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Articles

Synthesis of a new C60 cyanofullerene derivative

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Pages 695-704 | Received 24 Mar 2023, Accepted 02 Apr 2023, Published online: 12 Apr 2023

References

  • Sita, M. L.; Changala, P. B.; Xue, C.; Burkhardt, A. M.; Shingledecker, C. N.; Lee, K. L. K.; Loomis, R. A.; Momjian, E.; Siebert, M. A.; Gupta, D.; et al. Discovery of Interstellar 2-Cyanoindene (2-C9H7CN) in GOTHAM Observations of TMC-1. ApJL 2022, 938, L12. DOI: 10.3847/2041-8213/ac92f4.
  • McCarthy, M. C.; Lee, K. L. K.; Loomis, R. A.; Burkhardt, A. M.; Shingledecker, C. N.; Charnley, S. B.; Cordiner, M. A.; Herbst, E.; Kalenskii, S.; Willis, E. R.; et al. Interstellar Detection of the Highly Polar Five-Membered Ring Cyanocyclopentadiene. Nat. Astron. 2020, 5, 176–180. DOI: 10.1038/s41550-020-01213-y.
  • Lee, K. L. K.; Changala, P. B.; Loomis, R. A.; Burkhardt, A. M.; Xue, C.; Cordiner, M. A.; Charnley, S. B.; McCarthy, M. C.; McGuire, B. A. Interstellar Detection of 2-Cyanocyclopentadiene, C5H5CN, a Second Five-Membered Ring toward TMC-1. ApJL 2021, 910, L2. DOI: 10.3847/2041-8213/abe764.
  • Burkhardt, A. M.; Loomis, R. A.; Shingledecker, C. N.; Lee, K. L. K.; Remijan, A. J.; McCarthy, M. C.; McGuire, B. A. Ubiquitous Aromatic Carbon Chemistry at the Earliest Stages of Star Formation. Nat. Astron. 2021, 5, 181–187. DOI: 10.1038/s41550-020-01253-4.
  • McGuire, B. A.; Loomis, R. A.; Burkhardt, A. M.; Lee, K. L. K.; Shingledecker, C. N.; Charnley, S. B.; Cooke, I. R.; Cordiner, M. A.; Herbst, E.; Kalenskii, S.; et al. Detection of Two Interstellar Polycyclic Aromatic Hydrocarbons via Spectral Matched Filtering. Science 2021, 371, 1265–1269. DOI: 10.1126/science.abb7535.
  • McGuire, B. A.; Burkhardt, A. M.; Loomis, R. A.; Shingledecker, C. N.; Kelvin Lee, K. L.; Charnley, S. B.; Cordiner, M. A.; Herbst, E.; Kalenskii, S.; Momjian, E.; et al. Early Science from GOTHAM: project Overview, Methods, and the Detection of Interstellar Propargyl Cyanide (HC≡C-CH2-CN) in TMC-1. ApJ 2020, 900, L10. DOI: 10.3847/2041-8213/aba632.
  • Lee, J.; Shin, J.; Snaith, O. N.; Kim, Y.; Few, C. G.; Devriendt, J.; Dubois, Y.; Cox, L. M.; Hong, S. E.; Kwon, O.-K.; et al. Discovery of Interstellar Trans-Cyanovinylacetylene (HC≡C-CH = CH-CN) and Vinylcyanoacetylene (H2C = CH-C≡C-CN) in GOTHAM Observations of TMC-1. ApJ 2021, 908, 11. DOI: 10.3847/2041-8213/abdbb9.
  • Loomis, R. A.; Burkhardt, A. M.; Shingledecker, C. N.; Charnley, S. B.; Cordiner, M. A.; Herbst, E.; Kalenskii, S.; Lee, K. L. K.; Willis, E. R.; Xue, C.; et al. An Investigation of Spectral Line Stacking Techniques and Application to the Detection of HC11N. Nat. Astron. 2021, 5, 188–196. DOI: 10.1038/s41550-020-01261-4.
  • Xue, C.; Willis, E. R.; Loomis, R. A.; Kelvin Lee, K. L.; Burkhardt, A. M.; Shingledecker, C. N.; Charnley, S. B.; Cordiner, M. A.; Kalenskii, S.; McCarthy, M. C.; et al. Detection of Interstellar H-C≡C-C≡C-NC and an Investigation of Isocyanopolyyne Chemistry under TMC-1 Conditions. ApJ 2020, 900, L9. DOI: 10.3847/2041-8213/aba631.
  • Remijan, A.; Scolati, H. N.; Burkhardt, A. M.; Changala, P. B.; Charnley, S. B.; Cooke, I. R.; et al. Astronomical detection of the interstellar anion C10H- toward TMC-1 from the GOTHAM large program on the GBT. arXiv preprint arXiv:2301.07760, 2023. DOI: 10.48550/arXiv.2301.07760.
  • Cernicharo, J.; Marcelino, N.; Pardo, J. R.; Agúndez, M.; Tercero, B.; de Vicente, P.; Cabezas, C.; Bermúdez, C. Interstellar Nitrile Anions: Detection of C3N− and C5N − in TMC-1. A&A 2020, 641, L9. DOI: 10.1051/0004-6361/202039231.
  • Balucani, N.; Asvany, O.; Huang, L. C. L.; Lee, Y. T.; Kaiser, R. I.; Osamura, Y.; Bettinger, H. F. Formation of Nitriles in the Interstellar Medium via Reactions of Cyano Radicals, CN (X 2Σ+), with Unsaturated Hydrocarbons. ApJ 2000, 545, 892–906. DOI: 10.1086/317848.
  • (a) Cataldo, F. Cyanopolyynes: carbon Chains Formation in a Carbon Arc Mimicking the Formation of Carbon Chains in the Circumstellar Medium. Internat. J. Astrobiol., 2004, 3, 237–246. (b) Cataldo, F. Polyynes and Cyanopolyynes Synthesis from the Submerged Electric Arc: About the Role Played by the Electrodes and Solvents in Polyynes Formation. Tetrahedron, 2004, 60, 4265–4274. 10.1016/j.tet.2004.03.033 (c) Cataldo, F. Polyynes: A New Class of Carbon Allotropes. About the Formation of Dicyanopolyynes from an Electric Arc between Graphite Electrodes in Liquid Nitrogen. Polyhedron, 2004, 23, 1889–1896. 10.1016/j.poly.2004.04.024 (d) Cataldo, F. Polyynes and Cyanopolyynes: their Synthesis with the Carbon Arc Gives the Same Abundances Occurring in Carbon-Rich Stars. Origins of Life Evolut. Biosph., 2006, 36, 467–475. 10.1007/s11084-006-9051-4 (e) Cataldo, F.; Ursini, O.; Angelini, G. Kinetics of Polyynes Formation with the Submerged Carbon Arc. J. Electroanal. Chem., 2007, 602, 82–90. 10.1016/j.jelechem.2006.12.005 DOI: 10.1017/S1473550404002149.
  • (a) García-Hernández, D. A.; Villaver, E.; García-Lario, P.; Acosta-Pulido, J. A.; Manchado, A.; Stanghellini, L.; Shaw, R. A.; Cataldo, F. Infrared study of fullerene planetary nebulae. ApJ 2012, 760, 107.; (b) Tielens, A. G. G. M. The molecular universe. Rev. Modern Phys., 2013, 85, 1021–1081 10.1103/RevModPhys.85.1021. DOI: 10.1088/0004-637X/760/2/107.
  • (a) Sheka, E. F. Computational synthesis of C60 cyano-and azopolyderivatives. J. Mol. Model. 2012, 18, 1409–1420.; (b) Sheka, E. F. Fullerenes: Nanochemistry, Nanomagnetism, Nanomedicine, Nanophotonics; CRC Press: Boca Raton, FL. DOI: 10.1007/s00894-011-1158-5.
  • Sabirov, D. S.; Garipova, R. R.; Cataldo, F. Polarizability of Isomeric and Related Interstellar Compounds in the Aspect of Their Abundance. Molecular Astrophys. 2018, 12, 10–19. DOI: 10.1016/j.molap.2018.05.001.
  • Keshavarz-K, M.; Knight, B.; Srdanov, G.; Wudl, F. Cyanodihydrofullerenes and Dicyanodihydrofullerene: The First Polar Solid Based on C60. J. Am. Chem. Soc. 1995, 117, 11371–11372. DOI: 10.1021/ja00150a048.
  • Jousselme, B.; Sonmez, G.; Wudl, F. Acidity and Electronegativity Enhancement of C60 Derivatives through Cyano Groups. J. Mater. Chem. 2006, 16, 3478–3482. DOI: 10.1039/b605668g.
  • (a) Khairallah, G.; Peel, J. B. Identification of Cyano Dianions of C60 by Electrospray Mass Spectrometry. Chem. Phys. Lett. 1997, 268, 218–222. (b) Khairallah, G.; Peel, J. B. Cyano Adduct Anions of C70: Electrospray Mass Spectrometric Studies. J. Phys. Chem. A, 1997, 101, 6770–6774. 10.1021/jp970635t (c) Khairallah, G.; Peel, J. B. Cyano Adduct Anions of Higher Fullerenes: electrospray Mass Spectrometric Studies. Int. J. Mass Spectrom. 2000, 194, 115–120. 10.1016/S1387-3806(99)00122-0 DOI: 10.1016/S0009-2614(97)00190-5.
  • Tuinman, A. A.; Compton, R. N. Structures of Gas-Phase (C60)n(CN)m Trianions from Reactions of C60 with NaCN in Solution. J. Phys. Chem. A 1998, 102, 9791–9796. DOI: 10.1021/jp983212f.
  • Komatsu, K.; Wang, G. W.; Murata, Y.; Tanaka, T.; Fujiwara, K.; Yamamoto, K.; Saunders, M. Mechanochemical Synthesis and Characterization of the Fullerene Dimer C120. J. Org. Chem 1998, 63, 9358–9366. DOI: 10.1021/jo981319t.
  • Troshin, P. A.; Khakina, E. A.; Peregudov, A. S.; Konarev, D. V.; Soulimenkov, I. V.; Peregudova, S. M.; Lyubovskaya, R. N. [C60(CN)5]–: A Remarkably Stable [60]Fullerene Anion. Eur. J. Org. Chem 2010, 2010, 3265–3268. DOI: 10.1002/ejoc.201000016.
  • Taylor, R. Lecture Notes on Fullerene Chemistry: A Handbook for Chemists. Imperial College Press/World Scientific: Singapore, 1999.
  • Cataldo, F.; Garcia-Hernandez, D. A.; Manchado, A. Thermochemical Properties of C60Br24. Fullerenes, Nanotub. Carbon Nanostruct 2023. DOI: 10.1080/1536383X.2023.2187049.
  • (a) Semenov, K. N.; Charykov, N. A.; Keskinov, V. A.; Pyartman, A. K.; Yakovlev, V. V.; Arapov, O. V. The Solubility of C60Brn (n= 6, 8, 24) in Organic Solvents.Russ. J. Phys. Chem., 2009, 83, 1935–1939. (b) Semenov, K. N.; Charykov, N. A.; Axel’rod, B. M. Solubility of Bromoderivatives C60Brn (n= 6, 8, 24) in 1-Chloronaphthalene and 1-Bromonaphthalene in the Temperature Range 10° to 60 °C. J. Chem. Eng. Data, 2010, 55, 3662–3666. 10.1021/je100224a DOI: 10.1134/S003602440911020X.
  • Papina, T. S.; Luk’yanova, V. A.; Troyanov, S. I.; Burtsev, A. V.; Serov, M. G.; Ioutsi, V. A.; Buyanovskaya, A. G.; Levinskaya, O. A. Standard Enthalpy of Formation of Fullerene Bromide C60Br24. Moscow Univ. Chem. Bull. 2013, 68, 12–16. DOI: 10.3103/S0027131413010124.
  • Dean, J. A. Lange’s Handbook of Chemistry 15th ed. McGraw-Hill: New York, 1999.
  • (a) Łubkowski, J.; Błażejowski, J. Thermal Properties and Thermochemistry of Alkanaminium Bromides. Thermochim. Acta, 1990, 157: 259–277. (b) Mitra, S.; Singh, H. P. The Thermal Investigation of Some Normal Propylammonium Salts in the Solid State. Thermochim. Acta, 1993, 225, 43–51. 10.1016/0040-6031(93)85081-J (c) Prasad, M. R. R.; Krishnamurthy, V. N. Thermal Decomposition and pyrolysis-GC Studies on Tetraalkyl-Substituted Ammonium Hexafluorophosphates. Thermochim. Acta, 1991, 185, 1–10. 10.1016/0040-6031(91)80112-V (d) Prasad, M. R. R.; Krishnan, K.; Ninan, K. N.; Krishnamurthy, V. N. Thermal Decomposition of Tetraalkyl Ammonium Tetrafluoroborates. Thermochim. Acta, 1997, 297, 207–210. 10.1016/S0040-6031(96)03070-5 (e) Błazejowsk, J.; Kowalewska, E. Thermal Decomposition of Alkylammonium Chlorides. Thermochim. Acta, 1985, 92, 811–814. 10.1016/0040-6031(85)86001-9 (f) Błażejowski, J.; Kowalewska, E. Thermal Properties of Amine Hydrochlorides: Part II. Thermolysis and Thermochemistry of Alkanaminium Chlorides. Thermochim. Acta, 1986, 105, 257–286. 10.1016/0040-6031(86)85244-3 (g) Dokurno, P.; Łubkowski, J.; Błȧejowski, J. Thermal Properties, Thermolysis and Thermochemistry of Alkanaminium Iodides. Thermochim. Acta, 1990, 165, 31–48. 10.1016/0040-6031(90)80204-C DOI: 10.1016/0040-6031(90)80027-V.
  • Nuevo, M.; Milam, S. N.; Sandford, S. A.; De Gregorio, B. T.; Cody, G. D.; Kilcoyne, A. L. D. XANES Analysis of Organic Residues Produced from the UV Irradiation of Astrophysical Ice Analogs. Adv. Space Res. 2011, 48, 1126–1135. DOI: 10.1016/j.asr.2011.05.020.
  • Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules. Academic Press: San Diego, 1991.

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