1,4-dibromobutane(DBB)is affected by the different symmetri-cal structure or substituents on the rings.

关键词： pillararenes crystal structure configuration complexation behavior

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 ***-based theranostic systems are of special interest in the biological and medical areas as they have shown very promising *** to easy preparation,reliable guest affinity,good biocompatibility and stability,pillararenes are frequently used to construct functional *** 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 *** 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 *** 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,*** introducing several typical examples,the design principles,preparation strategies,identifications and bio-applications of these pillararene-based supramolecular systems are *** challenges and directions of this field are also outlined.

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

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 *** 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 *** design a new diphenylanthracene derivative with two trimethylammonium bromide groups on both ends that can be well recognized by the pillar[5]*** formed nanocarriers can be used to load TPP through their supramolecular *** resulting nanoparticles show good water-solubility and uniform spherical *** 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 ***,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 *** 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

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