Earlier Work: Chemistry (2002–2019)

Peer-reviewed publications, book chapters, and patents from a prior research career in fullerene and fluoroorganic chemistry.

Before moving into data science and industrial decision systems, I spent the first part of my career as a research chemist, working on the synthesis and characterization of fullerene derivatives and other fluoroorganic compounds. I left the laboratory in 2013; co-authored work continued to appear for several years afterward. This page preserves the record of that career: 49 peer-reviewed journal articles, 3 book chapters, 2 patents, and a book translation.

Journal articles

  1. PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals. Karlee P. Castro, Eric V. Bukovsky, Igor V. Kuvychko, Nicholas J. DeWeerd, Yu-Sheng Chen, Shihu H. M. Deng, Xue-Bin Wang, Alexey A. Popov, Steven H. Strauss, Olga V. Boltalina. doi:10.1002/chem.201902712
  2. Steric and electronic effects of CF3 conformations in acene (CF3)n derivatives. N. J. DeWeerd, E. V. Bukovsky, K. P. Castro, I. V. Kuvychko, A. A. Popov. Journal of Fluorine Chemistry 2019, 221, 1-7. doi:10.1016/j.jfluchem.2019.02.010
  3. Fluorination-Induced Evolution of Columnar Packing in Fluorous Triphenylenes and Benzotriphenylenes. K. C. Rippy, N. J. DeWeerd, I. V. Kuvychko, Y.-S. Chen, S. H. Strauss, O. V. Boltalina. ChemPlusChem 2018, 83 (12), 1067-1077. doi:10.1002/cplu.201800451
  4. Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene. I. V. Kuvychko, T. Clikeman, C. Dubceac, Y.-S. Chen, M. A. Petrukhina. European Journal of Organic Chemistry 2018 (31), 4233-4245.
  5. Experimental and DFT Studies of the Electron-Withdrawing Ability of Perfluoroalkyl (RF) Groups: Electron Affinities of PAH(RF)n Increase Significantly with Increasing RF. L. K. San, S. N. Spisak, C. Dubceac, S. H. M. Deng, I. V. Kuvychko, M. A. Petrukhina. Chemistry–A European Journal 24 (6), 1441-1447.
  6. Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two Complementary π-Bowls. C. Dubceac, Y. Sevryugina, I. V. Kuvychko, O. V. Boltalina, S. H. Strauss. Crystal Growth & Design 18 (1), 307-311.
  7. Castro, K. P.; Clikeman, T. T.; DeWeerd, N. J.; Bukovsky, E. V.; Rippy, K. C.; Kuvychko, I. V.; Hou, G.-L.; Chen, Y.-S.; Wang, X.-B.; Strauss, S. H.; Boltalina, O. V. Incremental Tuning Up of Fluorous Phenazine Acceptors. Chem. Eur. J. 2016, 22, 3930–3936.
  8. Boltalina, O. V.; Popov, A. A.; Kuvychko, I. V.; Shustova, N. B.; Strauss, S. H. Perfluoroalkylfullerenes. Chemical Reviews 2015, 115, 1051-1105.
  9. Whitaker, J. B.; Kuvychko, I. V.; Shustova, N. B.; Chen, Y.-S.; Strauss, S. H.; Boltalina, O. V. An elusive fulvene 1,7,11,24-C-60(CF3)(4) and its unusual reactivity. Chemical Communications 2014, 50, 1205-1208.
  10. San, L. K.; Bukovsky, E. V.; Kuvychko, I. V.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Single-Step Gas-Phase Polyperfluoroalkylation of Naphthalene Leads to Thermodynamic Products. Chemistry-a European Journal 2014, 20, 4373-4379.
  11. Clikeman, T. T.; Bukovsky, E. V.; Kuvychko, I. V.; San, L. K.; Deng, S. H. M.; Wang, X.-B.; Chen, Y.-S.; Strauss, S. H.; Boltalina, O. V. Poly(trifluoromethyl) azulenes: structures and acceptor properties. Chemical Communications 2014, 50, 6263-6266.
  12. Kuvychko, I. V.; Dubceac, C.; Deng, S. H. M.; Wang, X.-B.; Granovsky, A. A.; Popov, A. A.; Petrukhina, M. A.; Strauss, S. H.; Boltalina, O. V. C20H4(C4F8)(3): A Fluorine-Containing Annulated Corannulene that Is a Better Electron Acceptor Than C-60. Angewandte Chemie-International Edition 2013, 52, 7505-7508.
  13. Kuvychko, I. V.; Castro, K. P.; Deng, S. H. M.; Wang, X.-B.; Strauss, S. H.; Boltalina, O. V. Taming Hot CF3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics. Angewandte Chemie-International Edition 2013, 52, 4871-4874.
  14. Clikeman, T. T.; Kuvychko, I. V.; Shustova, N. B.; Chen, Y.-S.; Popov, A. A.; Boltalina, O. V.; Strauss, S. H. Regioselective Sequential Additions of Nucleophiles and Electrophiles to Perfluoroalkylfullerenes: Which Cage C Atoms Are the Most Reactive and Why? Chemistry-a European Journal 2013, 19, 5070-5080.
  15. Kuvychko, I. V.; Whitaker, J. B.; Larson, B. W.; Folsom, T. C.; Shustova, N. B.; Avdoshenko, S. M.; Chen, Y.-S.; Wen, H.; Wang, X.-B.; Dunsch, L.; Popov, A. A.; Boltalina, O. V.; Strauss, S. H. Substituent effects in a series of 1,7-C-60(R-F)(2) compounds (R-F = CF3, C2F5, n-C3F7, i-C3F7, n-C4F9, s-C4F9, n-C8F17): electron affinities, reduction potentials and E(LUMO) values are not always correlated. Chemical Science 2012, 3, 1399-1407.
  16. Kuvychko, I. V.; Strauss, S. H.; Boltalina, O. V. Solution-phase perfluoroalkylation of C-60 leads to efficient and selective synthesis of bis-perfluoroalkylated fullerenes. Journal of Fluorine Chemistry 2012, 143, 103-108.
  17. Kuvychko, I. V.; Spisak, S. N.; Chen, Y.-S.; Popov, A. A.; Petrukhina, M. A.; Strauss, S. H.; Boltalina, O. V. A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5. Angewandte Chemie-International Edition 2012, 51, 4939-4942.
  18. Shustova, N. B.; Peryshkov, D. V.; Kuvychko, I. V.; Chen, Y.-S.; Mackey, M. A.; Coumbe, C. E.; Heaps, D. T.; Confait, B. S.; Heine, T.; Phillips, J. P.; Stevenson, S.; Dunsch, L.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Poly(perfluoroalkylation) of Metallic Nitride Fullerenes Reveals Addition-Pattern Guidelines: Synthesis and Characterization of a Family of Sc3N@C-80(CF3)(n) (n=2-16) and Their Radical Anions. Journal of the American Chemical Society 2011, 133, 2672-2690.
  19. Shustova, N. B.; Kuvychko, I. V.; Popov, A. A.; von Delius, M.; Dunsch, L.; Anderson, O. P.; Hirsch, A.; Strauss, S. H.; Boltalina, O. V. Nitrogen Directs Multiple Radical Additions to the 9,9’-Bi-1-aza(C-60-I-h) 5,6 fullerene: X-ray Structure of 6,9,12,15,18-C59N(CF3)(5). Angewandte Chemie-International Edition 2011, 50, 5537-5540.
  20. Shustova, N. B.; Kuvychko, I. V.; Peryshkov, D. V.; Whitaker, J. B.; Larson, B. W.; Chen, Y.-S.; Dunsch, L.; Seppelt, K.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Chemical tailoring of fullerene acceptors: synthesis, structures and electrochemical properties of perfluoroisopropylfullerenes. Chemical Communications 2011, 47, 875-877.
  21. Kuvychko, I. V.; Whitaker, J. B.; Larson, B. W.; Raguindin, R. S.; Suhr, K. J.; Strauss, S. H.; Boltalina, O. V. Pressure effect on heterogeneous trifluoromethylation of fullerenes and its application. Journal of Fluorine Chemistry 2011, 132, 679-685.
  22. Kuvychko, I. V.; Shustova, N. B.; Avdoshenko, S. M.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. In Search of Fullerene-Based Superacids: Synthesis, X-ray Structure, and DFT Study of C-60(C2F5)(5)H. Chemistry-a European Journal 2011, 17, 8799-8802.
  23. Wang, X.-B.; Chi, C.; Zhou, M.; Kuvychko, I. V.; Seppelt, K.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V.; Wang, L.-S. Photoelectron Spectroscopy of C60Fn- and C60Fm2- (n=17, 33, 35, 43, 45, 47; m=34, 46) in the Gas Phase and the Generation and Characterization of C-1-C60F47- and D-2-C60F44 in Solution. Journal of Physical Chemistry A 2010, 114, 1756-1765.
  24. Shustova, N. B.; Kareev, I. E.; Kuvychko, I. V.; Whitaker, J. B.; Lebedkin, S. F.; Popov, A. A.; Dunsch, L.; Chen, Y.-S.; Seppelt, K.; Strauss, S. H.; Boltalina, O. V. High-temperature and photochemical syntheses of C-60 and C-70 fullerene derivatives with linear perfluoroalkyl chains. Journal of Fluorine Chemistry 2010, 131, 1198-1212.
  25. Kuvychko, I. V.; Streletskii, A. V.; Shustova, N. B.; Seppelt, K.; Drewello, T.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Soluble Chlorofullerenes C60Cl2,4,6,8,10. Synthesis, Purification, Compositional Analysis, Stability, and Experimental/Theoretical Structure Elucidation, Including the X-ray Structure of C-1-C60Cl10. Journal of the American Chemical Society 2010, 132, 6443-6462.
  26. Kuvychko, I. V.; Popov, A. A.; Streletskii, A. V.; Nye, L. C.; Drewello, T.; Strauss, S. H.; Boltalina, O. V. Dynamic HPLC study of C-70 chlorination reveals a surprisingly selective synthesis of C70Cl8. Chemical Communications 2010, 46, 8204-8206.
  27. Kareev, I. E.; Popov, A. A.; Kuvychko, I. V.; Shustova, N. B.; Lebedkin, S. F.; Bubnov, V. P.; Anderson, O. P.; Seppelt, K.; Strauss, S. H.; Boltalina, O. V. Synthesis and X-ray or NMR/DFT structure elucidation of twenty-one new trifluoromethyl derivatives of soluble cage isomers of C-76, C-78, C-84, and C-90. Journal of the American Chemical Society 2008, 130, 13471-13489.
  28. Kareev, I. E.; Kuvychko, I. V.; Shustova, N. B.; Lebedkin, S. F.; Bubnov, V. P.; Anderson, O. P.; Popov, A. A.; Boltalina, O. V.; Strauss, S. H. C(1)-(C(84)-C(2)(11))(CF(3))(12): Trifluoromethylation yields structural proof of a minor C(84) cage and reveals a principle of higher fullerene reactivity. Angewandte Chemie-International Edition 2008, 47, 6204-6207.
  29. Shustova, N. B.; Kuvychko, I. V.; Boltalina, O. V.; Strauss, S. H. 1,7,16,30,36,47-hexakis(perfluoroisopropyl)-1,7,16,30,36,47-hexahydro(C-60-I-h) 5,6 fullerene. Acta Crystallographica Section E-Structure Reports Online 2007, 63, O4575-U3839.
  30. Shustova, N. B.; Kuvychko, I. V.; Bolskar, R. D.; Seppelt, K.; Strauss, S. H.; Popov, A. A.; Boltalina, O. V. Trifluoromethyl derivatives of insoluble small-HOMO-LUMO-gap hollow higher fullerenes. NMR and DFT structure elucidation of C-2-(C-74-D-3h)(CF3)(12), C-s-(C-76-T-d(2))(CF3)(12), C-2-(C-78-D-3h(5))(CF3)(12), C-s-(C-80-C-2v(5))(CF3)(12), and C-2-(C-82-C-2(5))(CF3)(12). Journal of the American Chemical Society 2006, 128, 15793-15798.
  31. Kareev, I. E.; Shustova, N. B.; Kuvychko, I. V.; Lebedkin, S. F.; Miller, S. M.; Anderson, O. P.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Thermally stable perfluoroalkylfullerenes with the skew-pentagonal-pyramid pattern: C-60(C2F5)(4)O, C-60(CF3)(4)O, and C-60(CF3)(6). Journal of the American Chemical Society 2006, 128, 12268-12280.
  32. Kareev, I. E.; Kuvychko, I. V.; Lebedkin, S. F.; Miller, S. M.; Anderson, O. P.; Strauss, S. H.; Boltalina, O. V. Synthesis and structures of poly(perfluoroethyl) 60 fullerenes: 1,7,16,36,46,49-C-60(C2F5)(6) and 1,6,11,18,24,27,32,35-C-60(C2F5)(8). Chemical Communications 2006, 308-310.
  33. Goryunkov, A. A.; Kareev, I. E.; Ioffe, I. N.; Popov, A. A.; Kuvychko, I. V.; Markov, V. Y.; Goldt, I. V.; Pimenova, A. S.; Serov, M. G.; Avdoshenko, S. M.; Khavrel, P. A.; Sidorov, L. N.; Lebedkin, S. F.; Mazej, Z.; Zemva, B.; Strauss, S. H.; Boltalina, O. V. Reaction of C-60 with KMnF4 - Isolation and characterization of a new isomer of C60F8 and re-evaluation of the structures of C60F7(CF3) and the known isomer of C60F8. Journal of Fluorine Chemistry 2006, 127, 1423-1435.
  34. Dorozhkin, E. I.; Ignat’eva, D. V.; Tamm, N. B.; Goryunkov, A. A.; Khavrel, P. A.; Ioffe, I. N.; Popov, A. A.; Kuvychko, I. V.; Streletskiy, A. V.; Markov, V. Y.; Spandl, J.; Strauss, S. H.; Boltalina, O. V. Synthesis, characterization, and theoretical study of stable isomers of C-70(CF3)(n) (n=2, 4, 6, 8, 10). Chemistry-a European Journal 2006, 12, 3876-3889.
  35. Kuvychko, I. V.; Streletskii, A. V.; Popov, A. A.; Kotsiris, S. G.; Drewello, T.; Strauss, S. H.; Boltalina, O. V. Seven-minute synthesis of pure C-s,-C60Cl6 from 60 fullerene and iodine monochloride: First IR, Raman, and mass spectra of 99 mol % C60Cl6. Chemistry-a European Journal 2005, 11, 5426-5436.
  36. Kareev, I. E.; Quinones, G. S.; Kuvychko, I. V.; Khavrel, P. A.; Ioffe, I. N.; Goldt, I. V.; Lebedkin, S. F.; Seppelt, K.; Strauss, S. H.; Boltalina, O. V. Variable-temperature F-19 NMR and theoretical study of 1,9- and 1,7-C60F(CF3) and C-s- and C-1-C60F17(CF3): Hindered CF3 rotation and through-space J(FF) coupling. Journal of the American Chemical Society 2005, 127, 11497-11504.
  37. Kareev, I. E.; Lebedkin, S. F.; Bubnov, V. P.; Yagubskii, E. B.; Ioffe, I. N.; Khavrel, P. A.; Kuvychko, I. V.; Strauss, S. H.; Boltalina, O. V. Trifluoromethylated endohedral metallofullerenes: Synthesis and characterization of Y@C-82(CF3)(5). Angewandte Chemie-International Edition 2005, 44, 1846-1849.
  38. Kareev, I. E.; Kuvychko, I. V.; Popov, A. A.; Lebedkin, S. F.; Miller, S. M.; Anderson, O. P.; Strauss, S. H.; Boltalina, O. V. High-temperature synthesis of the surprisingly stable C-1-C-70(CF3)(10) isomer with a para(7)-meta-para ribbon of nine C-6(CF3)(2) edge-sharing hexagons. Angewandte Chemie-International Edition 2005, 44, 7984-7987.
  39. Kareev, I. E.; Kuvychko, I. V.; Lebedkin, S. F.; Miller, S. M.; Anderson, O. P.; Seppelt, K.; Strauss, S. H.; Boltalina, O. V. Synthesis, structure, and F-19 NMR spectra of 1,3,7,10,14,17,23,28,31,40-C-60(CF3)(10). Journal of the American Chemical Society 2005, 127, 8362-8375.
  40. Streletskiy, A. V.; Goldt, I. V.; Kuvychko, I. V.; Ioffe, I. N.; Sidorov, L. N.; Drewello, T.; Strauss, S. H.; Boltalina, O. V. Application of 9-nitroanthracene as a matrix for laser desorption/ionization analysis of fluorinated fullerenes. Rapid Communications in Mass Spectrometry 2004, 18, 360-362.
  41. Popov, A. A.; Goryunkov, A. A.; Goldt, I. V.; Kareev, I. E.; Kuvychko, I. V.; Hunnius, W. D.; Seppelt, K.; Strauss, S. H.; Boltalina, O. V. Raman, infrared, and theoretical studies of fluorofullerene C60F20. Journal of Physical Chemistry A 2004, 108, 11449-11456.
  42. Goryunkov, A. A.; Markov, V. Y.; Ioffe, I. N.; Bolskar, R. D.; Diener, M. D.; Kuvychko, I. V.; Strauss, S. H.; Boltalina, O. V. C74F38: An exohedral derivative of a small-bandgap fullerene with D-3 symmetry. Angewandte Chemie-International Edition 2004, 43, 997-1000.
  43. Goryunkov, A. A.; Ioffe, I. N.; Kuvychko, I. V.; Yankova, T. S.; Markov, V. Y.; Streletskii, A. A.; Dick, D. L.; Sidorov, L. N.; Boltalina, O. V.; Strauss, S. H. Trifluoromethylated 60 fullerenes: Synthesis and characterization. Fullerenes Nanotubes and Carbon Nanostructures 2004, 12, 181-185.
  44. Denisenko, N. I.; Troyanov, S. I.; Popov, A. A.; Kuvychko, I. V.; Zemva, B.; Kemnitz, E.; Strauss, S. H.; Boltalina, O. V. T-h-C60F24. Journal of the American Chemical Society 2004, 126, 1618-1619.
  45. Vasil’ev, Y. V.; Streletskiy, A. V.; Kuvychko, I. V.; Boltalina, O. V.; Birkett, P. R.; Campbell, E. E. B.; Korobov, M. V.; Drewello, T. The influence of phenylated by-products on the MALDI analysis of chlorinated fullerenes. International Journal of Mass Spectrometry 2003, 228, 979-984.
  46. Goryunkov, A. A.; Kuvychko, I. V.; Ioffe, I. N.; Dick, D. L.; Sidorov, L. N.; Strauss, S. H.; Boltalina, O. V. Isolation of C-60(CF3)(n) (n=2, 4, 6, 8, 10) with high compositional purity. Journal of Fluorine Chemistry 2003, 124, 61-64.
  47. Darwish, A. D.; Avent, A. G.; Boltalina, O. V.; Gol’dt, I.; Kuvytchko, I.; Da Ros, T.; Street, J. M.; Taylor, R. Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; A unique six-electron cycloaddition of a fullerene involving F-2 loss. Chemistry-a European Journal 2003, 9, 2008-2012.
  48. Streletskiy, A. V.; Kouvitchko, I. V.; Esipov, S. E.; Boltalina, O. V. Application of sulfur as a matrix for laser desorption/ionization in the characterization of halogenated fullerenes. Rapid Communications in Mass Spectrometry 2002, 16, 99-102.
  49. Darwish, A. D.; Kuvytchko, I. V.; Wei, X. W.; Boltalina, O. V.; Gol’dt, I. V.; Street, J. M.; Taylor, R. Formation of 18 trannulenes derived via Bingel reactions between C60F18O isomers and CHBr(CO2Et)(2) and between C60F18 and CHX(CO2R)(2) (X = Br, Cl; R = Me, Et). Journal of the Chemical Society-Perkin Transactions 2 2002, 1118-1121.

Book chapters

  1. Kuvychko, I. V.; Larson, B. W.; Strauss, S. H.; Boltalina, O. V. “Efficient Preparation of the Highly Soluble ortho- and para-C60(CF2C6F5)2 Derivatives,” In Efficient Preparation of Fluorine Compounds; Roesky, H., Ed.; Wiley: New York, 2012, 19-21.
  2. Boltalina, O. V.; Kuvychko, I. V.; Shustova, N. B.; Strauss, S. H. Handbook of Carbon Nanomaterials. Volume 1: Syntheses and Supramolecular Systems. Volume 2: Electron Transfer and Applications. Chapter 4. Perfluoroalkylation of Fullerenes. World Scientific, 2011.
  3. Kareev, I. E.; Bubnov, V. P.; Laukhina, E. E.; Fedutin, D. N.; Yagubskii, E. B.; Lebedkin, S. F.; Kuvychko, I. V.; Strauss, S. H.; Boltalina, O. V. Trifluoromethylation of Endohedral Metallofullerenes M@C82 (M = Y, Ce): Synthesis, Isolation and Structure. In Hydrogen Materials Science and Chemistry of Carbon Nanomaterials; Veziroglu, T. N.; Zaginaichenko, S. Y.; Schur, D. V.; Baranowski, B.; Shpak, A. P.; Skorokhod, V. V.; Kale, A., Eds.; NATO Security through Science Series A: Chemistry and Biology;

Patents

  1. Strauss, S. H.; Boltalina, O. V.; Kuvychko, I. V. Modified polyaromatic hydrocarbons and polyheterocyclics for optoelectronics. US Patent 9,249,071, 2016.
  2. Polyakov, O. G.; Strauss, S. H.; Kuvychko, I. V. Carbon monoxide and olefin adsorption from hydrogen-rich fuel gas for fuel cells. U.S. Pat. Appl. 2008, US 20080156189 A1.

Book translation

  1. Mensky, M. B. Quantum Measurements and Decoherence. Kluwer Academic Publishers, Dordrecht, 2000. Translated from English to Russian (Менский М. Б. Квантовые измерения и декогеренция: Модели и феноменология. Пер. с англ. Кувычко И. В.; Физматлит, 2001).