Carbon nanohoop

Carbon nanohoops are a class of molecules consisting of aromatic sections curved out of planarity by the inherent cyclic geometry of the molecule. This class of molecules came into existence with the synthesis of cycloparaphenylenes[1] by Ramesh Jasti in the lab of Carolyn Bertozzi and since then has been expanded into cyclonaphthylenes,[2] cyclochrysenylenes,[3] and even cyclohexabenzocoronenylenes.[4] Moreover, several nanohoops containing such antiaromatic units as dibenzo[a,e]pentalene[5] and pyrrolo[3,2-b]pyrrole are reported.[6] Carbon nanohoops often map on to a certain chirality of carbon nanotube.[7][8] If the diameter is adequate, these molecules can host a fullerene. For example, [10]cycloparaphenylene can host a C60 fullerene.

The first carbon nanohoop was entirely made of phenylenes. Newer examples contain other aromatic repeating units.

References
  1. Jasti, Ramesh; Bhattacharjee, Joydeep; Neaton, Jeffrey B.; Bertozzi, Carolyn R. (2008). "Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures". Journal of the American Chemical Society. 130 (52): 17646–17647. doi:10.1021/ja807126u. PMC 2709987. PMID 19055403.
  2. Okada, Keishu; Yagi, Akiko; Segawa, Yasutomo; Itami, Kenichiro (2017). "Synthesis and properties of [8]-, [10]-, [12]-, and [16]cyclo-1,4-naphthylenes". Chemical Science. 8 (1): 661–667. doi:10.1039/C6SC04048A. PMC 5297897. PMID 28451214.
  3. Sun, Zhe; Suenaga, Takuya; Sarkar, Parantap; Sato, Sota; Kotani, Motoko; Isobe, Hiroyuki (2016). "Stereoisomerism, crystal structures, and dynamics of belt-shaped cyclonaphthylenes" (PDF). Proceedings of the National Academy of Sciences. 113 (29): 8109–8114. Bibcode:2016PNAS..113.8109S. doi:10.1073/pnas.1606530113. PMC 4961134. PMID 27357686.
  4. Nakagawa, Yuta; Sekiguchi, Ryuta; Kawakami, Jun; Ito, Shunji (2019). "Preparation of a large-sized highly flexible carbon nanohoop". Organic & Biomolecular Chemistry. 17 (28): 6843–6853. doi:10.1039/C9OB00763F. PMID 31263811. S2CID 195771118.
  5. Wössner, Jan; Wassy, Daniel; Weber, Andrej; Bovenkerk, Marcel; Hermann, Mathias; Schmidt, Maximilian; Esser, Birgit (2021). "[n]Cyclodibenzopentalenes as Antiaromatic Curved Nanocarbons with High Strain and Strong Fullerene Binding". Journal of the American Chemical Society. 143 (31): 12244–12252. doi:10.1021/jacs.1c05251. PMID 34324813. S2CID 236516486.
  6. George, Gibu; Stasyuk, Olga; Voityuk, Alexander; Stasyuk, Anton; Solà, Miquel (2023). "Aromaticity controls the excited-state properties of host-guest complexes of nanohoops". Nanoscale. 15 (3): 1221–1229. doi:10.1039/D2NR04037A. PMID 36537223. S2CID 254673214.
  7. "Möbius Carbon Nanobelt: A Möbius Strip Constructed Solely of Carbon Atoms". 28 May 2022.
  8. Segawa, Yasutomo; Watanabe, Tsugunori; Yamanoue, Kotono; Kuwayama, Motonobu; Watanabe, Kosuke; Pirillo, Jenny; Hijikata, Yuh; Itami, Kenichiro (2022). "Synthesis of a Möbius carbon nanobelt". Nature Synthesis. 1 (7): 535–541. doi:10.1038/s44160-022-00075-8. S2CID 248928006.


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