Spokoyny, Alexander M.

Inorganic

Spokoyny Alexander

Biography

 

Dr. Alexander Spokoyny was born and spent his childhood and teenage years in Moscow, Russia. After his family immigrated to United States in 2001, Alex attended UCLA, where he was introduced to the area of boron cluster chemistry working as an undergraduate researcher in the laboratory of Prof. M. Frederick Hawthorne. He continued his graduate chemistry education at Northwestern University under the guidance of Prof. Chad A. Mirkin. At Northwestern, Alex developed new materials, devices, and fundamentally new classes of ligand platforms based on organomimetic carborane clusters. Upon receiving his Ph.D. in inorganic chemistry in 2011, Alex decided to move further east, where he was an NIH Post-Doctoral Fellow working in the laboratories of Profs. Stephen L. Buchwald and Bradley L. Pentelute at MIT. There his research interests involved the development of new bioconjugation strategies for peptides and proteins and regulation of protein-protein interactions. Alex has been a faculty at UCLA since 2014.

Research Interests

Our research program encompasses an interdisciplinary approach focusing on pressing problems in chemistry, biology, medicine and materials science. To tackle these challenges, we are exploring fundamentally new synthetic avenues, structural understanding, and applications for inorganic and organomimetic clusters. We focus on the development of an extensive and versatile synthetic toolbox, allowing for the functionalization of various polyhedral borane and carborane 3D cluster motifs. Specifically, we are currently working on new ligand platforms with unique electronic and steric features, stable inorganic radicals, and multifunctional, atomically precise nanosized molecules. These research efforts will reveal novel and potentially useful solutions to important problems in science and technology, including: new reaction development, energy storage and biomolecular recognition and labeling.

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Honors & Awards

  • Fellow (RSC) (2024)
  • IIN Trailblazer Award, International Institute for Nanotechnology, Northwestern University (2023-24)
  • UCLA Community Service and Praxis DEI Award (2022)
  • UCLA Distinguished Teaching Award (2021)
  • Camille Dreyfus Teacher-Scholar Award (2020)
  • UCLA Undergraduate Faculty Mentor Award (2020)
  • Thieme Chemistry Journal Award (2020)
  • National Science Foundation CAREER Award (2019)
  • Hanson-Dow Award for Outstanding Teaching (2019)
  • Inorganic Chemistry (ACS), Emerging Investigator (2019)
  • Chemical Communications (RSC), Emerging Investigator (2019)
  • Cottrell Scholar, Research Corporation for Science Advancement (2018)
  • NIH/NIGMS Maximizing Investigators Research Award (MIRA) (2017)
  • Alfred P. Sloan Foundation Research Fellowship (2017)
  • Glenn T. Seaborg Award, UCLA (2017)
  • Krug Lectureship, University of Illinois, Urbana Champaign (2017)
  • Chemical and Engineering News (C&EN), Talented 12 (2016)
  • ACS Petroleum Research Fund, Doctoral New Investigator Grant (2016)
  • 3M Non-Tenured Faculty Award (2016)
  • Inorganic Chemistry Frontiers, Emerging Investigator (2015)
  • NIH Ruth Kirschstein NRSA Post-Doctoral Fellowship (2012 – 2014)
  • Best Poster Prize, 23rd American Peptide Symposium, Hawaii, USA (2013).
  • IUPAC Prize for Young Chemists (2012)
  • Award for Excellence in Graduate Research, Northwestern Univ., Chemistry Department (2011)
  • Finalist, Young Boron Chemist Award, XIV International Conference on Boron Chemistry (2011)
  • Selected for Poster Talk at Organometallic Chemistry Gordon Research Conference (2011)
  • Young Investigator Award, American Chemical Society, Division of Inorganic Chemistry (2011)
  • JSPS Global Center of Excellence Visiting Fellowship, University of Tokyo (2011)
  • E. W. Gelewitz Award for Excellence in Graduate Studies, Northwestern University (2010)
  • Presidential Fellowship, Northwestern University (2010 – 2011)
  • Society of Fellows, Northwestern University (2010 – present)
  • GAANN Fellowship, U. S. Department of Education, Northwestern University (2006 – 2007)

Representative Publications

Below is the list of the most recent and selected publications.  For the full list, please visit here.

  • Tilden, J. A. R.; Doud, E. A.; Montgomery, H. R.; Maynard, H. D.; Spokoyny, A. M. “Organometallic Chemistry Tools for Building Biologically-Relevant Nanoscale Systems”, under review. 
  • Montgomery, H. R.; Spokoyny, A. M.; Maynard, H. D. “Organometallic Oxidative Addition Complexes for S-Arylation of Free Cysteines”, Bioconjugate Chem. 2024, in press. 
  • Kunkel, G. E.; Zhou, Q.; Treacy, J. W.; Montgomery, H. R.; Salas-Ambrosio, P.; Ready, A. D.; Spokoyny, A. M.; Houk, K. N.; Maynard, H. D. “Comparison of Cyclic and Linear PEG Conjugates”, Bioconjugate Chem. 2024, 35, 744-749.
  • Sica, A. V.; Hua, A. S.; Coffey, B.; Anderson, K. P.; Nguyen, B. T.; Spokoyny, A. M.; Caram, J. R. “Measuring the Total Photon Economy of Molecular Species through Fluorescent Optical Cycling (FOC)”, under review. 
  • Zhu, M.; Wang, P.; Wu, Z.; Zhong, Y.; Su, L.; Xin, Y.; Spokoyny, A. M.; Zou, C.; Mu, X. “A Pd-Catalyzed Route to Carborane-Fused Boron Heterocycles”, Chem. Sci. 2024, online. 
  • Earley, J. D.; Reid, O. G.; Murrey, T. L.; Doud, E. A.; Spokoyny, A. M.; Hermosilla-Palacios, M. A.; Rumbles, G.; Ferguson, A. J.; Blackburn, J. L. “Efficient Free Charge Generation at Low-Carrier Concentration in Chemically-Doped Single-Walled Carbon Nanotubes”, under review. 
  • Earley, J. D.; Reid, O. G.; Murrey, T. L.; Doud, E. A.; Spokoyny, A. M.; Hermosilla-Palacios, M. A.; Rumbles, G.; Ferguson, A. J.; Blackburn, J. L. “Efficient Free Charge Generation at Low-Carrier Concentration in Chemically-Doped Single-Walled Carbon Nanotubes”, under review. 
  • Doud, E. A.; Tilden, J. A. R.; Treacy, J. W.; Chao, E. Y.; Montgomery, H. R.; Kunkel, G. E.; Oliveres, E. J.; Adhami, N.; Kerr, T. A.; Chen, Y.; Rheingold, A. L.; Loo, J. A.; Frost, C. G.; Houk, K. N.; Maynard, H. D.; Spokoyny, A. M. “Ultrafast Au(III)-Mediated Arylation of Cysteine”, J. Am. Chem. Soc. 2024, 146, 18, 12365-12374. Preprint: http://doi.org/10.26434/chemrxiv-2023-brjnz.
  • Ready, A. D.; Nelson, Y. A.; Pomares, D. F. T.; Spokoyny, A. M. “Redox-Active Boron Clusters”, Acc. Chem. Res. 2024, 57, 9, 1310-1324.
  • Baublis, A. J.; Spokoyny, A. M. “Boron Cluster Organocatalysis”, Chem. 2024, 10, 29-32.
  •  Kunkel, G. E.; Tracy, J. W.; Montgomery, H. R.; Puente, E. G.; Doud, E. A.; Spokoyny, A. M.; Maynard, H. D. “Efficient End-Group Functionalization and Diblock Copolymer Synthesis via Au(III) Polymer Reagents”, Chem. Commun. 2024, 60, 79-82. 
  • Hermosilla-Palacios, M A.; Martinez, M.; Doud, E. A.; Hertel, T.; Spokoyny, A. M.; Cambre, S.; Wenseleers, W.; Kim, Y.-H.; Ferguson, A. J.; Blackburn, J. L. “Carrier Density and Delocalization Signatures in Doped Carbon Nanotubes from Quantitative Magnetic Resonance”, Nanoscale Horiz. 2024, 9, 278-284.
  • Nelson, Y. A.; Irshad, A.; Kim, S.; Waddington, M. A.; Salamat, C. Z.; Gembicky, M.; Rheingold, A. L.; Carta, V. ; Tolbert, S.; Narayan, S.; Spokoyny, A. M. “Vertex Differentiation Strategy for Tuning the Physical Properties of closo-Dodecaborate Weakly Coordinating Anions”, Inorg. Chem. 2023, 62, 15084-15093. Preprint: https://doi.org/10.26434/chemrxiv-2023-qngkp.
  • Ready, A. D.; Irshad, A.; Kallistova, A.; Carrillo, M.; Gembicky, M.; Seshadri, R.; Narayan, S.; Spokoyny, A. M. “Electrochemical Cycling of Redox-Active Boron Cluster-Based Materials in the Solid State”, J. Am. Chem. Soc. 2023, 145, 14345-14353. Preprint: https://doi.org/10.26434/chemrxiv-2023-1j61f.
  • Murray, T. L.; Aubry, T. J.; Leon Ruiz, O.; Thurman, K.; Eckstein, K. H.; Doud, E. A.; Stauber, J. M.; Spokoyny, A. M.; Schwartz, B. J.; Hertel, T.; Blackburn, J. L.; Ferguson, A. J. “Tuning Counterion Chemistry to Reduce Carrier Localization in Doped Thermoelectric Carbon Nanotube Networks”, Cell Rep. Phys. Sci. 2023, 4, 101407. Preprint via CellPress Sneak Peek: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4287840​.
  •  Kim, S.; Treacy, J.; Nelson, Y.; Gonzalez, J.; Gembicky, M.; Houk, K. N.; Spokoyny, A. M. “Arene C–H Borylation Strategy Enabled by a Non-Classical Boron Cluster-Based Electrophile”, Nature Comm. 2023, 14, 1671. Preprint: https://doi.org/1026434/chemrxiv-2022-j5t74.
  • Montgomery. H. R.; Messina, M. S.; Doud, E. A.; Spokoyny, A. M.*; Maynard. H. D.* “Organometallic S-Arylation Reagents for Rapid PEGylation of Biomolecules”, Bioconjugate Chem. 2022, 33, 1536-1542.
  • McDaniel, J. W.; Stauber, J. M.; Doud, E. A.; Spokoyny, A. M.*; Murphy, J. M.* “An Organometallic Gold (III) Reagent for 18F-Labeling of Unprotected Peptides and Sugars in Aqueous Media”, Org. Lett. 2022, 24, 5132-5136.
  • Anderson, K. P.; Rheingold, A. L.; Djurovich, P. I.; Soman, O.; Spokoyny, A. M.* “Filling in the Gaps: Synthesis and Luminescence of Monohalogenated B18H22 Clusters”, Polyhedron 2022, in press. (Special Issue in Honor of Professor Arnold Rheingold)
  • Anderson, K. P.; Djurovich, P. I.; Rubio, V. P.; Liang, A.; Spokoyny, A. M.* “Metal-Catalyzed and Metal-Free Nucleophilic Substitution of 7-I-B18H22“, Inorg. Chem. 2022, in press.
  • Wang, Y.; Spokoyny, A. M.* “Abiotic Main Group Pharmacophore Renders a New Class of Antimicrobial Agents”, (First Reactions) ACS Cent. Sci. 2022, 8, 309-311.
  • Ready, A. D.; Becwar, S. M.; Jung, D.; Kallistova, A.; Schueller, E.; Anderson, K. P.; Kubena, R.; Seshadri, R.; Chmelka, B. F.*; Spokoyny, A. M.* “Synthesis and Structural Properties of a 2D Zn(II) Dodecahydroxy-Closo-Dodecaborate Coordination Polymer”, Dalton Trans. 2022, 51, 11547-11557.
  • Mills, H. A.; Jones, C. G.; Anderson, K. P.; Ready, A. D.; Djurovic, P. I.; Khan, S. I.; Hohman, J. N.*; Nelson, H. M.*; Spokoyny, A. M.* “Sterically Invariant Carborane-Based Ligands for the Morphological and Electronic Control of Metal-Organic Chalcogenolate Assemblies”, Chem. Mater. 2022, 34, 6933-6943. ​
  • Anderson, K. P.; Hua, A. S.; Plumley, J. B.; Ready, A. D.; Rheingold, A. L.; Peng, T. L.; Djurovich, P. I.; Kerestes, C.; Snyder, N. A.; Andrews, A.; Caram, J. R.*; Spokoyny, A. M.* “Benchmarking the Dynamic Luminescent Properties and UV Stability of B18H22-based Materials”, Dalton. Trans. 2022, 51, 9223-9228.
  • Mills, H. A.; Alsarhan, F.; Ong, T.-C.; Gembicky, M.; Rheingold, A. L.; Spokoyny, A. M.* “Icosahedral Meta-Carboranes Containing Exopolyhedral B-Se and B-Te Bonds”, Inorg. Chem. 2021, 60, 19165-19174. 
  • Bernier, N. A.; Teh, J.; Reichel, D.; Zahorsky-Reeves, J. L.; Perez, J. M.* Spokoyny, A. M.* “Ex Vivo and in Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles”, Langmuir 2021, 37, 14500-14508. 
  • Waddington, M. A.; Zheng, A.; Stauber, J. M.; Moully, E. H.; Saleh, L. M. A.; Král, P.; Spokoyny, A. M. “Cysteine Borylation in Unprotected Peptides”, J. Am. Chem. Soc. 2021, 143, 8661-8668.
  • Kataki-Anastasakou, A.; Axtell, J. C.; Hernandez, S.; Dziedzic, R. M.; Balaich, G. J.; Rheingold, A. L.; Spokoyny, A. M.; Sletten, E. M. “Carborane Guests for Cucurbit[7]uril Facilitate Strong Binding and on Demand Removal”, J. Am. Chem. Soc.2020, 142, 20513-20518.
  • Stauber, J. M.; Schwan, J.; Zhang, X.; Axtell, J. C.; Jung, D.; McNicholas, B. J.; Oyala, P. H.; Martinolich, A. J.; Winkler, J. R.; See, K. A.; Miller, T. F.; Gray, H. B.; Spokoyny, A. M. “A Super-Oxidized Radical Cationic Icosahedral Boron Cluster”, J. Am. Chem. Soc. 2020, 142, 12948-12953.
  • Mills, H. A.; Martin, J. L.; Rheingold, A. L.; Spokoyny, A. M. “Oxidative Generation of Boron-Centered Radicals in Carboranes”, J. Am. Chem. Soc. 2020, 142, 4586-4591.
  • Stauber, J. M.; Qian, E. A.; Han, Y.; Rheingold, A. L.; Král, P.; Fujita, D.; Spokoyny, A. M. “An Organometallic Strategy for Assembling Atomically Precise Hybrid Nanomaterials”, J. Am. Chem. Soc. 2020, 142, 327-334.
  • Mu, X.; Axtell, J. C.; Bernier, N. A.; Kirlikovali, K. O.; Jung, D.; Umanzor, A.; Chen, X.; Bay, K. L.; Kirollos, M.; Rheingold, A. L.; Houk, K. N.; Spokoyny, A. M. “Sterically Unprotected Nucleophilic Boron Cluster Reagents”, Chem 2019, 5, 2461-2469.
  • Aubry, T. J.; Axtell, J. C.; Basile, V. M.; Winchell, K. J.; Lindemuth, J. R.; Porter, T. M.; Liu, J.-Y.; Alexandrova, A. N.; Kubiak, C. P.; Tolbert, S. H.; Spokoyny, A. M.; Schwartz, B. J. “Dodecaborane-Based Dopants Designed to Shield Anion Electrostatics to Increased Carrier Mobility in Doped Conjugated Polymers”, Adv. Mater. 2019, 31, 1805647 (1-8).
  • Jung, D.; Saleh, L. M. A.; Berkson, Z.; El-Kady, M. F.; Hwang, J. Y.; Mohamed, N.; Wixtrom, A. I.; Titarenko, E.; Shao, Y.; McCarthy, K.; Guo, J.; Martini, I. B.; Kraemer, S.; Wegener, E. C.; Saint-Crieq, P.; Ruehle, B.; Langeslay, R. R.; Delferro, M.; Brosmer, J. L.; Hendon, C. H.; Gallagher-Jones, M.; Rodriguez, J.; Chapman, K. W.; Miller, J. T.; Duan, X.; Kaner, R. B.; Zink, J. I.; Chmelka, B. F.; Spokoyny, A. M. “A Molecular Cross-Linking Approach for Hybrid Metal Oxides”, Nature Materials 2018, 17, 341-348.
  • Messina, M. S.; Stauber, J. M.; Waddington, M. A.; Rheingold, A. L.; Maynard, H. D.; Spokoyny, A. M. “Organometallic Gold(III) Reagents for Cysteine Arylation”, J. Am. Chem. Soc. 2018, 140, 7065-7069.
  • Dziedzic, R. M.; Martin, J. L.; Axtell, J. C.; Saleh, L. M. A.; Yang, Y.; Messina, M.; Houk, K. N.; Spokoyny, A. M. “Cage-Walking: Vertex Differentiation by Palladium-Catalyzed Isomerization of B(9)-Bromo-meta-Carborane”, J. Am. Chem. Soc. 2017, 139, 7729-7732.
  • Qian, E. A.; Wixtrom, A. I.; Axtell, J. C.; Saebi, A.; Rehak, P.; Han, Y.; Moully, E. H.; Mosallaei, D.; Chow, S.; Messina, M.; Wang, J.-Y.; Royappa, A. T.; Rheingold, A. L.; Maynard, H. D.; Kral, P.; Spokoyny, A. M. “Atomically Precise Organomimetic Cluster Nanomolecules Assembled via Perfluoroaryl-Thiol SNAr Chemistry”, Nature Chem. 2017, 9, 333-340.
  • em>Axtell, J. C.; Kirlikovali, K. O.; Djurovich, P. I.; Jung, D.; Nguyen, V. T.; Munekiyo, B.; Royappa, A. T.; Rheingold, A. L.; Spokoyny, A. M. “Blue Phosphorescent Zwitterionic Iridium(III) Complexes Featuring Weakly Coordinating Carborane-based Ligands”, J. Am. Chem. Soc. 2016, 138, 15758-15765.
  • Dziedzic, R.; Saleh, L.; Axtell, J.; Martin, J.; Stevens, S.; Royappa, A.; Rheingold, A.; Spokoyny, A. M. “B-N, B-O and B-CN Bond Formation via Palladium Catalyzed Cross-Coupling of B-Bromo-Carboranes”, J. Am. Chem. Soc. 2016, 138, 9081-9084.
  • Messina, M. S.; Axtell, J. C.; Wang, Y.; Chong, P.; Wixtrom, A. I.; Kirlikovali, K. O.; Upton, B. M.; Hunter, B. M.; Shafaat, O. S.; Khan, S. I.; Winkler, J. R.; Gray, H. B.; Alexandrova, A. N.; Maynard, H. D.; Spokoyny, A. M. “Visible-Light Induced Olefin Activation using 3D Aromatic Boron-Rich Cluster Photooxidants”, J. Am. Chem. Soc. 2016, 138, 6952-6955.
  • Vinogradova, E. V.; Zhang, C.; Spokoyny, A. M.; Pentelute, B. L.; Buchwald, S. L. “Organometallic Palladium Reagents for Cysteine Bioconjugation”, Nature 2015, 526, 687-691