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Journal articles on the topic 'Cycloparaphenylenes'

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Author: Grafiati

Published: 10 March 2023

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1

D'Auria, Maurizio. "The Use of D Index in the Estimation of Aromaticity: The Case of Cycloparaphenylene." Letters in Organic Chemistry 16, no. 2 (January 9, 2019): 134–38. http://dx.doi.org/10.2174/1570178615666180830113618.

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Cycloparaphenylenes are important compounds for their photophysical and electronic properties. The curved structure of these compounds induces an alteration of the aromatic character of these compounds. D values have been used to describe the aromatic character of compounds from [5]- to [10]cycloparaphenylene. D values are compared with HOMED and with the strain energy are obtained by using an homodesmotic reaction.

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2

Lewis, Simon E. "Cycloparaphenylenes and related nanohoops." Chemical Society Reviews 44, no. 8 (2015): 2221–304. http://dx.doi.org/10.1039/c4cs00366g.

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Cyclic oligo-para-phenylenes (“CPPs”) possessing radial π systems have markedly different properties to the analogous linear oligo-para-phenylenes. Their synthesis is challenging due to the strain inherent in their structures, but several distinct strategies to access them have now been described. This review describes the synthesis, properties and applications of CPPs and related variants.

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3

Oldani, N., S. K. Doorn, S. Tretiak, and S. Fernandez-Alberti. "Photoinduced dynamics in cycloparaphenylenes: planarization, electron–phonon coupling, localization and intra-ring migration of the electronic excitation." Physical Chemistry Chemical Physics 19, no. 45 (2017): 30914–24. http://dx.doi.org/10.1039/c7cp06426h.

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4

Alvarez, Miriam Peña, M. Carmen Ruiz Delgado, Mercedes Taravillo, Valentín G. Baonza, Juan T. López Navarrete, Paul Evans, Ramesh Jasti, Shigeru Yamago, Miklos Kertesz, and Juan Casado. "The Raman fingerprint of cyclic conjugation: the case of the stabilization of cations and dications in cycloparaphenylenes." Chem. Sci. 7, no. 6 (2016): 3494–99. http://dx.doi.org/10.1039/c6sc00765a.

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5

Sisto, Thomas J., Lev N. Zakharov, Brittany M. White, and Ramesh Jasti. "Towards pi-extended cycloparaphenylenes as seeds for CNT growth: investigating strain relieving ring-openings and rearrangements." Chemical Science 7, no. 6 (2016): 3681–88. http://dx.doi.org/10.1039/c5sc04218f.

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6

Fujitsuka, Mamoru, Eiichi Kayahara, Chao Lu, Shigeru Yamago, and Tetsuro Majima. "Significant structural relaxations of excited [n]cycloparaphenylene dications (n = 5–9)." Physical Chemistry Chemical Physics 20, no. 46 (2018): 29207–11. http://dx.doi.org/10.1039/c8cp04860f.

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7

Dang, Jing-Shuang, Wei-Wei Wang, Xiang Zhao, and Shigeru Nagase. "A mechanistic study on cationic Li prompted Diels–Alder cycloaddition of cycloparaphenylene." Organic Chemistry Frontiers 4, no. 9 (2017): 1757–61. http://dx.doi.org/10.1039/c7qo00290d.

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8

Griwatz, Jan H., and Hermann A. Wegner. "One-Pot Synthesis of Cycloparaphenylenes." Organic Materials 02, no. 04 (October 2020): 306–12. http://dx.doi.org/10.1055/s-0040-1721082.

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The preparation of cycloparaphenylenes ([n]CPPs) with their bent π-system poses a long-standing challenge in organic synthesis. In the current multi-step approaches to access CPPs, pre-angulated precursors were combined using transition metal-catalysed or mediated coupling reactions. Therefore, there is a long way to the realisation of the idea of an ‘ideal synthesis’. An easy and efficient synthesis of different [n]CPPs would represent a breakthrough, also pushing their incorporation into organic materials. By combining multiple steps in a one-pot approach, the overall time and workload can be drastically shortened. Herein, we present the application of this concept for the preparation of [6] and [9]CPP as a simple and fast alternative to current methods. By tuning the reaction conditions the selective synthesis of both [6] and [9]CPP was demonstrated.

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9

Wassy, Daniel, Mathias Hermann, Jan S. Wössner, Lucas Frédéric, Grégory Pieters, and Birgit Esser. "Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs." Chemical Science 12, no. 30 (2021): 10150–58. http://dx.doi.org/10.1039/d1sc02718b.

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10

Jiang, Yuhang, Edoardo Jun Mattioli, Matteo Calvaresi, and Zhiyong Wang. "Theoretical design of an ultrafast supramolecular rotor composed of carbon nano-rings." Chemical Communications 56, no. 79 (2020): 11835–38. http://dx.doi.org/10.1039/d0cc04806b.

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11

Zhou, Zheng, Zheng Wei, Tobias A. Schaub, Ramesh Jasti, and Marina A. Petrukhina. "Structural deformation and host–guest properties of doubly-reduced cycloparaphenylenes, [n]CPPs2− (n = 6, 8, 10, and 12)." Chemical Science 11, no. 35 (2020): 9395–401. http://dx.doi.org/10.1039/d0sc03072d.

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12

Rio, J., D. Erbahar, M. Rayson, P. Briddon, and C. P. Ewels. "Cyclotetrahalo-p-phenylenes: simulations of halogen substituted cycloparaphenylenes and their interaction with C60." Physical Chemistry Chemical Physics 18, no. 33 (2016): 23257–63. http://dx.doi.org/10.1039/c6cp03376h.

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13

Bachrach, Steven M., and Henry S. Rzepa. "Cycloparaphenylene Möbius trefoils." Chemical Communications 56, no. 88 (2020): 13567–70. http://dx.doi.org/10.1039/d0cc04190d.

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DFT computations (ωB97X-D/6-31G(d)) of eight different cycloparaphenylenes that have three internal linking groups are shown to have two different conformations that express interesting Möbius topologies.

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14

Hirst, Elizabeth S., and Ramesh Jasti. "Bending Benzene: Syntheses of [n]Cycloparaphenylenes." Journal of Organic Chemistry 77, no. 23 (November 13, 2012): 10473–78. http://dx.doi.org/10.1021/jo302186h.

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15

Kayahara, Eiichi, Yao Cheng, and Shigeru Yamago. "Short-step Synthesis of Large Cycloparaphenylenes." Chemistry Letters 47, no. 9 (September 5, 2018): 1108–11. http://dx.doi.org/10.1246/cl.180486.

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16

Bachrach, Steven M., and Zeina-Christina Zayat. "“Planetary Orbit” Systems Composed of Cycloparaphenylenes." Journal of Organic Chemistry 81, no. 11 (May 17, 2016): 4559–65. http://dx.doi.org/10.1021/acs.joc.6b00339.

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17

Nishihara, Taishi, Yasutomo Segawa, Kenichiro Itami, and Yoshihiko Kanemitsu. "Exciton recombination dynamics in nanoring cycloparaphenylenes." Chemical Science 5, no. 6 (2014): 2293. http://dx.doi.org/10.1039/c3sc53462f.

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18

Lewis, Simon E. "ChemInform Abstract: Cycloparaphenylenes and Related Nanohoops." ChemInform 46, no. 27 (June 18, 2015): no. http://dx.doi.org/10.1002/chin.201527279.

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19

Kubota, Natsumi, Yasutomo Segawa, and Kenichiro Itami. "η6-Cycloparaphenylene Transition Metal Complexes: Synthesis, Structure, Photophysical Properties, and Application to the Selective Monofunctionalization of Cycloparaphenylenes." Journal of the American Chemical Society 137, no. 3 (January 17, 2015): 1356–61. http://dx.doi.org/10.1021/ja512271p.

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20

Darzi, Evan R., and Ramesh Jasti. "The dynamic, size-dependent properties of [5]–[12]cycloparaphenylenes." Chemical Society Reviews 44, no. 18 (2015): 6401–10. http://dx.doi.org/10.1039/c5cs00143a.

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21

Li, Ke, Zhanqiang Xu, Han Deng, Zhennan Zhou, Yanfeng Dang, and Zhe Sun. "Dimeric Cycloparaphenylenes with a Rigid Aromatic Linker." Angewandte Chemie International Edition 60, no. 14 (February 26, 2021): 7649–53. http://dx.doi.org/10.1002/anie.202016995.

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22

Li, Ke, Zhanqiang Xu, Han Deng, Zhennan Zhou, Yanfeng Dang, and Zhe Sun. "Dimeric Cycloparaphenylenes with a Rigid Aromatic Linker." Angewandte Chemie 133, no. 14 (February 26, 2021): 7727–31. http://dx.doi.org/10.1002/ange.202016995.

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23

Hashimoto, Sigma, Eiichi Kayahara, Yoshiyuki Mizuhata, Norihiro Tokitoh, Katsuhiko Takeuchi, Fumiyuki Ozawa, and Shigeru Yamago. "Synthesis and Physical Properties of Polyfluorinated Cycloparaphenylenes." Organic Letters 20, no. 18 (September 13, 2018): 5973–76. http://dx.doi.org/10.1021/acs.orglett.8b02715.

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24

Sibbel, Friederike, Katsuma Matsui, Yasutomo Segawa, Armido Studer, and Kenichiro Itami. "Selective synthesis of [7]- and [8]cycloparaphenylenes." Chem. Commun. 50, no. 8 (2014): 954–56. http://dx.doi.org/10.1039/c3cc48683d.

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25

Schaub, Tobias A., Johannes T. Margraf, Lev Zakharov, Karsten Reuter, and Ramesh Jasti. "Strain-Promoted Reactivity of Alkyne-Containing Cycloparaphenylenes." Angewandte Chemie 130, no. 50 (November 14, 2018): 16586–91. http://dx.doi.org/10.1002/ange.201808611.

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26

Schaub, Tobias A., Johannes T. Margraf, Lev Zakharov, Karsten Reuter, and Ramesh Jasti. "Strain-Promoted Reactivity of Alkyne-Containing Cycloparaphenylenes." Angewandte Chemie International Edition 57, no. 50 (November 14, 2018): 16348–53. http://dx.doi.org/10.1002/anie.201808611.

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27

Nogami, Juntaro, Yuki Nagashima, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama, and Ken Tanaka. "Asymmetric synthesis, structures, and chiroptical properties of helical cycloparaphenylenes." Chemical Science 12, no. 22 (2021): 7858–65. http://dx.doi.org/10.1039/d1sc00861g.

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The perfectly diastereo- and enantiocontrolled catalytic synthesis of a cycloparaphenylene with four helical and two planar chiralities showing good chiroptical responses was achieved by the rhodium-catalyzed alkyne cyclotrimerization.

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28

Bachrach, Steven M., and David Stück. "DFT Study of Cycloparaphenylenes and Heteroatom-Substituted Nanohoops." Journal of Organic Chemistry 75, no. 19 (October 2010): 6595–604. http://dx.doi.org/10.1021/jo101371m.

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29

Peña-Alvarez, Miriam, Lili Qiu, Valentín G. Baonza, Mercedes Taravillo, Miklos Kertesz, and Juan Casado. "Molecules under Pressure: The Case of [n]Cycloparaphenylenes." Chemistry of Materials 31, no. 17 (November 16, 2018): 6443–52. http://dx.doi.org/10.1021/acs.chemmater.8b04173.

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30

Zhao, Hongyan, Ying-Chao Ma, Lei Cao, Shiqing Huang, Jian-Ping Zhang, and Xiaoyu Yan. "Synthesis and Photophysical Properties of Chalcophenes-Embedded Cycloparaphenylenes." Journal of Organic Chemistry 84, no. 9 (March 28, 2019): 5230–35. http://dx.doi.org/10.1021/acs.joc.9b00207.

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31

Hu, Lizhi, Yandong Guo, Xiaohong Yan, Hongli Zeng, and Jie Zhou. "Electronic transport properties in [n]cycloparaphenylenes molecular devices." Physics Letters A 381, no. 25-26 (July 2017): 2107–11. http://dx.doi.org/10.1016/j.physleta.2017.04.035.

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32

Kayahara, Eiichi, Takahiro Iwamoto, Toshiyasu Suzuki, and Shigeru Yamago. "Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes." Chemistry Letters 42, no. 6 (June 5, 2013): 621–23. http://dx.doi.org/10.1246/cl.130188.

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33

Hashimoto, Sigma, Takahiro Iwamoto, Daisuke Kurachi, Eiichi Kayahara, and Shigeru Yamago. "Shortest Double-Walled Carbon Nanotubes Composed of Cycloparaphenylenes." ChemPlusChem 82, no. 7 (April 6, 2017): 1015–20. http://dx.doi.org/10.1002/cplu.201700097.

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34

Hashimoto, Sigma, Takahiro Iwamoto, Daisuke Kurachi, Eiichi Kayahara, and Shigeru Yamago. "Shortest Double-Walled Carbon Nanotubes Composed of Cycloparaphenylenes." ChemPlusChem 82, no. 7 (June 27, 2017): 942. http://dx.doi.org/10.1002/cplu.201700263.

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35

Iwamoto, Takahiro, Yoshiki Watanabe, Hikaru Takaya, Takeharu Haino, Nobuhiro Yasuda, and Shigeru Yamago. "Size- and Orientation-Selective Encapsulation of C70by Cycloparaphenylenes." Chemistry - A European Journal 19, no. 42 (September 17, 2013): 14061–68. http://dx.doi.org/10.1002/chem.201302694.

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36

Tran-Van, Anne-Florence, and Hermann A. Wegner. "Nano-rings with a handle – Synthesis of substituted cycloparaphenylenes." Beilstein Journal of Nanotechnology 5 (August 20, 2014): 1320–33. http://dx.doi.org/10.3762/bjnano.5.145.

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The research of cycloparaphenylenes (CPPs), the smallest armchair carbon nanotube, has been a quest for the past decades which experienced a revival in 2008 when the first synthesis was achieved. Since then CPPs with various ring sizes have been realized. The incorporation of substituents and the synthesis of CPPs with building blocks different from phenyl rings bear challenges of their own. Such structures, however, are highly interesting, as they allow for an incorporation of CPPs as defined nano-objects for other applications. Therefore, this review provides a status report about the current efforts in synthesizing CPPs beyond the parent unsubstituted oligo-phenylene structure.

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37

Kakarlamudi, Akhil Chakravarthy, and Sivaranjana Reddy Vennapusa. "Intersystem crossing pathways in [5]-, [7]-, and [9]cycloparaphenylenes." Journal of Chemical Physics 155, no. 4 (July 28, 2021): 044301. http://dx.doi.org/10.1063/5.0056605.

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38

Taubert, Stefan, Dage Sundholm, and Fabio Pichierri. "Magnetically Induced Currents in [n]Cycloparaphenylenes,n= 6−11." Journal of Organic Chemistry 75, no. 17 (September 3, 2010): 5867–74. http://dx.doi.org/10.1021/jo100902w.

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39

Ishii, Yuuki, Yusuke Nakanishi, Haruka Omachi, Sanae Matsuura, Katsuma Matsui, Hisanori Shinohara, Yasutomo Segawa, and Kenichiro Itami. "Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes." Chemical Science 3, no. 7 (2012): 2340. http://dx.doi.org/10.1039/c2sc20343j.

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40

Stojanović, Ljiljana, Saadullah G. Aziz, Rifaat H. Hilal, Felix Plasser, Thomas A. Niehaus, and Mario Barbatti. "Nonadiabatic Dynamics of Cycloparaphenylenes with TD-DFTB Surface Hopping." Journal of Chemical Theory and Computation 13, no. 12 (December 2017): 5846–60. http://dx.doi.org/10.1021/acs.jctc.7b01000.

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41

García-Rodeja, Yago, and Israel Fernández. "Factors Controlling the Reactivity of Strained-Alkyne Embedded Cycloparaphenylenes." Journal of Organic Chemistry 84, no. 7 (March 8, 2019): 4330–37. http://dx.doi.org/10.1021/acs.joc.9b00292.

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42

Fomine, Serguei, Mikhail G. Zolotukhin, and Patricia Guadarrama. "“Russian doll” complexes of [n]cycloparaphenylenes: a theoretical study." Journal of Molecular Modeling 18, no. 9 (March 30, 2012): 4025–32. http://dx.doi.org/10.1007/s00894-012-1402-7.

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43

Kanai, Kaname, Takuya Inoue, Takaya Furuichi, Kaito Shinoda, Takashi Iwahashi, and Yukio Ouchi. "Electronic structure of n-cycloparaphenylenes directly observed by photoemission spectroscopy." Physical Chemistry Chemical Physics 23, no. 14 (2021): 8361–67. http://dx.doi.org/10.1039/d1cp00625h.

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44

Maust, Ruth L., Penghao Li, Baihao Shao, Sarah M. Zeitler, Peiguan B. Sun, Harrison W. Reid, Lev N. Zakharov, Matthew R. Golder, and Ramesh Jasti. "Controlled Polymerization of Norbornene Cycloparaphenylenes Expands Carbon Nanomaterials Design Space." ACS Central Science 7, no. 6 (May 13, 2021): 1056–65. http://dx.doi.org/10.1021/acscentsci.1c00345.

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45

Tran-Van, Anne-Florence, Elena Huxol, Jonathan M. Basler, Markus Neuburger, Jean-Joseph Adjizian, Chris P. Ewels, and Hermann A. Wegner. "Synthesis of Substituted [8]Cycloparaphenylenes by [2 + 2 + 2] Cycloaddition." Organic Letters 16, no. 6 (March 5, 2014): 1594–97. http://dx.doi.org/10.1021/ol500194s.

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46

Jiang, Hua-Wei, Takayuki Tanaka, Hirotaka Mori, Kyu Hyung Park, Dongho Kim, and Atsuhiro Osuka. "Cyclic 2,12-Porphyrinylene Nanorings as a Porphyrin Analogue of Cycloparaphenylenes." Journal of the American Chemical Society 137, no. 6 (February 4, 2015): 2219–22. http://dx.doi.org/10.1021/ja513102m.

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47

Camacho, Cristopher, Thomas A. Niehaus, Kenichiro Itami, and Stephan Irle. "Origin of the size-dependent fluorescence blueshift in [n]cycloparaphenylenes." Chem. Sci. 4, no. 1 (2013): 187–95. http://dx.doi.org/10.1039/c2sc20878d.

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48

Segawa, Yasutomo, Haruka Omachi, and Kenichiro Itami. "Theoretical Studies on the Structures and Strain Energies of Cycloparaphenylenes." Organic Letters 12, no. 10 (May 21, 2010): 2262–65. http://dx.doi.org/10.1021/ol1006168.

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49

Nishigaki, Shuhei, Miho Fukui, Haruki Sugiyama, Hidehiro Uekusa, Susumu Kawauchi, Yu Shibata, and Ken Tanaka. "Synthesis, Structures, and Photophysical Properties of Alternating Donor–Acceptor Cycloparaphenylenes." Chemistry – A European Journal 23, no. 30 (May 2, 2017): 7227–31. http://dx.doi.org/10.1002/chem.201701547.

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50

Wu, Di, Wei Cheng, Xiangtao Ban, and Jianlong Xia. "Cycloparaphenylenes (CPPs): An Overview of Synthesis, Properties, and Potential Applications." Asian Journal of Organic Chemistry 7, no. 11 (October 8, 2018): 2161–81. http://dx.doi.org/10.1002/ajoc.201800397.

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