Skip to content
2000
image of Sonochemical Reactions Involving Fullerenes C60 and C70

Abstract

The construction of exohedral adducts of C and C fullerenes containing acyclic and cyclic addends using ultrasound is unconventional in the chemistry of cage compounds. In this regard, ultrasound can be a universal tool in framework chemistry. The use of ultrasound reduces reaction times for fullerenes C and C, increases product yields, and serves as a convenient tool for targeted modification of chemical bonds, allowing the transformation of more accessible precursors into less accessible compounds. In heterogeneous reactions, ultrasound eliminates the need for phase transfer catalysts. This review presents the theoretical foundations of sonochemistry, sonochemical methods for obtaining inorganic and organic derivatives of fullerenes C and C, including [n+2]-cycloaddition reactions (n=1,3,4) and reactions of formation of fullerene adducts with acyclic fragments, as well as reactions of structural isomerization of [5,6]-open to [6,6]-closed isomers containing norbornane and adamantane fragments.

Loading

Article metrics loading...

/content/journals/coc/10.2174/0113852728425497251201060521
2026-01-02
2026-02-27
Loading full text...

Full text loading...

References

  1. Piotrovsky L.B. Kisilev O.I. Fullerenes in biology. St. Petersburg OOO Rostok 2006
    [Google Scholar]
  2. Troshin P.A. Lyubovskaya R.N. Razumov V.F. Organic solar batteries: Structure, materials, critical parameters and development prospects. Russ Nanotechnol. 2008 3 6 27
    [Google Scholar]
  3. Fullagar W.K. Reynolds P.A. White J.W. Lithium and sodium fullerides prepared in liquid ammonia. Solid State Commun. 1997 104 1 23 27 10.1016/S0038‑1098(97)00229‑9
    [Google Scholar]
  4. Otsuka A. Saito G. Zakhidov A.A. Yakushi K. Superconductivity in charge transfer complexes of C60. Synth. Met. 1997 85 1-3 1459 1460 10.1016/S0379‑6779(97)80315‑3
    [Google Scholar]
  5. Li Y. Mao Z. Xu J. Yang J. Guo Z. Zhu D. Li J. Yin B. Preparation of a novel stable nitroxide based on [60]fulleropyrrolidine and its magnetic properties. Chem. Phys. Lett. 1997 265 3-5 361 364 10.1016/S0009‑2614(96)01454‑6
    [Google Scholar]
  6. Li Y.L. Xu J.H. Zheng D.G. Yang J.K. Pan C.Y. Zhu D.B. Synthesis and characterization of stable nitroxides based on fullerenes (C60, C70) and their magnetic study. Solid State Commun. 1997 101 2 123 128 10.1016/S0038‑1098(96)00502‑9
    [Google Scholar]
  7. Troshin P.A. Lyubovskaya R.N. Organic chemistry of fullerenes: the major reactions, types of fullerene derivatives and prospects for practical use. Russ. Chem. Rev. 2008 77 4 323 369 10.1070/RC2008v077n04ABEH003770
    [Google Scholar]
  8. Synthesis, Properties & Applications Verner R.F. Benvegnu C. Hauppauge Nova Science Pub Inc. 2012 548
    [Google Scholar]
  9. Nouraliei M. Javadian H. Mehdizadeh K. Sheibanian N. Douk A.S. Mohammadzadeh F. Osouleddini N. Fullerene carbon nanostructures for the delivery of phenelzine derivatives as new drugs to inhibit monoamine oxidase enzyme: Molecular docking interactions and density functional theory calculations. Colloids Surf. A Physicochem. Eng. Asp. 2023 657 130599 10.1016/j.colsurfa.2022.130599
    [Google Scholar]
  10. Al Garalleh H. Fullerene derivatives (CN-[OH]β) and single-walled carbon nanotubes modelled as transporters for doxorubicin drug in cancer therapy. Int. J. Mol. Sci. 2022 23 17 9646 10.3390/ijms23179646 36077042
    [Google Scholar]
  11. Kulkarni S. Chaudhari S.B. Chikkamath S.S. Kurale R.S. Thopate T.S. Praveenkumar S. Ghotekar S. Patil P. Kumar D. Potential applications of fullerenes in drug delivery and medical advances. Inorg. Chem. Commun. 2025 173 113829 10.1016/j.inoche.2024.113829
    [Google Scholar]
  12. Hou W. Shi G. Wu S. Mo J. Shen L. Zhang X. Zhu Y. Application of fullerenes as photosensitizers for antimicrobial photodynamic inactivation: A review. Front. Microbiol. 2022 13 957698 10.3389/fmicb.2022.957698 35910649
    [Google Scholar]
  13. He K. Ran H. Su Z. Wang Z. Li M. Hao L. Perfluorohexane-encapsulated fullerene nanospheres for dual-modality US/CT imaging and synergistic high-intensity focused ultrasound ablation. Int. J. Nanomedicine 2019 14 519 529 10.2147/IJN.S184579 30666111
    [Google Scholar]
  14. Sharoyko V.V. Shemchuk O.S. Meshcheriakov A.A. Vasina L.V. Iamalova N.R. Luttsev M.D. Ivanova D.A. Petrov A.V. Maystrenko D.N. Molchanov O.E. Semenov K.N. Biocompatibility, antioxidant activity and collagen photoprotection properties of C60 fullerene adduct with L-methionine. Nanomedicine 2022 40 102500 10.1016/j.nano.2021.102500 34843985
    [Google Scholar]
  15. Babuska V. Kasi P.B. Chocholata P. Wiesnerova L. Dvorakova J. Vrzakova R. Nekleionova A. Landsmann L. Kulda V. Nanomaterials in bone regeneration. Appl. Sci. 2022 12 13 6793 10.3390/app12136793
    [Google Scholar]
  16. Prato M. [60]Fullerene chemistry for materials science applications. J. Mater. Chem. 1997 7 7 1097 1109 10.1039/a700080d
    [Google Scholar]
  17. Yang X. Ebrahimi A. Li J. Cui Q. Fullerene-biomolecule conjugates and their biomedicinal applications. Int. J. Nanomedicine 2014 9 77 92 10.2147/IJN.S71700 24379667
    [Google Scholar]
  18. Mikheev I.V. Pirogova M.O. Usoltseva L.O. Uzhel A.S. Bolotnik T.A. Kareev I.E. Bubnov V.P. Lukonina N.S. Volkov D.S. Goryunkov A.A. Korobov M.V. Proskurnin M.A. Green and rapid preparation of long-term stable aqueous dispersions of fullerenes and endohedral fullerenes: The pros and cons of an ultrasonic probe. Ultrason. Sonochem. 2021 73 105533 10.1016/j.ultsonch.2021.105533 33799110
    [Google Scholar]
  19. Oh W.C. Meng Z.D. Ko W.B. Preparation of fullerene function materials under ultrasonic irradiation: Review. J. Photocatl. Sci. 2011 2 1 39 6
    [Google Scholar]
  20. Richards W.T. Loomis A.L. The chemical effects of high frequency sound waves I. A preliminary suvey. J. Am. Chem. Soc. 1927 49 12 3086 3100 10.1021/ja01411a015
    [Google Scholar]
  21. Schmitt F.O. Johnson C.H. Olson A.R. Oxidations promoted by ultrasonic radiation. J. Am. Chem. Soc. 1929 51 2 370 375 10.1021/ja01377a004
    [Google Scholar]
  22. Adewuyi Y.G. Sonochemistry: Environmental science and engineering applications. Ind. Eng. Chem. Res. 2001 40 22 4681 4715 10.1021/ie010096l
    [Google Scholar]
  23. Margulis M.A. Sonochemistry and cavitation. Langhorne Gordon and Breach Publishers 1995
    [Google Scholar]
  24. Margulis M.A. Fundamentals of sound chemistry (chemical reactions in sound fields). Moscow Higher School 1984
    [Google Scholar]
  25. Mason T.J. Lorimer J.P. Theory, Applications and Uses of Ultrasound. in Chemistry. Ellis Horwood Publishers 1988
    [Google Scholar]
  26. L K. Ultrasound. Its Chemical, Physical, and Biological Effects. Science Kenneth S. Suslick VCH, New York, 1988 xiv, 336 pp., illus. $65. Science 1989 243 4897 1499 1499 10.1126/science.243.4897.1499‑a 17839755
    [Google Scholar]
  27. Suslick K.S. Sonochemistry. Science 1990 247 4949 1439 1445 10.1126/science.247.4949.1439 17791211
    [Google Scholar]
  28. Suslick K.S. The chemical effects of ultrasound. Sci. Am. 1989 260 2 80 86 10.1038/scientificamerican0289‑80
    [Google Scholar]
  29. Henglein A. Sonochemistry: Historical developments and modern aspects. Ultrasonics 1987 25 1 6 16 10.1016/0041‑624X(87)90003‑5
    [Google Scholar]
  30. Suslick K.S. Doktycz S.J. Flint E.B. On the origin of sonoluminescence and sonochemistry. Ultrasonics 1990 28 5 280 290 10.1016/0041‑624X(90)90033‑K 2203195
    [Google Scholar]
  31. Negishi K. Experimental studies on sonoluminescence and ultrasonic cavitation. J. Phys. Soc. Jpn. 1961 16 7 1450 1465 10.1143/JPSJ.16.1450
    [Google Scholar]
  32. Yasui K. Tuziuti T. Sivakumar M. Iida Y. Sonoluminescence. Appl. Spectrosc. Rev. 2004 39 3 399 436 10.1081/ASR‑200030202
    [Google Scholar]
  33. Suslick K.S. Flint E.B. Sonoluminescence from non-aqueous liquids. Nature 1987 330 6148 553 555 10.1038/330553a0 3683572
    [Google Scholar]
  34. Crum L.A. Putterman S. Acoustics 1991. Sonoluminescence. J. Acoust. Soc. Am 1992 91 1 517 517 10.1121/1.402741
    [Google Scholar]
  35. Weissler A. Cooper H.W. Snyder S. Chemical effect of ultrasonic waves: Oxidation of Potassium Iodide solution by carbon tetrachloride. J. Am. Chem. Soc. 1950 72 4 1769 1775 10.1021/ja01160a102
    [Google Scholar]
  36. Zechmeister L. Wallcave L. On the cleavage of benzene, thiophene and furan rings by means of ultrasonic waves. J. Am. Chem. Soc. 1955 77 10 2853 2855 10.1021/ja01615a056
    [Google Scholar]
  37. Zechmeister L. Magoon E.F. On the ultrasonic cleavage of the pyridine ring. J. Am. Chem. Soc. 1956 78 10 2149 2150 10.1021/ja01591a031
    [Google Scholar]
  38. Currell D.L. Zechmeister L. On the ultrasonic cleavage of some aromatic and heterocyclic rings. J. Am. Chem. Soc. 1958 80 1 205 208 10.1021/ja01534a051
    [Google Scholar]
  39. Margulis M.A. Sound-chemical reactions and sonoluminescence. Moscow Chemistry 1986
    [Google Scholar]
  40. Noltingk B.E. Neppiras E.A. Cavitation produced by Ultrasonics. Proc. Phys. Soc. B 1950 63 9 674 685 10.1088/0370‑1301/63/9/305
    [Google Scholar]
  41. Neppiras E.A. Acoustic cavitation. Physics Reports 1980 61 3 159 10.1016/0370‑1573(80)90115‑5
    [Google Scholar]
  42. McNamara W.B. Didenko Y.T. Suslick K.S. Sonoluminescence temperatures during multi-bubble cavitation. Nature 1999 401 6755 772 775 10.1038/44536
    [Google Scholar]
  43. Spurlock L.A. Reifsneider S.B. Chemistry of ultrasound. I. Reconsideration of first principles and the applications to a dialkyl sulfide. J. Am. Chem. Soc. 1970 92 21 6112 6117 10.1021/ja00724a003
    [Google Scholar]
  44. Lorimer J.P. Mason T.J. Sonochemistry. Part 1—The physical aspects. Chem. Soc. Rev. 1987 16 0 239 274 10.1039/CS9871600239
    [Google Scholar]
  45. Rooze J. Rebrov E.V. Schouten J.C. Keurentjes J.T.F. Dissolved gas and ultrasonic cavitation – A review. Ultrason. Sonochem. 2013 20 1 1 11 10.1016/j.ultsonch.2012.04.013 22705074
    [Google Scholar]
  46. Flint E.B. Suslick K.S. The temperature of cavitation. Science 1991 253 5026 1397 1399 10.1126/science.253.5026.1397 17793480
    [Google Scholar]
  47. Sivakumar M. Senthilkumar P. Majumdar S. Pandit A.B. Ultrasound mediated alkaline hydrolysis of methyl benzoate – reinvestigation with crucial parameters. Ultrason. Sonochem. 2002 9 1 25 30 10.1016/S1350‑4177(01)00099‑2 11602992
    [Google Scholar]
  48. Manickam S. Arigela V.N.D. Gogate P.R. Intensification of synthesis of biodiesel from palm oil using multiple frequency ultrasonic flow cell. Fuel Process. Technol. 2014 128 388 393 10.1016/j.fuproc.2014.08.002
    [Google Scholar]
  49. Mišík V. Riesz P. Detection of primary free radical species in aqueous sonochemistry by EPR spectroscopy. Sonochemistry and Sonoluminescence. Dordrecht Springer Netherlands 1999 225 236 10.1007/978‑94‑015‑9215‑4_18
    [Google Scholar]
  50. Mandrus D. Kele M. Hettich R.L. Guiochon G. Sales B.C. Boatner L.A. Sonochemical synthesis of C60H2. J. Phys. Chem. B 1997 101 2 123 128 10.1021/jp962056e
    [Google Scholar]
  51. Sokolov V.I. Stankevich I.V. The fullerenes — new allotropic forms of carbon: Molecular and electronic structure, and chemical properties. Russ. Chem. Rev. 1993 62 5 419 435 10.1070/RC1993v062n05ABEH000025
    [Google Scholar]
  52. Karaulova E.N. Bagrii E.I. Fullerenes: Functionalisation and prospects for the use of derivatives. Russ. Chem. Rev. 1999 68 11 889 907 10.1070/RC1999v068n11ABEH000499
    [Google Scholar]
  53. Diederich F. Thilgen C. Covalent Fullerene Chemistry. Science 1996 271 5247 317 324 10.1126/science.271.5247.317
    [Google Scholar]
  54. Sokolov V.I. The problem of fullerenes. The chemical aspect. Russ. Chem. Bull. 1993 42 1 1 11 10.1007/BF00699966
    [Google Scholar]
  55. Lebedkin S. Ballenwega S. Gross J. Taylor R. Krätschmer W. Synthesis of C120O: A new dimeric [60]fullerene derivative. Tetrahedron Lett. 1995 36 28 4971 4974 10.1016/00404‑0399(50)0784A‑
    [Google Scholar]
  56. Giesa S. Gross J.H. Gleiter R. Giesa S. Gromov A. Krätschmer W. Hull W.E. Lebedkin S. C120OS: the first sulfur-containing dimeric [60]fullerene derivative. Chem. Commun. (Camb.) 1999 465–466 5 465 466 10.1039/a809831j
    [Google Scholar]
  57. Smith A.B. Tokuyama H. Strongin R.M. Furst G.T. Romanow W.J. Chait B.T. Mirza U.A. Haller I. Synthesis of oxo- and methylene-bridged C60 dimers, the first well-characterized species containing fullerene-fullerene bonds. J. Am. Chem. Soc. 1995 117 36 9359 9360 10.1021/ja00141a031
    [Google Scholar]
  58. Fedurco M. Costa D.A. Balch A.L. Fawcett W.R. Electrochemical Synthesis of a Redox‐Active Polymer Based on Buckminsterfullerene Epoxide. Angew. Chem. Int. Ed. Engl. 1995 34 2 194 196 10.1002/anie.199501941
    [Google Scholar]
  59. Ko W.B. Baek K.N. The oxidation of fullerene [C70] with various oxidants by ultrasonication. Ultrasonics 2002 39 10 729 733 10.1016/S0041‑624X(02)00377‑3 12479604
    [Google Scholar]
  60. Ko W.B. Nam J.H. Hwang S.H. The oxidation of fullerene[C60] with various amine N-oxides under ultrasonic irradiation. Ultrasonics 2004 42 1-9 611 615 10.1016/j.ultras.2004.01.083 15047355
    [Google Scholar]
  61. Cataldo F. Ursini O. Ragni P. Ultrasound-assisted Bromination. Part 1: Bromination of C60 and C70. Fuller. Nanotub. Carbon Nanostruct. 2013 21 4 346 356 10.1080/1536383X.2011.613544
    [Google Scholar]
  62. Ko W.B. Park Y.H. Jeong M.K. Preparation of a water-soluble fullerene [C70] under ultrasonic irradiation. Ultrasonics 2006 44 e367 e369 (Suppl. 1) 10.1016/j.ultras.2006.05.004 16814829
    [Google Scholar]
  63. Ko W.B. Heo J.Y. Nam J.H. Lee K.B. Synthesis of a water-soluble fullerene [C60] under ultrasonication. Ultrasonics 2004 41 9 727 730 10.1016/j.ultras.2003.12.029 14996532
    [Google Scholar]
  64. Afreen S. Kokubo K. Muthoosamy K. Manickam S. Hydration or hydroxylation: direct synthesis of fullerenol from pristine fullerene [C60] via acoustic cavitation in the presence of hydrogen peroxide. RSC Advances 2017 7 51 31930 31939 10.1039/C7RA03799F
    [Google Scholar]
  65. Labille J. Masion A. Ziarelli F. Rose J. Brant J. Villiéras F. Pelletier M. Borschneck D. Wiesner M.R. Bottero J.Y. Hydration and dispersion of C60 in aqueous systems: the nature of water-fullerene interactions. Langmuir 2009 25 19 11232 11235 10.1021/la9022807 19725560
    [Google Scholar]
  66. Cataldo F. Ursini O. Ragni P. Fullerene C60 trichloromethylation through CCl4 plasmalysis or sonolysis. Plasma Chem. Plasma Process. 2013 33 1 355 365 10.1007/s11090‑012‑9417‑5
    [Google Scholar]
  67. Kaushik P. Kaushik G. An assessment of structure and toxicity correlation in organochlorine pesticides. J. Hazard. Mater. 2007 143 1-2 102 111 10.1016/j.jhazmat.2006.08.073 17011119
    [Google Scholar]
  68. Long K. Boyce M. Lin H. Yuan J. Ma D. Structure–activity relationship studies of salubrinal lead to its active biotinylated derivative. Bioorg. Med. Chem. Lett. 2005 15 17 3849 3852 10.1016/j.bmcl.2005.05.120 16002288
    [Google Scholar]
  69. McCarty G.W. Modes of action of nitrification inhibitors. Biol. Fertil. Soils 1999 29 1 1 9 10.1007/s003740050518
    [Google Scholar]
  70. Gao X. Ishimura K. Nagase S. Chen Z. Dichlorocarbene addition to C60 from the trichloromethyl anion: carbene mechanism or Bingel mechanism? J. Phys. Chem. A 2009 113 15 3673 3676 10.1021/jp900265g 19317394
    [Google Scholar]
  71. Yinghuai Z. Bahnmueller S. Chibun C. Carpenter K. Hosmane N.S. Maguire J.A. An effective system to synthesize methanofullerenes: substrate–ionic liquid–ultrasonic irradiation. Tetrahedron Lett. 2003 44 29 5473 5476 10.1016/S0040‑4039(03)01299‑1
    [Google Scholar]
  72. Yinghuai Z. Application of ultrasound technique in the synthesis of methanofullerene derivatives. J. Phys. Chem. Solids 2004 65 2-3 349 353 10.1016/j.jpcs.2003.08.027
    [Google Scholar]
  73. Yoon S. Hwang S.H. Ko W.B. Cycloaddition of 2′-azidoethyl glycosides to fullerene[C60] under ultrasonic irradiation. Curr. Appl. Phys. 2008 8 6 774 777 10.1016/j.cap.2007.04.022
    [Google Scholar]
  74. Yoon S. Ho Hwang S. Bae Ko W. Sonochemical reaction of fullerene[C60] with several 2′-azidoethyl per-O-acetyl glycosides. J. Nanosci. Nanotechnol. 2008 8 6 3136 3141 10.1166/jnn.2008.091 18681058
    [Google Scholar]
  75. Yoon S. Hwang S.H. Ko W.B. Ultrasound-assisted cycloadditions of [70]fullerene with various 2-azidoethyl per-O-acetyl glycosides. Fuller. Nanotub. Carbon Nanostruct. 2009 17 5 496 506 10.1080/15363830903130051
    [Google Scholar]
  76. Yoon S.S. Hwang S.H. Hong S.K. Lee J.H. Ko W.B. Sonochemical synthesis of closed [5,6]-bridged Aziridino[70]fullerene derivative and selfassembled multilayer films. Carbon letters 2009 10 4 325 328 10.5714/CL.2009.10.4.325
    [Google Scholar]
  77. Zhang X. Gan L. Huang S. Shi Y. Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C60) and amino acid esters. J. Org. Chem. 2004 69 17 5800 5802 10.1021/jo0493368 15307764
    [Google Scholar]
  78. Zhdankin V.V. Stang P.J. Recent developments in the chemistry of polyvalent iodine compounds. Chem. Rev. 2002 102 7 2523 2584 10.1021/cr010003+ 12105935
    [Google Scholar]
  79. Safaei-Ghomi J. Masoomi R. An efficient comparison of methods involving conventional, grinding and ultrasound conditions for the synthesis of fulleroisoxazolines. Ultrason. Sonochem. 2015 23 212 218 10.1016/j.ultsonch.2014.08.004 25224855
    [Google Scholar]
  80. Cataldo F. García-Hernández D.A. Manchado A. Sonochemical synthesis of fullerene C60/Anthracene diels-alder mono and bis-adducts. Fuller. Nanotub. Carbon Nanostruct. 2014 22 6 565 574 10.1080/1536383X.2012.702160
    [Google Scholar]
  81. Kinzyabaeva Z.S. Sharipov G.L. A selective synthesis of the fullerene-fused dioxane adduct via heterogeneous reaction of C60 with α-diols and NaOH under ultrasonication. Ultrason. Sonochem. 2018 42 119 123 10.1016/j.ultsonch.2017.11.012 29429652
    [Google Scholar]
  82. Kinzyabaeva Z.S. Sharipov G.L. Sonochemical synthesis of 5,6-Dihydro[C70-D5h(6)][5,6](1,4-dioxano)fullerene by reaction of fullerene with α-Diols. Russ. J. Org. Chem. 2018 54 7 1112 1115 10.1134/S1070428018070254
    [Google Scholar]
  83. McDonell W.R. Newton A.S. The radiation chemistry of the aliphatic alcohols 1,2. J. Am. Chem. Soc. 1954 76 18 4651 4658 10.1021/ja01647a051
    [Google Scholar]
  84. Kinzyabaeva Z.S. Sadykov R.A. Sharipov G.L. Free-radical mechanism of the sonochemical reaction of fullerenes C60 and C70 with ethylene glycol in the presence of NaOH. Fuller. Nanotub. Carbon Nanostruct. 2019 27 11 878 886 10.1080/1536383X.2019.1653857
    [Google Scholar]
  85. Kinzyabaeva Z.S. Sharipov G.L. Synthesis of dioxane derivative C70 in heterogeneous reaction of fullerene with ethylene glycol under the action of ultrasound. Bull. Ufa. Scien. Cen. RAS 2017 4 46 50
    [Google Scholar]
  86. Kinzyabaeva Z.S. Sabirov D.S. Sonochemical synthesis of novel C60 fullerene 1,4-oxathiane derivative through the intermediate fullerene radical anion. Ultrason. Sonochem. 2020 67 105169 10.1016/j.ultsonch.2020.105169 32417624
    [Google Scholar]
  87. Subramanian R. Boulas P. Vijayashree M.N. D’Souza F. Jones M.T. Kadish K.M. A facile and selective method for the solution-phase generation of C60- and C602-. J. Chem. Soc. Chem. Commun. 1994 16 16 1847 1848 10.1039/c39940001847
    [Google Scholar]
  88. Wu M. Wei X. Qi L. Xu Z. Xu Z. A new method for facile and selective generation of C60− and C602− in aqueous caustic/THF(or DMSO). Tetrahedron Lett. 1996 37 41 7409 7412 10.1016/0040‑4039(96)01613‑9
    [Google Scholar]
  89. Kinzyabaeva Z.S. Method for obtaining 1,9-(1',4'-Oxathiano-4'-oxide)-1,9-Dihydro-(C60-Ih)[5,6]Fullerene. Ru Patent 2785692 2022
  90. Kinzyabaeva Z.S. Ultrasound-assisted synthesis of C60 fullerene-fused 1,4-oxathian-2-ones. Russ. J. Gen. Chem. 2023 93 S1 S131 S136 10.1134/S1070363223140219
    [Google Scholar]
  91. Rabinovich V.A. Khavin Z.Ya. Brief Chemical Handbook. Leningrad Chemistry 1991
    [Google Scholar]
  92. Kinzyabaeva Z.S. Sharipov G.L. Sabirov D.S. The first steps toward C70 cycloadducts with a sulfur–fullerene bond: A selective sonochemical synthesis of single C70–1,4-oxathiane. Fuller. Nanotub. Carbon Nanostruct. 2021 29 2 137 143 10.1080/1536383X.2020.1816975
    [Google Scholar]
  93. Kinzyabaeva Z.S. Fazletdinova Z.N. C C60-Fulleromorpholine: Sonochemical synthesis and antiradical activity. Bulletin of Bashkir Univ 2022 10.33184/bulletin‑bsu‑2022.4.20
    [Google Scholar]
  94. Kinzyabaeva Z.S. Sabirov D.S. New sonochemical reactions of the C60 fullerene with amino alcohols yielding morpholine–C60 adducts. Fuller. Nanotub. Carbon Nanostruct. 2022 30 11 1134 1141 10.1080/1536383X.2022.2078314
    [Google Scholar]
  95. Kinzyabaeva Z.S. Sabirov D.Sh. Synthesis of hybrid molecules of fullerene C60 with catecholamines under the action of ultrasound. Russ. J. Org. Chem. 2023 59 237 242 10.31857/S051474922302009X
    [Google Scholar]
  96. Lobach A.S. Goldshleger N.F. Kaplunov M.G. Kulikov A.V. Near-IR and ESR studies of the radical anions of C60 and C70 in the system fullerene-primary amine. Chem. Phys. Lett. 1995 243 1-2 22 28 10.1016/0009‑2614(95)00811‑H
    [Google Scholar]
  97. Hirsch A. Li Q. Wudl F. Globe‐trotting Hydrogens on the Surface of the Fullerene Compound C60H6(N(CH2CH2)2O)6. Angew. Chem. Int. Ed. Engl. 1991 30 10 1309 1310 10.1002/anie.199113091
    [Google Scholar]
  98. Fukuzumi S. Electron. Transfer: Mechanisms and Applications. Weinheim Wiley 2020 10.1002/9783527651771
    [Google Scholar]
  99. Yang H.T. Ge J. Lu X.W. Sun X.Q. Miao C.B. Copper-catalyzed functionalizations of C60 with amino alcohols. J. Org. Chem. 2017 82 11 5873 5880 10.1021/acs.joc.7b00741 28493702
    [Google Scholar]
  100. Kinzyabaeva Z.S. Synthesis of 3′,3′-bis(hydroxymethyl) morpholino[5′,6′:1,9](C60-Ih)[5,6]fullerene by the oxidative addition reaction of tris(hydroxymethyl)aminomethane to C60 fullerene under the action of ultrasonic radiation. Russ. Chem. Bull. 2024 73 8 2274 2279 10.1007/s11172‑024‑4349‑9
    [Google Scholar]
  101. Elemes Y. Silverman S.K. Sheu C. Reaction of C60 with dimethyldioxirane—formation of an epoxide and a 1,3-dioxolane derivative. Angew. Chem. Int. Ed. Engl. 1992 31 351 353 10.1002/anie.199203511
    [Google Scholar]
  102. Kinzyabaeva Z.S. Fazletdinova Z.N. Sabirov D.S. Moroline adduct of fullerene C70: Sonochemical synthesis and mechanism. Bashkir Chemical J. 2023 30 15 123 130
    [Google Scholar]
  103. Kinzyabaeva Z.S. Morpholine adduct of C70 fullerene: Sonochemical synthesis and mechanism. Russ. J. Appl. Chem. 2024 97 9 724 728 10.1134/S1070427224090040
    [Google Scholar]
  104. Kinzyabaeva Z.S. Non-classical sonochemical regioselective reaction of [4 + 2]-cycloaddition in the synthesis of morpholine adducts of C70 fullerene. Fuller. Nanotub. Carbon Nanostruct. 2025 33 8 790 798 10.1080/1536383X.2025.2458511
    [Google Scholar]
  105. Friedrich J. Schweitzer P. Dinse K.P. Rapta P. Stasko A. EPR study of radical anions of C60 and C70. Appl. Magn. Reson. 1994 7 2-3 415 425 10.1007/BF03162622
    [Google Scholar]
  106. Konarev D.V. Troyanov S.I. Otsuka A. Yamochi H. Saito G. Lyubovskaya R.N. Charge transfer complexes of fullerenes containing C60˙− and C70˙− radical anions with paramagnetic CoII(dppe)2Cl+ cations (dppe: 1,2-bis(diphenylphosphino)ethane). Dalton Trans. 2016 45 15 6548 6554 10.1039/C5DT04627K 26956368
    [Google Scholar]
  107. Dubois D. Kadish K.M. Flanagan S. Haufler R.E. Chibante L.P.F. Wilson L.J. Spectroelectrochemical study of the C60 and C70 fullerenes and their mono-, di-, tri- and tetraanions. J. Am. Chem. Soc. 1991 113 11 4364 4366 10.1021/ja00011a069
    [Google Scholar]
  108. Brezová V. Dvoranová D. Rapta P. Staško A. Photoinduced electron transfer between C70 fullerene and 3,3′,5,5′-tetramethylbenzidine studied by electron paramagnetic resonance. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2000 56 14 2729 2739 10.1016/S1386‑1425(00)00317‑6 11145340
    [Google Scholar]
  109. Baumgarten M. Gherghel L. Electronic properties of charged fullerenes characterized by EPR and Vis-NIR spectroscopy. Appl. Magn. Reson. 1996 11 2 171 182 10.1007/BF03162052
    [Google Scholar]
  110. Lobach A.S. Goldshleger N.F. Kaplunov M.G. Kulikov A.V. Reduction of C60 and C70 by primary amines: Optical and ESR studies. Russ. Chem. Bull. 1996 45 1 93 98 10.1007/BF01433740
    [Google Scholar]
  111. Kinzyabaeva Z.S. Dmitriev A.M. Sabirov D.S. A sonochemical synthesis of the piperazine-containing adducts of the C60 fullerene. Fuller. Nanotub. Carbon Nanostruct. 2021 29 8 601 607 10.1080/1536383X.2021.1873782
    [Google Scholar]
  112. Kinzyabaeva Z.S. Sonochemical synthesis of 1′,4′-dialkyl-1′,4′,5′,6′-tetrahydropyrazino[2′,3′:1,9](C60-Ih)[5,6]fullerenes. Chem. Heterocycl. Compd. 2021 57 5 602 605 10.1007/s10593‑021‑02950‑2
    [Google Scholar]
  113. Kinzyabaeva Z.S. Sharipov G.L. Method for producing 2,3-fullero[60]-1,4- diazabicyclo[2.2.2]octane. DE patent 3867417D1 2021
  114. Kinzyabaeva Z.S. Sharipov G.L. Method for producing 1,9-N,N’-diethylethylenediamino-1,9-dihydro-(C60-Ih)[5,6]fullerene. RU Patent 2767540 2022
  115. Kinzyabaeva Z.S. Akhmetov A.R. Sonochemical isomerization of [5,6]-open adducts of C60 fullerene with camphor derivatives into [6,6]-closed ones. Curr. Org. Chem. 2025 29 2 135 143 10.2174/0113852728338711240815062515
    [Google Scholar]
  116. Akhmetov A.R. Kinzyabaeva Z.S. Selective catalytic synthesis of Hydrocarbons based on C60 fullerene and adamantane in the presence of Pd(PPh3)2Cl2 and their sonochemical isomerization. Curr. Org. Chem. 2025 29 13 1042 1049 10.2174/0113852728346078241011054350
    [Google Scholar]
  117. Chendke P.K. Fogler H.S. Sonoluminescence and sonochemical reactions of aqueous carbon tetrachloride solutions. J. Phys. Chem. 1983 87 8 1362 1369 10.1021/j100231a019
    [Google Scholar]
  118. Francony A. Pétrier C. Sonochemical degradation of carbon tetrachloride in aqueous solution at two frequencies: 20 kHz and 500 kHz. Ultrason. Sonochem. 1996 3 2 S77 S82 10.1016/1350‑1477(96)00010‑1
    [Google Scholar]
/content/journals/coc/10.2174/0113852728425497251201060521
Loading
/content/journals/coc/10.2174/0113852728425497251201060521
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test