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Rick Geier

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Rick Geier

Warren 鈥43 and Lillian Anderson Chair in Chemistry; Director, Division of Natural Sciences and Mathematics

Department/Office Information

Chemistry
201 Wynn Hall
  • T 3:30pm - 4:30pm (201 Wynn Hall)
  • W 11:00am - 12:00pm (201 Wynn Hall)
  • R 1:30pm - 2:30pm (201 Wynn Hall)
  • F 10:15am - 11:15am (201 Wynn Hall)

Contact

(315) 228-6795

BA听(Chemistry and Biology),听Luther College, 1992; Ph.D (Chemistry),听University of Washington, 1997

  • Director, Division of Natural Sciences and Mathematics, 2022-present
  • Department Chair, P站视频, 2019-2022
  • Warren 鈥43 and Lillian Anderson Chair in Chemistry, P站视频, 2018-present
  • Professor, P站视频, 2014-present
  • Department Chair, P站视频, 2010-2013
  • Associate Professor, P站视频, 2006-2014
  • Visiting Scholar, Rensselaer Polytechnic Institute, 2004
  • Assistant Professor, P站视频, 2000-2006
  • Research Assistant Professor, North Carolina State University, 1999-2000
  • Postdoctoral Research Associate, North Carolina State University, 1997-1999

Organic chemistry

CHEM 101/102:听General Chemistry I and II
CHEM 263/264:听Organic Chemistry I and II
CHEM 381:听Practical Quantitative Analysis
CHEM 461:听Organic Reaction Mechanisms
CHEM 464:听Organic Synthesis
CHEM 468:听Medicinal Chemistry
CORE 105:听Science and Implications of Nanotechnology

Studies of porphyrinoid synthetic methodology and porphyrinoid properties

Research in the Geier laboratory is directed towards investigation of methods for the preparation of a variety of porphyrinoids. Successful syntheses facilitate studies of porphyrinoid properties such as stability, spectroscopy, metal binding, and catalysis.

Porphyrins perform diverse functions in Nature (Figure 1). For example, the characteristic red color of blood and green color of plants are due to porphyrinoids (heme and chlorophyll, respectively). The rich array of porphyrin function arises from the variety of ways in which 听macrocycle properties can be fine-tuned. The identity of the central metal ion and axial ligands are important. The protein matrix surrounding the porphyrin ring also influences macrocycle properties. And of particular interest to our research group, the core structure of the porphyrin can be substituted, reduced, heteroatom modified, isomerized, expanded, and/or contracted relative the prototypical porphyrin structure.

Figure 1

Structural alterations to the porphyrin macrocycle gives rise to a large family of molecules that display a wide range of complementary properties (Figure 2). Some of the general structures shown in Figure 2 are found in Nature. Others have been created in the laboratory in an effort to produce porphyrinoids of fundamental interest, and materials useful for a wide range of commercial applications including molecular electronic devices, solar energy, photodynamic cancer therapy, ion selective sensors, and catalysis.

Figure 2

In the Geier research group, we have a number of ongoing projects involving many of the porphyrinoids shown in Figure 2. Presently, we are exploring the series of compounds shown in Figure 3. The central core of the porphyrinoids differ in subtle, but profound ways which impact metal binding and properties of the metal chelates. To forward these efforts, our group has contributed methodology for the preparation of corroles (J. Org. Chem.听2004,听69, 4159-4169), phlorin (J. Org. Chem.听2007,听72, 4084-4092;听J. Org. Chem.听2016,听81, 5021-5031), and 5-isocorrole (J. Org. Chem.听2010,听75, 553-563).听 Recently, we reported a streamlined, one-flask synthesis of an N-confused porphyrin bearing pentafluorophenyl substituents (J. Org. Chem.听2017,听82, 4429-4434). The phlorins prepared by our group are noteworthy as they are among the most stable phlorins known towards degradation in light and air. Metal coordination of a 5-isocorrole has been investigated in collaboration with the Ziegler group at The University of Akron (Dalton Trans.听2011,听40, 4384-4386). Magnetic circular dichroism studies have been performed on transition-metal complexes of the perfluorophenyl-N-confused porphyrin in collaboration with the Nemykin (University of Manitoba) and Ziegler groups (J. Phys. Chem. A.2017,听121, 3689-3698). Further studies of the coordination chemistry of these porphyrinoids are ongoing. We also continue to target additional novel porphyrinoids in our synthetic investigations.

Figure 3

We utilize a broad range of experimental techniques in our work including preparative organic synthesis and purification methods (extraction, distillation, sublimation, chromatography, and crystallization), parallel analytical-scale reactions, analytical chromatographic methods (GC and HPLC), and a variety of spectroscopic tools (NMR, UV-vis, IR, EI-MS, and LD-MS).

Please make an appointment with Professor Geier to discuss current research opportunities in the Geier laboratory.

Further Readings

Excellent reviews of many topics germane to this research may be found in听The Porphyrin Handbook, Kadish, K.M.; Smith, K.M.; Guilard, R., eds. Academic Press,听2000;听and in听The Colours of Life,听Milgrom, L. R., Oxford University Press: New York,听1997.

External Funding听(PI):听American Chemical Society Petroleum Research Fund, Type G, 2002-2005;听Research Corporation, Cottrell College Science Awards, 2002-2005;听National Science Foundation, Course, Curriculum, and Laboratory Improvement-Adaptation and Implementation, 2003-2006;听National Science Foundation Research at Undergraduate Institutions, 2005-2008.听National Science Foundation Major Research Instrumentation, 2021-2024.

External Funding (Co-PI):听听National Science Foundation, Course, Curriculum, and Laboratory Improvement-Adaptation and Implementation, 2001-2003;听National Science Foundation Major Research Instrumentation, 2008-2011; National Science Foundation Major Research Instrumentation, 2017-2020.

  • Doble, S.; Osinski, A. J.; *Holland, S. M.; *Fisher, J. M.; Geier, G. R., III; Belosludov, R.V.; Ziegler, C. J.; Nemykin, V. N. 鈥淢agnetic Circular Dichroism of Transition-Metal Complexes of Perfluorophenyl-N-Confused Porphyrins: Inverting Electronic Structure through a Proton,鈥澨J. Phys. Chem. A.听2017,听121, 3689-3698.
  • *Fisher, J. M.; *Kensy, V. K.; Geier, G. R., III 鈥淭wo-Step, One-Flask Synthesis of an N-Confused Porphyrin Bearing Pentafluorophenyl Substituents,鈥澨J. Org. Chem.听2017,听82, 4429-4434.
  • Kim, D.; *Chun, H.-J.; *Donnelly, C. C.; Geier, G. R., III听鈥淭wo-Step, One-Flask Synthesis of a Meso-Substituted Phlorin,鈥澨J. Org. Chem.听2016,听81, 5021-5031.
  • Rhoda, H. M.;听Crandall, L. A.;听Geier, G. R., III;听Ziegler, C. J.; Nemykin, V. N.听鈥淐ombined MCD/DFT/TDDFT Study of the Electronic Structure of Axially Pyridine Coordinated Metallocorroles,鈥澨Inorg. Chem.听2015,听54, 4652鈥4662.
  • *Bruce, A. M.; *Weyburne, E. S.; Engle, J. T.; Ziegler, C. J.; Geier, G. R., III听鈥淧hlorins Bearing Different Substituents at the sp3-Hybridized Meso-Position,鈥澨J. Org. Chem.听2014,听79, 5664-5672.
  • Ziegler, C. J.; Sabin, J. R.; Geier, G. R., III; Nemykin, V. N. 鈥淭he First TDDFT and MCD Studies of Free Base Triarylcorroles: A Closer Look into Solvent-Dependent UV-visible Absorption,鈥澨Chem. Commun.,听2012,听48, 4743-4745.
  • Costa, R.; Geier, G. R., III; Ziegler, C. J. 鈥淪tructure and Spectroscopic Characterization of Free Base and Metal Complexes of 5,5-Dimethyl-10,15-bis(pentafluorophenyl)isocorrole,鈥澨Dalton Trans.,听2011,听40, 4384-4386.
  • *Flint, D. L.;听*Fowler, R. L.;听*LeSaulnier, T. D.;听*Long, A. C.;听O鈥橞rien, A. Y.; Geier, G. R., III 鈥淚nvestigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole,鈥澨J. Org. Chem.,听2010,听75, 553-563.
  • *Braaten, K. C.;听*Gordon, D. G.;听*Aphibal, M. M.;听Geier, G. R., III 鈥淓ffect of Carbinol Group Placement on Complementary Reactions of Dipyrromethane + Bipyrrole Species Leading to Corrole and/or an Octaphyrin,鈥澨Tetrahedron,听2008,听64, 9828-9836.
  • O鈥橞rien, A. Y.; *McGann, J. P.;听Geier, G. R., III 鈥淒ipyrromethane + Dipyrromethanedicarbinol Routes to an Electron Deficient meso-Substituted Phlorin with Enhanced Stability,鈥澨J. Org. Chem.,听2007,听72, 4084-4092.
  • *LeSaulnier, T. D.;听*Graham, B. W.;听Geier, G. R., III 鈥淓nhancement of Phlorin Stability by the Incorporation of meso-Mesityl Substituents,鈥澨Tetrahedron Lett.,听2005,听46, 5633-5637.
  • Geier, G. R., III; *Grindrod, S. C.听鈥淢eso-Substituted [34]Octaphyrin(1.1.1.0.1.1.1.0) and Corrole Formation in Reactions of a Dipyrromethanedicarbinol with 2,2'-Bipyrrole,鈥澨J. Org. Chem.,听2004,听69, 6404-6412.
  • Geier, G. R, III;听*Chick, J. F. B;听*Callinan, J. B.;听*Reid, C. G.;听*Auguscinski, W. P.听鈥淎 Survey of Acid Catalysis and Oxidation Conditions in the Two-Step, One-Flask Synthesis of meso-Substituted Corroles via Dipyrromethane-Dicarbinols and Pyrrole,鈥J. Org. Chem.,听2004,听69, 4159-4169.
  • Chevalier, F.; Geier, G. R., III; Lindsey, J. S. 鈥淎cidolysis of Intermediates Used in the Preparation of Core-Modified Porphyrinic Macrocycles,鈥澨J. Porphyrins Phthalocyanines,听2002,听6, 186-197.
  • Geier, G. R., III; *Callinan, J. B.;听Rao, D. P.; Lindsey, J. S. 鈥淎 Survey of Acid Catalysts in Dipyrromethanecarbinol Condensations Leading to听meso-Substituted Porphyrins,鈥澨J. Porphyrins Phthalocyanines,听2001,听5, 810-823.

Asterisks indicate undergraduate student co-authors who conducted their research in collaboration with a faculty member at Colgate.

The Preparation of a Metalloporphyrin-Peptide Conjugate Artificial Protein for the Catalytic Oxidation of Alkenes