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Journal articles on the topic 'Pillar[n]arene'

Author: Grafiati

Published: 1 April 2023

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1

Xie, Changdong, Weibo Hu, Wenjing Hu, Yahu A. Liu, Jichuan Huo, Jiusheng Li, Biao Jiang, and Ke Wen. "Synthesis of Pillar[n]arene[5−n]quininesviaPartial Oxidation of Pillar[5]arene." Chinese Journal of Chemistry 33, no. 3 (March 2015): 379–83. http://dx.doi.org/10.1002/cjoc.201400895.

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2

Liu, Zhaona, Bing Li, Zhizheng Li, and Huacheng Zhang. "Pillar[n]arene-Mimicking/Assisted/Participated Carbon Nanotube Materials." Materials 15, no. 17 (September 3, 2022): 6119. http://dx.doi.org/10.3390/ma15176119.

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The recent progress in pillar[n]arene-assisted/participated carbon nanotube hybrid materials were initially summarized and discussed. The molecular structure of pillar[n]arene could serve different roles in the fabrication of attractive carbon nanotube-based materials. Firstly, pillar[n]arene has the ability to provide the structural basis for enlarging the cylindrical pillar-like architecture by forming one-dimensional, rigid, tubular, oligomeric/polymeric structures with aromatic moieties as the linker, or forming spatially “closed”, channel-like, flexible structures by perfunctionalizing with peptides and with intramolecular hydrogen bonding. Interestingly, such pillar[n]arene-based carbon nanotube-resembling structures were used as porous materials for the adsorption and separation of gas and toxic pollutants, as well as for artificial water channels and membranes. In addition to the art of organic synthesis, self-assembly based on pillar[n]arene, such as self-assembled amphiphilic molecules, is also used to promote and control the dispersion behavior of carbon nanotubes in solution. Furthermore, functionalized pillar[n]arene derivatives integrated carbon nanotubes to prepare advanced hybrid materials through supramolecular interactions, which could also incorporate various compositions such as Ag and Au nanoparticles for catalysis and sensing.

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3

Liu, Zhaona, Zhizheng Li, Bing Li, Le Zhou, Huacheng Zhang, and Jie Han. "Hybrid Macrocyclic Polymers: Self-Assembly Containing Cucurbit[m]uril-pillar[n]arene." Polymers 14, no. 9 (April 27, 2022): 1777. http://dx.doi.org/10.3390/polym14091777.

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Supramolecular self-assembly by hybrid macrocycles containing both cucurbit[m]uril (CB[m]) and pillar[n]arene was discussed and summarized in this review. Due to different solubility, diverse-sized cavities, and various driving forces in recognizing guests, the role of CB[m] and pillar[n]arene in such hybrid macrocyclic systems could switch between competitor in capturing specialized guests, and cooperator for building advanced hybridized macrocycles, by controlling their characteristics in host–guest inclusions. Furthermore, both CB[m] and pillar[n]arene were employed for fabricating advanced supramolecular self-assemblies such as mechanically interlocked molecules and supramolecular polymers. In those self-assemblies, CB[m] and pillar[n]arene played significant roles in, e.g., microreactor for catalyzing particular reactions to bridge different small pieces together, molecular “joint” to connect different monomers into larger assemblies, and “stabilizer” in accommodating the guest molecules to adopt a favorite structure geometry ready for assembling.

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4

Gorbachuk, Vladimir V., Anna R. Marysheva, and Ivan I. Stoykov. "Total oxidation of decahydroxypillar[5]arene with copper(II) and iron(III) nitrates." Butlerov Communications 63, no. 7 (July 31, 2020): 19–23. http://dx.doi.org/10.37952/roi-jbc-01/20-63-7-19.

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Pillar[n]arenes are suitable synthetic platforms for synthesis of functionalized p-cyclophanes, versatile building blocks for creating supramolecular polymers and (pseudo)rotaxanes. The presence of hydroquinone fragments in unsubstituted pillar[n]arene derivatives opens wide opportunities for their application in electrochemical sensors and for their use as reducing agents for synthesis of hybrid materials. Macrocyclic cavity plays the key role in molecular recognition, supramolecular self-assembly of pillararenes, and therefore possibility of switching electron donor properties of aromatic moieties, forming macrocyclic cavity presents specific interest. Synthesis of pillar[n]quinones is non-trivial goal, usually, it requires expensive reagents (сerium(IV) ammonium nitrate). As an oxidized compound alkoxy-derivatives of pillararenes are used. While possibility of red-ox transitions of decahydroxypillar[5]arene are well known, to the date in literature there are no examples of total oxidation of decahydroxypillar[5]arene. We have studied interaction of decahydroxy-pillar[5]arene with a row of inorganic oxidants: catalytic oxidation with air oxygen in presence of copper(II) and iron(III) nitrates, and oxidation with ammonium persulfate. In order to find the optimal conditions for oxidation of pillar[5]arene the series of solvents were tried (proton donor alcohols and acetic acid, proton acceptor dimethylformamide and dimethylsulfoxide). It was established that using glacial acetic acid as a solvent with ultrasonication leads to total oxidation of pillar[5]arene to pillar[5]quinone. This fact is explained by strong proton-donor properties of glacial acetic acid, to prevent formation of insoluble quinhydrone complexes of pillar[5]arene oxidation products. Using ammonium persulfate does not lead to the product of total oxidation.

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5

Liu, Zhaona, Bing Li, Leqian Song, and Huacheng Zhang. "Pillar[n]arene–calix[m]arene hybrid macrocyclic structures." RSC Advances 12, no. 43 (2022): 28185–95. http://dx.doi.org/10.1039/d2ra05118d.

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6

Khalil-Cruz, Laila E., Peiren Liu, Feihe Huang, and Niveen M. Khashab. "Multifunctional Pillar[n]arene-Based Smart Nanomaterials." ACS Applied Materials & Interfaces 13, no. 27 (June 29, 2021): 31337–54. http://dx.doi.org/10.1021/acsami.1c05798.

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7

Zhang, Huacheng, Zhaono Liu, Feifei Xin, and Aaiyou Hao. "Synthesis and Application of Pillar[n]arene." Chinese Journal of Organic Chemistry 32, no. 2 (2012): 219. http://dx.doi.org/10.6023/cjoc1107141.

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8

Xu, Xiaowen, Valentin Victor Jerca, and Richard Hoogenboom. "Structural Diversification of Pillar[ n ]arene Macrocycles." Angewandte Chemie International Edition 59, no. 16 (March 13, 2020): 6314–16. http://dx.doi.org/10.1002/anie.202002467.

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9

Ogoshi, Tomoki, Takahiro Kakuta, and Tada‐aki Yamagishi. "Applications of Pillar[ n ]arene‐Based Supramolecular Assemblies." Angewandte Chemie International Edition 58, no. 8 (February 18, 2019): 2197–206. http://dx.doi.org/10.1002/anie.201805884.

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10

Xiao, Tangxin, Lijie Qi, Weiwei Zhong, Chen Lin, Ruibing Wang, and Leyong Wang. "Stimuli-responsive nanocarriers constructed from pillar[n]arene-based supra-amphiphiles." Materials Chemistry Frontiers 3, no. 10 (2019): 1973–93. http://dx.doi.org/10.1039/c9qm00428a.

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11

Sathiyajith, CuhaWijay, Rafik Rajjak Shaikh, Qian Han, Yue Zhang, Kamel Meguellati, and Ying-Wei Yang. "Biological and related applications of pillar[n]arenes." Chemical Communications 53, no. 4 (2017): 677–96. http://dx.doi.org/10.1039/c6cc08967d.

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12

Mirzaei, Saber, Denan Wang, Sergey V. Lindeman, Camille M. Sem, and Rajendra Rathore. "Highly Selective Synthesis of Pillar[n]arene (n = 5, 6)." Organic Letters 20, no. 20 (October 10, 2018): 6583–86. http://dx.doi.org/10.1021/acs.orglett.8b02937.

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13

Khadieva, Alena, Vladimir Gorbachuk, Dmitriy Shurpik, and Ivan Stoikov. "Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions." Molecules 24, no. 9 (May 10, 2019): 1807. http://dx.doi.org/10.3390/molecules24091807.

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A multicyclophane with a core based on tris(2-aminoethyl)amine (TREN) linked by amide spacers to three fragments of pillar[5]arene was synthesized. The choice of the tris-amide core allowed the multicyclophane to bind to anion guests. The presence of three terminal pillar[5]arene units provides the possibility of effectively binding the colorimetric probe N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine (PhTz). It was established that the multicyclophane complexed PhTz in chloroform with a 1:1 stoichiometry (lgKa = 5.2 ± 0.1), absorbing at 650 nm. The proposed structure of the complex was confirmed by 1H-NMR spectroscopy: the amide group linking the pillar[5]arene to the TREN core forms a hydrogen bond with the PhTz imino-group while the pillararenes surround PhTz. It was established that the PhTz:tris-pillar[5]arene complex could be used as a colorimetric probe for fluoride, acetate, and dihydrogen phosphate anions due to the anion binding with proton donating amide groups which displaced the PhTz probe. Dye displacement resulted in a color change from blue to pink, lowering the absorption band at 650 nm and increasing that at 533 nm.

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14

Nierengarten, Iwona, Robert Deschenaux, and Jean-François Nierengarten. "From Pillar[n]arene Scaffolds for the Preparation of Nanomaterials to Pillar[5]arene-containing Rotaxanes." CHIMIA International Journal for Chemistry 70, no. 1 (February 24, 2016): 61–66. http://dx.doi.org/10.2533/chimia.2016.61.

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15

Ogoshi, Tomoki, Ryuta Sueto, Yukie Hamada, Kazuki Doitomi, Hajime Hirao, Yoko Sakata, Shigehisa Akine, Takahiro Kakuta, and Tada-aki Yamagishi. "Alkane-length sorting using activated pillar[5]arene crystals." Chemical Communications 53, no. 61 (2017): 8577–80. http://dx.doi.org/10.1039/c7cc04454b.

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16

Ye, Fengqing, Ruijin Wei, Lingyun Wang, Herbert Meier, and Derong Cao. "A pillar[5]arene-containing cross-linked polymer: synthesis, characterization and adsorption of dihaloalkanes and n-alkylene dinitriles." RSC Advances 6, no. 92 (2016): 89810–14. http://dx.doi.org/10.1039/c6ra15728a.

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17

Joseph, Roymon. "Pillar[n]arene Derivatives as Sensors for Amino Acids." ChemistrySelect 6, no. 14 (April 14, 2021): 3519–33. http://dx.doi.org/10.1002/slct.202100098.

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18

Li, Yong-Fu, Zheng Li, Qi Lin, and Ying-Wei Yang. "Functional supramolecular gels based on pillar[n]arene macrocycles." Nanoscale 12, no. 4 (2020): 2180–200. http://dx.doi.org/10.1039/c9nr09532b.

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19

Shurpik, D. N., P. L. Padnya, L. I. Makhmutova, L. S. Yakimova, and I. I. Stoikov. "Selective stepwise oxidation of 1,4-decamethoxypillar[5]arene." New Journal of Chemistry 39, no. 12 (2015): 9215–20. http://dx.doi.org/10.1039/c5nj01951f.

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20

Tan, Li-Li, Youlong Zhu, Hai Long, Yinghua Jin, Wei Zhang, and Ying-Wei Yang. "Pillar[n]arene-based supramolecular organic frameworks with high hydrocarbon storage and selectivity." Chemical Communications 53, no. 48 (2017): 6409–12. http://dx.doi.org/10.1039/c7cc03638h.

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21

Ogoshi, Tomoki, Daiki Yamafuji, Daisuke Kotera, Takamichi Aoki, Shuhei Fujinami, and Tada-aki Yamagishi. "Clickable Di- and Tetrafunctionalized Pillar[n]arenes (n = 5, 6) by Oxidation–Reduction of Pillar[n]arene Units." Journal of Organic Chemistry 77, no. 24 (December 10, 2012): 11146–52. http://dx.doi.org/10.1021/jo302283n.

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22

Kravets, Kateryna, Mykola Kravets, Helena Butkiewicz, Sandra Kosiorek, Volodymyr Sashuk, and Oksana Danylyuk. "Electrostatic co-assembly of pillar[n]pyridiniums and calix[4]arene in aqueous media." CrystEngComm 24, no. 12 (2022): 2213–16. http://dx.doi.org/10.1039/d2ce00232a.

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23

Tan, Li-Li, Youlong Zhu, Yinghua Jin, Wei Zhang, and Ying-Wei Yang. "Highly CO2 selective pillar[n]arene-based supramolecular organic frameworks." Supramolecular Chemistry 30, no. 7 (January 17, 2018): 648–54. http://dx.doi.org/10.1080/10610278.2018.1427239.

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24

Ogoshi, Tomoki, Ryuta Sueto, Kumiko Yoshikoshi, and Tada-aki Yamagishi. "One-dimensional channels constructed from per-hydroxylated pillar[6]arene molecules for gas and vapour adsorption." Chem. Commun. 50, no. 96 (2014): 15209–11. http://dx.doi.org/10.1039/c4cc06591c.

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We report that one-dimensional channels constructed from per-hydroxylated pillar[6]arene molecules with a diameter of 6.7 Å can capture various gases, such as CO₂, N₂ and n-butane, and vapours of saturated hydrocarbons such as n-hexane and cyclohexane.

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25

Sahu, Debashis, Kalyanashis Jana, and Bishwajit Ganguly. "The role of non-covalent interaction for the adsorption of CO2 and hydrocarbons with per-hydroxylated pillar[6]arene: a computational study." New Journal of Chemistry 41, no. 20 (2017): 12044–51. http://dx.doi.org/10.1039/c7nj01744h.

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26

Li, Kun-Ang, Zhuo Wang, Chang-Dong Xie, Tao Chen, Hui Qiang, Yahu A. Liu, Xue-Shun Jia, Wei-Bo Hu, and Ke Wen. "Unidirectional complexation of pillar[4]arene[1]benzoquinoneoxime with alkyl alcohols." Organic & Biomolecular Chemistry 17, no. 20 (2019): 4975–78. http://dx.doi.org/10.1039/c9ob00665f.

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Unidirectional binding between a pillar[4]arene[1]benzoquinoneoxime host and n-alkyl alcoholic guests was realized with the hydroxy heads of the guests in direct contact with the oxime group of the macrocyclic host.

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27

Jie, Kecheng, Ming Liu, Yujuan Zhou, Marc A. Little, Angeles Pulido, Samantha Y. Chong, Andrew Stephenson, et al. "Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[n]arene Crystals." Journal of the American Chemical Society 140, no. 22 (May 12, 2018): 6921–30. http://dx.doi.org/10.1021/jacs.8b02621.

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28

Aoyama, Yu, Yasuo Shimada, Shigehisa Akine, Tomoki Ogoshi, Takashi Takeda, Hironori Hoshino, and Tomoyuki Akutagawa. "Crystal structures and phase transition behaviors of pillar[n]arene crystals." Acta Crystallographica Section A Foundations and Advances 73, a2 (December 1, 2017): C711. http://dx.doi.org/10.1107/s2053273317088635.

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29

Lou, Xin‐Yue, and Ying‐Wei Yang. "Pillar[ n ]arene‐Based Supramolecular Switches in Solution and on Surfaces." Advanced Materials 32, no. 43 (September 13, 2020): 2003263. http://dx.doi.org/10.1002/adma.202003263.

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30

Gao, Bo, Li-Li Tan, Nan Song, Ke Li, and Ying-Wei Yang. "A high-yield synthesis of [m]biphenyl-extended pillar[n]arenes for an efficient selective inclusion of toluene and m-xylene in the solid state." Chemical Communications 52, no. 34 (2016): 5804–7. http://dx.doi.org/10.1039/c6cc01892k.

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[m]Bp-ExPnwith a rigid and nanometer-sized cavity, as an extended version of pillar[n]arene by replacing 1,4-dimethoxybenzene monomers with biphenyl entities, was successfully designed and synthesized. Intriguingly,[m]Bp-ExPnpossesses a wide array of potential applications in the purification of petrochemicals.

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31

Zhang, Yahan, Mengke Ma, Longming Chen, Xinbei Du, Zhao Meng, Han Zhang, Zhibing Zheng, Junyi Chen, and Qingbin Meng. "A Biocompatible Liquid Pillar[n]arene-Based Drug Reservoir for Topical Drug Delivery." Pharmaceutics 14, no. 12 (November 28, 2022): 2621. http://dx.doi.org/10.3390/pharmaceutics14122621.

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Advanced external preparations that possess a sustained-release effect and integrate few irritant elements are urgently needed to satisfy the special requirements of topical administration in the clinic. Here, a series of liquid pillar[n]arene-bearing varying-length oligoethylene oxide chains (OEPns) were designed and synthesized. Following rheological property and biocompatibility investigations, pillar[6]arene with triethylene oxide substituents (TEP6) with satisfactory cavity size were screened as optimal candidate compounds. Then, a supramolecular liquid reservoir was constructed from host–guest complexes between TEP6 and econazole nitrate (ECN), an external antimicrobial agent without additional solvents. In vitro drug-release studies revealed that complexation by TEP6 could regulate the release rate of ECN and afford effective cumulative amounts. In vivo pharmacodynamic studies confirmed the formation of a supramolecular liquid reservoir contributed to the accelerated healing rate of a S. aureus-infected mouse wound model. Overall, these findings have provided the first insights into the construction of a supramolecular liquid reservoir for topical administration.

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32

Liu, Yamin, Fang Zhou, Fan Yang, and Da Ma. "Carboxylated pillar[n]arene (n = 5–7) host molecules: high affinity and selective binding in water." Organic & Biomolecular Chemistry 17, no. 20 (2019): 5106–11. http://dx.doi.org/10.1039/c9ob00684b.

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33

Al-Azemi, Talal F., Mickey Vinodh, Abdirahman A. Mohamod, and Fatemeh H. Alipour. "Encapsulated dichloroethane-mediated interlocked supramolecular polymeric assembly of A1/A2-dihydroxy-octyloxy pillar[5]arene 1,2-dichloroethane monosolvate." Acta Crystallographica Section E Crystallographic Communications 74, no. 10 (September 25, 2018): 1471–74. http://dx.doi.org/10.1107/s2056989018013415.

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Crystals of 1-(1,4-dihydroxy)-2,3,4,5-(1,4-dioctyloxy)-pillar[5]arene, C99H158O10·C2H4Cl2, were grown from a 1,2-dicholoroethane/n-hexane solvent system. In the crystal, the encapsulated 1,2-dichloroethane solvent is stabilized by C—H...π interactions and mediates the formation of an interlocked supramolecular polymer via C—H...Cl interactions.

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34

Nazarova, Anastasia, Luidmila Yakimova, Darya Filimonova, and Ivan Stoikov. "Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes." International Journal of Molecular Sciences 23, no. 2 (January 11, 2022): 779. http://dx.doi.org/10.3390/ijms23020779.

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Novel monosubstituted pillar[5]arenes containing both amide and carboxyl functional groups were synthesized. Solid lipid nanoparticles based on the synthesized macrocycles were obtained. Formation of spherical particles with an average hydrodynamic diameter of 250 nm was shown for pillar[5]arenes containing N-(amidoalkyl)amide fragments regardless of their concentration. It was established that pillar[5]arene containing N-alkylamide fragments can form spherical particles with two different sizes (88 and 223 nm) depending on its concentration. Mixed solid lipid nanoparticles based on monosubstituted pillar[5]arenes and surfactant (dodecyltrimethylammonium chloride) were obtained for the first time. The surfactant made it possible to level the effect of the macrocycle concentration. It was found that various types of aggregates are formed depending on the macrocycle/surfactant ratio. Changing the macrocycle/surfactant ratio allows to control the charge of the particles surface. This controlled property will lead to the creation of molecular-scale porous materials that selectively interact with various types of substrates, including biopolymers.

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35

Lan, Shang, Shuaijun Zhan, Jiaming Ding, Jiaqi Ma, and Da Ma. "Pillar[n]arene-based porous polymers for rapid pollutant removal from water." Journal of Materials Chemistry A 5, no. 6 (2017): 2514–18. http://dx.doi.org/10.1039/c6ta09266g.

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36

Acikbas, Yaser, Mehmet Aksoy, Merve Aksoy, Damla Karaagac, Elif Bastug, Ahmed Nuri Kursunlu, Matem Erdogan, Rifat Capan, Mustafa Ozmen, and Mustafa Ersoz. "Recent progress in pillar[n]arene-based thin films on chemical sensor applications." Journal of Inclusion Phenomena and Macrocyclic Chemistry 100, no. 1-2 (March 28, 2021): 39–54. http://dx.doi.org/10.1007/s10847-021-01059-5.

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37

Ogoshi, Tomoki, Kazuki Demachi, Keisuke Kitajima, and Tada-aki Yamagishi. "Selective complexation of n-alkanes with pillar[5]arene dimers in organic media." Chemical Communications 47, no. 37 (2011): 10290. http://dx.doi.org/10.1039/c1cc14395f.

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38

Xiao, Xue-Dong, Jia-Qi Liu, Ya-Li Bai, Rui-Hua Wang, and Jun-Wen Wang. "Pillar[5]arene-based N-heterocyclic carbene ligand for Pd-catalysed Suzuki reaction." Journal of Inclusion Phenomena and Macrocyclic Chemistry 87, no. 1-2 (October 25, 2016): 29–36. http://dx.doi.org/10.1007/s10847-016-0673-5.

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39

Ogoshi, Tomoki, Naosuke Ueshima, Fumiyasu Sakakibara, Tada-aki Yamagishi, and Takeharu Haino. "Conversion from Pillar[5]arene to Pillar[6–15]arenes by Ring Expansion and Encapsulation of C60 by Pillar[n]arenes with Nanosize Cavities." Organic Letters 16, no. 11 (May 19, 2014): 2896–99. http://dx.doi.org/10.1021/ol501039u.

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40

Han, Chengyou, Zibin Zhang, Xiaodong Chi, Mingming Zhang, Guocan Yu, and Feihe Huang. "Synthesis of 1,4-Bis(n-propoxy)pillar[7]arene and Its Host-guest Chemistry." Acta Chimica Sinica 70, no. 17 (2012): 1775. http://dx.doi.org/10.6023/a12060296.

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41

Xiao, Tangxin, and Leyong Wang. "Recent advances of functional gels controlled by pillar[n]arene-based host–guest interactions." Tetrahedron Letters 59, no. 13 (March 2018): 1172–82. http://dx.doi.org/10.1016/j.tetlet.2018.02.028.

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42

Hirohata, Tomoki, Naoki Shida, Tomoki Ogoshi, Ikuyoshi Tomita, and Shinsuke Inagi. "(Digital Presentation) Facile Synthesis of Pillar[6]Quinone and Investigation of Its Electrochemical Properties." ECS Meeting Abstracts MA2022-01, no. 42 (July 7, 2022): 1839. http://dx.doi.org/10.1149/ma2022-01421839mtgabs.

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Pillar[n]arene (n: number of units), macrocyclic para-arylene methylene molecules, have attracted attention owing to their symmetrical structures, host-guest properties, and original supramolecular assembly characteristics.1 Similarly, their quinone counterparts, pillar[n]quinone (P[Q]n), are also fascinating macrocycles containing electron-deficient quinone units, and therefore have potential application for novel host-guest chemistry and redox active materials. A hexagonal molecule, pillar[6]quinone (P[Q]6), is expected to form densely packed structures and a candidate for organic active material but the synthesis of P[Q]6 still remains a challenge. We previously demonstrated that the electrochemical oxidation (1.0 V vs. SCE) of 1,4-dihydroxypillar[6]arene (P[HQ]6) in methanol afforded micrometer scale hexagonal cylindrical depositions on electrode surfaces, which were composed of partially oxidized P[HQ]6-m[Q]m (composed of both hydroquinone and benzoquinone units) aggregating via quinhydrone formation.2 In this work, we successfully synthesized P[Q]6 for the first time by oxidation of its hydroquinone precursor P[HQ]6. Electrochemical oxidation (1.2 V vs. SCE) of P[HQ]6 in methanol gave the similar hexagonal cylindrical crystal of P[Q]6 evidenced by single crystal X-ray diffraction, NMR and HRMS analyses. In the crystallographic data, all quinone moieties seem to have intermolecular CH-O interaction between adjacent macrocycles, resulting in the formation of a hexagonal packing structure. In addition, we also found that scalable synthesis of P[Q]6 was possible by chemical oxidation of P[HQ]6 with phenyliodine(III)bis(trifluoroacetate) in 1,1,1,3,3,3-hexafluoro-2-propanol. To understand the electrochemical properties and electron-transfer behavior of P[Q]6, various voltametric studies were carried out. We revealed that three electrons are injected first, followed by stepwise three one-electron reductions due to the electrostatic repulsion in the latter electron-transfer process. Reference T. Ogoshi, T. Yamagishi, Y. Nakamoto, Chem. Rev., 116, 7937 (2016). C. Tsuneishi, Y. Koizumi, R. Sueto, H. Nishiyama, K. Yasuhara, T. Yamagishi, T. Ogoshi, Tomita and S. Inagi, Chem. Commun., 53, 7454 (2017). T. Hirohata, N. Shida, H. Uekusa, N. Yasuda, H. Nishihara, T. Ogoshi, I. Tomita, S. Inagi, Chem. Commun., 57, 6360 (2021). Figure 1

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43

Fu, Wenming, Yangzheng Huang, Luyao Deng, Jiahao Sun, Shao-Lu Li, and Yunxia Hu. "Ultra-thin microporous membranes based on macrocyclic pillar[n]arene for efficient organic solvent nanofiltration." Journal of Membrane Science 655 (August 2022): 120583. http://dx.doi.org/10.1016/j.memsci.2022.120583.

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44

Fahmy, Sherif Ashraf, Asmaa Ramzy, Basma M. Saleh, and Hassan Mohamed El-Said Azzazy. "Stimuli-Responsive Amphiphilic Pillar[n]arene Nanovesicles for Targeted Delivery of Cancer Drugs." ACS Omega 6, no. 40 (September 30, 2021): 25876–83. http://dx.doi.org/10.1021/acsomega.1c04297.

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Nutaitis, Charles F., and Gordon W. Gribble. "A Simple Synthesis of a Pillar[n]arene Building Block – 1,4-bis(4-Bromobenzyl)benzene†." Organic Preparations and Procedures International 53, no. 4 (July 4, 2021): 422–25. http://dx.doi.org/10.1080/00304948.2021.1920789.

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Li, Yutong, Jia Wen, Jiangshan Li, Zejia Wu, Wei Li, and Kui Yang. "Recent Applications of Pillar[n]arene-Based Host–Guest Recognition in Chemosensing and Imaging." ACS Sensors 6, no. 11 (October 19, 2021): 3882–97. http://dx.doi.org/10.1021/acssensors.1c01510.

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Xiao, Xue-Dong, Ya-Li Bai, Jia-Qi Liu, and Jun-Wen Wang. "Synthesis of novel pillar[5]arene-based N -heterocyclic carbene ligands for Pd-catalysed Heck reactions." Tetrahedron Letters 57, no. 30 (July 2016): 3385–88. http://dx.doi.org/10.1016/j.tetlet.2016.06.083.

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Zhao, Meng, Changjun Li, Xiaotao Shan, Huijing Han, Qiuhua Zhao, Meiran Xie, Jianzhuang Chen, and Xiaojuan Liao. "A Stretchable Pillararene-Containing Supramolecular Polymeric Material with Self-Healing Property." Molecules 26, no. 8 (April 10, 2021): 2191. http://dx.doi.org/10.3390/molecules26082191.

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Abstract:

Constructing polymeric materials with stretchable and self-healing properties arise increasing interest in the field of tissue engineering, wearable electronics and soft actuators. Herein, a new type of supramolecular cross-linker was constructed through host-guest interaction between pillar[5]arene functionalized acrylate and pyridinium functionalized acrylate, which could form supramolecular polymeric material via photo-polymerization of n-butyl acrylate (BA). Such material exhibited excellent tensile properties, with maximum tensile strength of 3.4 MPa and strain of 3000%, respectively. Moreover, this material can effectively dissipate energy with the energy absorption efficiency of 93%, which could be applied in the field of energy absorbing materials. In addition, the material showed self-healing property after cut and responded to competitive guest.

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Xia, Binyuan, Jiuming He, Zeper Abliz, Yihua Yu, and Feihe Huang. "Synthesis of a pillar[5]arene dimer by co-oligomerization and its complexation with n-octyltrimethyl ammonium hexafluorophosphate." Tetrahedron Letters 52, no. 34 (August 2011): 4433–36. http://dx.doi.org/10.1016/j.tetlet.2011.06.065.

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Xiao, Chao, Wenting Liang, Wanhua Wu, Kuppusamy Kanagaraj, Yafen Yang, Ke Wen, and Cheng Yang. "Resolution and Racemization of a Planar-Chiral A1/A2-Disubstituted Pillar[5]arene." Symmetry 11, no. 6 (June 9, 2019): 773. http://dx.doi.org/10.3390/sym11060773.

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Butoxycarbonyl (Boc)-protected pillar[4]arene[1]-diaminobenzene (BP) was synthesized by introducing the Boc protection onto the A1/A2 positions of BP. The oxygen-through-annulus rotation was partially inhibited because of the presence of the middle-sized Boc substituents. We succeeded in isolating the enantiopure RP (RP, RP, RP, RP, and RP)- and SP (SP, SP, SP, SP, and SP)-BP, and studied their circular dichroism (CD) spectral properties. As the Boc substituent is not large enough to completely prevent the flip of the benzene units, enantiopure BP-f1 underwent racemization in solution. It is found that the racemization kinetics is a function of the solvent and temperature employed. The chirality of the BP-f1 could be maintained in n-hexane and CH2Cl2 for a long period at room temperature, whereas increasing the temperature or using solvents that cannot enter into the cavity of BP-f1 accelerated the racemization of BP-f1. The racemization kinetics and the thermodynamic parameters of racemization were studied in several different organic solvents.

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