Gilliard Research Laboratory

Synthetic Chemistry: Main-Group & Organometallic Chemistry, Bond Activation & Catalysis, Hybrid Materials

Publications

Peer-Reviewed Articles

45. Reactions of 9-Carbene-9-Borafluorene Monoanion and Selenium: Synthesis of Boryl-Substituted Selenides and Diselenides Wentz, Kelsie E.; Molino, Andrew; Freeman, Lucas A.; Dickie, Diane A.; Wilson, David J. D.; Gilliard Jr., Robert J. Inorg. Chem. 202160, 13941-13949. DOI: 10.1021/acs.inorgchem.1c02124
*ACS Editors' Choice; Inorganic Chemistry Featured Article

44. A Thermally Stable Magnesium Phosphaethynolate Grignard Complex Obi, Akachukwu D.; Machost, Haleigh R.; Dickie, Diane A.; Gilliard Jr., Robert J. Inorg. Chem. 2021, 60, 12481-12488. DOI: 10.1021/acs.inorgchem.1c01700

43. Stabilization of the Elusive 9-Carbene-9-Borafluorene Monoanion Wentz, K. E.; Molino, A.; Weisflog, S.; Aishvaryadeep, Kaur; Dickie, Diane A.; Wilson, David J. D.; Gilliard Jr., Robert J. Angew. Chem. Int. Ed. 2021, 60, 13065-13072. DOI: 10.1002/anie.202103628 *Hot Paper; Highlighted in ChemistryViews, ScienceDaily, Phys.org, EurekaAlert

42. Indirect Access to Bismuth and Antimony Carbene-Phosphaketene Adducts and their Unusual Thermal Transformation to [NHC2OCP][OCP] Walley, Jacob E.; Warring, Levi S.; Kertész, Erik; Wang, Guocang; Dickie, Diane A.; Benkő, Zoltán; Gilliard Jr., Robert J. Inorg. Chem. 2021, 60, 4733-4743. DOI: 10.1021/acs.inorgchem.0c03683

41. Surfactant Removal for Colloidal Nanocrystal Catalysts Mediated by N-Heterocyclic Carbene Godbold, Perrin; Johnson, Grayson; Obi, Akachukwu D.; Brown, Rebecca; Hwang, Sooyeon; Gilliard, Robert J.; Zhang, Sen J. Am. Chem. Soc. 2021143, 2644-2648. DOI: 10.1021/jacs.0c12278
*Highlighted in ChemistryViews

40. Soluble, Crystalline, and Thermally Stable Alkali CO2- and Carbonite (CO22-) Clusters Supported by Cyclic (Alkyl)(Amino)Carbenes  Freeman, Lucas A.; Obi, Akachukwu D.; Machost, Haleigh R.; Molino, Andrew; Nichols, Asa. W.; Dickie, Diane A.; Wilson, David J. D.; Machan, Charles W.; Gilliard, Robert J. Chem. Sci. 2021, 12, 3544-3550. DOI: 10.1039/D0SC06851A
*Invited: Themed Collection Celebrating 10 Years of Chemical Science

*Highlighted in Chemical & Engineering News

39. s-Block Multiple Bonds: Isolation of a Beryllium Imido Complex Wang, Guocang; Walley, Jacob E.;  Dickie, Diane A.; Andrew; Wilson, David J. D.; Gilliard, Robert J.Gilliard, Robert J. Angew. Chem. Int. Ed. 2021, 60, 9407-9411. DOI: 10.1002/anie.202016027. *Hot Paper
*Highlighted in Chemical & Engineering News

38. Carbodicarbene Bismaalkene Cations: Unvravelling the Complexities of Carbene versus Carbone in Heavy Pnictogen Chemsitry Walley, Jacob E.;  Warring, Levi; Wang, Guocang; Dickie, Diane A.; Pan, Sudip; Frenking, Gernot; Gilliard, Robert J. Angew. Chem. Int. Ed. 2021, 60, 6682-6690. DOI: 10.1002/anie.202014398.

37. N-Heterocyclic Carbene Mediated Ring Opening of Reduced Diazamagnesacycles Obi, Akachukwu D.; Freeman, Lucas A.; Dickie, Diane A.; Gilliard, Robert J. Organometallics 2020, 39, 4575-4583. DOI: 10.1021/acs.organomet.0c00620.

36. Tris(carbene)-stabilization of Monomeric Magnesium Cations: A Neutral, Non-tethered Ligand Approach Obi, Akachukwu D.; Walley, Jacob E.; Dickie, Diane A.; Frey, Nathan C.; Wong, Yuen Onn; Webster, Charles E.; Gilliard, Robert J. Organometallics 2020, 39, 4329-4339. DOI: 10.1021/acs.organomet.0c00462
*Special Issue: Organometallic Chemistry of the Main-Group Elements

35. An Update on the Organometallic Chemistry of the Main-Group Elements Gilliard Jr., Robert J.; Chiu, Ching-Wen  Organometallics 202039, 4123-4123. DOI: 10.1021/acs.organomet.0c00736

34. Planar, Stair-stepped, and Twisted: Modulating Structure and Photophysics in Pyrene- and Benzene-Fused N-Heterocyclic Boranes  Krantz, Kelsie E.; Weisflog, Sarah L.; Frey, Nathan C.; Yang, Wenlong; Dickie, Diane A.; Webster, Charles E.; Gilliard, Robert J. Chem.−Eur. J. 2020, 26, 10072-10082. 
DOI: 10.1002/chem.202002118

*Invited: Young Chemists Special Issue to Commemorate Emerging Scientists (Celebration of the 25th Anniversary)

33. Crystallographic Study of a Heteroleptic Chloroberyllium Borohydride Carbodicarbene Complex Walley, Jacob E.;  Dickie, Diane A.; Gilliard, Robert J. Z. Naturforsch. B 2020, 75, 495-501. DOI: 10.1515/znb-2020-0033
*Inivited: Themed Issue on Beryllium Chemistry

32. A Stable, Crystalline Beryllium Radical Cation Wang, Guocang; Walley, Jacob E.;  Dickie, Diane A.; Pan, Sudip; Frenking, Gernot; Gilliard, Robert J. J. Am. Chem. Soc. 2020, 142, 4560-4564. DOI: 10.1021/jacs.9b13777 
*Highlighted in Chemical & Engineering News
*Highlighted in Chemical & Engineering News - Molecules of the Year for 2020

31. Crystalline BP-Doped Phenanthryne via Photolysis of The Elusive Boraphosphaketene Yang, Wenlong; Krantz, Kelsie E.;  Dickie, Diane A.; Molino, Andrew; Wilson, David J. D.; Gilliard, Robert J. Angew. Chem. Int. Ed. 2020, 59, 3971-3975. DOI: 10.1002/anie.201916362

30. Persistent Borafluorene Radicals Yang, Wenlong; Krantz, Kelsie E.; Freeman, Lucas A.;  Dickie, Diane A.; Molino, Andrew; Frenking, Gernot; Pan, Sudip; Wilson, David J. D.; Gilliard, Robert J. Angew. Chem. Int. Ed. 2020, 59, 3850-3852. 
DOI: 10.1002/anie.201909627

29. Extremely Twisted and Bent Pyrene-Fused N-Heterocyclic Germylenes  Krantz, Kelsie E.; Weisflog, Sarah L.; Yang, Wenlong; Dickie, Diane A.; Frey, Nathan C.; Webster, Charles E.; Gilliard, Robert J. Chem. Commun. 2019, 55, 14954-14957. DOI: 10.1039/C9CC08703F

28. Low-Nuclearity Magnesium Hydride Complexes Stabilized by N-Heterocyclic Carbenes Freeman, Lucas A.; Walley, Jacob E.; Dickie, Diane A.; Gilliard, Robert J. Dalton Trans.2019, 48, 17174-17178. DOI: 10.1039/C9DT03915E

27. N-Heterocyclic Carbene-Supported Aryl- and Alk-oxides of Beryllium and Magnesium Walley, Jacob E.; Wong, Yuen Onn; Freeman, Lucas A.; Dickie, Diane A.; Gilliard, Robert J. Catalysts2019, 9, 934. †equal contribution DOI: 10.3390/catal9110934
*Invited: N‐Heterocyclic Carbenes and Their Complexes in Catalysis

26. Cyclic(Alkyl)(Amino) Carbene-Promoted Ring Expansion of a Carbodicarbene Beryllacycle Walley, Jacob E.; Obi, Akachukwu D.; Breiner, Grace; Wang, Guocang; Dickie, Diane A.; Molino, A.; Dutton, Jason L.; Wilson, David J. D.; Gilliard, Robert J. Inorg. Chem.2019, 58, 11118-11126. DOI: 10.1021/acs.inorgchem.9b01643.

25. Stable Borepinium and Borafluorenium Heterocycles: A Reversible Thermochromic "Switch" Based on Boron-Oxygen Interactions Yang, Wenlong; Krantz, Kelsie E.; Freeman, Lucas A.; Dickie, Diane A.; Molino, Andrew; Kaur, A.; Wilson, David J. D.; Gilliard, Robert J. Chem.−Eur. J. 2019, 25, 12512-12516. DOI: 10.1002/chem.201903348. *Hot Paper

24. Stepwise Reduction at Magnesium and Beryllium: Cooperative Effects of Carbenes with Redox Non-Innocent α-Diimines Freeman, Lucas A.; Walley, Jacob E.; Wang, Guocang; Obi, Akachukwu D.; Dickie, Diane A.; Molino, Andrew; Wilson, David J. D.; Gilliard, Robert J. Inorg. Chem.2019, 58, 10554-10568. DOI: 10.1021/acs.inorgchem.9b01058.
*Invited: Celebrating the Year of the Periodic Table: Emerging Investigators in Inorganic Chemistry

23. Metal-Free Electrochemical Reduction of Carbon Dioxide Mediated by Cyclic(Alkyl)(Amino) Carbenes Lipske, Lauren E.; Freeman, Lucas A.; Wang, Guocang; Dickie, Diane A.; Gilliard, Robert J.; Machan, Charles W. Chem.−Eur. J. 2019, 25, 6098-6101. DOI: 10.1002/chem.201900316. †equal contribution
*Top 10% Most Downloaded for 2019

22. Isolation of Cyclic(Alkyl)(Amino) Carbene-Bismuthinidene Mediated by a Beryllium(0) Complex Wang, Guocang; Freeman, Lucas A.; Dickie, Diane A.; Mokrai, Réka; Benkő, Zoltán; Gilliard, Robert J. Chem.−Eur. J. 2019, 25, 4335-4339. DOI: 10.1002/chem.201900458. 
*Special Collection: United Nations International Year of the Periodic Table
*Highlighted in ChemistryViews

21. s-Block Carbodicarbene Chemistry: C(sp3)−H Activation and Cyclization Mediated by a Beryllium Center Walley, Jacob E.; Breiner, Grace; Wang, Guocang; Dickie, Diane A.; Molino, Andrew; Dutton, Jason L.; Wilson, David J. D.; Gilliard, Robert J. Chem. Commun. 2019, 55, 1967-1970. DOI: 10.1039/C8CC10022E.

20. Two Carbenes Versus One in Magnesium Chemistry: Synthesis of Terminal Dihalide, Dialkyl, and Grignard Reagents Wong, Yuen Onn; Freeman, Lucas A.; Agakidou, A. Danai; Dickie, Diane; Webster, Charles E.; Gilliard, Robert J. Organometallics 2019, 38, 688-696. DOI: 10.1021/acs.organomet.8b00866. *Most Downloaded List (Jan/Feb 2019)

19. Highly Reactive Cyclic(Alkyl)(Amino) Carbene- and N-Heterocyclic Carbene-Bismuth(III) Complexes: Synthesis, Structure, and Computations Wang, Guocang; Freeman, Lucas A.; Dickie, Diane A.; Mokrai, Réka; Benkő, Zoltán; Gilliard, Robert J. Inorg. Chem. 2018, 57, 11687-11695. DOI: 10.1039/C8CC10022E *Most Downloaded List (Nov/Oct/Dec 2018)

Research Prior to the University of Virginia:

18. 18. Suter, Riccardo; Gilliard Jr., Robert J.; Zoltán Benkő, Grützmacher, Hansjörg “Anionic 1-Aza-3,4-Diphospholides as redox active ligands” Inorg. Chem. Acta. 2021 (accepted)

17. Gilliard Jr., Robert J.; Kieser, Jerod M.; Protasiewicz, John D.; “Synthons for the Development of New Organophosphorus Functional Materials” Main Group Strategies Towards Functional Hybrid Materials Wiley 2018.

16. Gilliard Jr., Robert J.; Heift, Dominikus; Benkő, Zoltán; Kieser, Jerod M.; Rheingold, Arnold; Grützmacher, Hansjörg; Protasiewicz, John D. "An Isolable Magnesium Diphosphaethynolate Complex" Dalton Trans. 201847, 666-669.

15. Gilliard Jr., Robert J.; Suter, Riccardo; Schrader, Erik; Benkő, Zoltán; Rheingold, Arnold; Grützmacher, Hansjörg; Protasiewicz, John D. “Synthesis of P2C2O2 and P2CO via NHC-Mediated Coupling of the Phosphaethynolate Anion” Chem. Commun. 2017, 53, 12325-12328..

14. Kieser, Jerod M.; Gilliard Jr., Robert J.; Rheingold, Arnold; Grützmacher, Hansjörg, Protasiewicz, John D.; “Insertion of Sodium Phosphaethynolate, Na[OCP], into a Zirconium-Benzyne Complex” Chem. Commun. 2017, 53, 5110-5112.

13. Beil, Andreas; Gilliard Jr., Robert J.; Grützmacher, Hansjörg “From the Parent Phosphinidene-Carbene Adduct NHC=PH to Cationic P4-Rings and P2-Cycloaddition Products” Dalton Trans. 2016, 45, 2044-2052.

12. Chen, Mingwei; Wang, Yuzhong; Yaoming, Xie; Wei, Pingrong; Gilliard Jr., Robert J.; Schwartz, Nichole A.; Schaefer III, Henry F.; Schleyer, Paul v. R.; Robinson, Gregory H. “Dynamic Complexation of Copper(I) Chloride by Carbene-Stabilized DisiliconChem. Eur. J. 2014, 20, 9208-9211.

11. Chen, Mingwei; Wang, Yuzhong; Gilliard Jr., Robert J.; Wei, Pingrong; Schwartz, Nichole A.; Robinson, Gregory H. “Synthesis and Molecular Structure of an Abnormal Carbene Gallium Chloride ComplexDalton Trans. 2014, 43, 14211-14214.

10. Wang, Yuzhong; Abraham, Mariham Y.; Gilliard Jr., Robert J.; Sexton, Daniel R.; Wei, Pingrong; Robinson, Gregory H. “N-Heterocyclic Olefin-Stabilized Borenium CationsOrganometallics 2013, 32, 6639-6642.

9. Abraham, Mariham Y.; Wang, Yuzhong; Yaoming, Xie; Gilliard Jr., Robert J.; Wei, Pingrong; Vaccaro, Brian J.; Johnson, Michael K.; Schaefer III, Henry F.; Schleyer, Paul v. R.; Robinson, Gregory H. “Oxidation of Carbene-Stabilized Diarsenic: Diarsene Dications and Diarsenic Radical CationsJ. Am. Chem. Soc. 2013, 135, 2486-2488.

8. Wang, Yuzhong; Yaoming, Xie; Abraham, Mariham Y.; Gilliard Jr., Robert J.; Wei, Pingrong; Schaefer III, Henry F.; Schleyer, Paul v. R.; Robinson, Gregory H. “NHC-Stabilized Triorganozincates: Syntheses, Structures, and Transformation to Abnormal Carbene-Zinc ComplexesAngew. Chem., Int. Ed. 2012, 51, 10173-10176.

7. Gilliard Jr., Robert J.; Abraham, Mariham Y.; Wang, Yuzhong; Wei, Pingrong; Yaoming, Xie; Quillian, Brandon; Schaefer III, Henry F.; Schleyer, Paul v. R.; Robinson, Gregory H. “Carbene-Stabilized Beryllium BorohydrideJ. Am. Chem. Soc. 2012, 134, 9953-9955.

6. Wang, Yuzhong; Yaoming, Xie; Abraham, Mariham Y.; Gilliard Jr., Robert J.; Wei, Pingrong; Smith, Jared C.; Robinson, Gregory H. “From Anionic Dicarbenes to Abnormal Carbene-Borane ComplexesOrganometallics 2012, 131, 791-793.

5. Wang, Yuzhong; Yaoming, Xie; Abraham, Mariham Y.; Gilliard Jr., Robert J.; Wei, Pingrong; Schaefer III, Henry F.; Schleyer, Paul v. R.; Robinson, Gregory H. “Carbene-Stabilized Parent PhosphinideneOrganometallics 2010, 132, 14370-14372.

4. Malgalum, Anshuman; Gilliard Jr., Robert J.; Hanley, Jessica M.; Parker, Austa M.; Smith, Rhett C. “Metal Ion Detection by Luminescent 1,3-bis(dimethylamino)xylyl Receptor-Modified Chromophores and CruciformsOrg. Biomol. Chem. 2010, 8, 5620-5627.

3. Morgan, Brad P., Gilliard Jr., Robert J.; Loungani, Rahul S.; Smith, Rhett C. “Poly(p-phenylene ethylene) Incorporating Sterically Enshrouding m-Terphenyl Oxycyclophane CanopiesMacromol. Rapid Commun. 2009, 30, 1399-1405. *Cover Article

2. Morgan, Brad P.; Galdamez, Gabriela A.; Gilliard Jr., Robert J.; Smith, Rhett C. “Canopied trans-chelating Bis(N-heterocyclic Carbene) Ligand: Synthesis, Structure and CatalysisDalton Trans. 2009, 11, 2020-2028.

1. Gilliard Jr., Robert J.; Iacono, Scott T.; Buddy, Stephen M.; Moody, Justin D.; Smith Jr.,  Dennis W.; Smith, Rhett C. “Chromophore-Derivatized Semifluorinated Polymers for Colorimetric and Turn-On Fluorescent Anion DetectionSens. Actuators B. 2009, 143, 1-5.