Agapie Group Inorganic, Organometallic and Bioinorganic Chemistry
Synthesis, Mechanism and Catalysis

collage of research photos

Our research focuses on developing molecular solutions to problems related to energy, materials, and health. Having nature as a source of inspiration, we develop and study systems displaying interactions between multiple molecular centers (metals, Lewis acids, hydrogen bonding functionalities, etc.) to facilitate a variety of chemical processes.

From a small molecule perspective, we target systems able to perform transformations important in organic methodology, new materials generation as well as in the context of the energy economy. Areas of interest include selective C-H bond functionalization, polymerization of polar monomers, and multielectron processes such as water oxidation to dioxygen and dinitrogen fixation. To attain these goals we design and synthesize ligand frameworks that allow for the binding of several metals in close proximity. Hydrogen bonding networks and pendant Lewis acids are built in if believed to be important for the desired transformations. The synthesized multimetallic complexes are studied using a variety of spectroscopic tools to understand their electronic structure and its effects on reactivity. The lessons learned from these studies will be used to ultimately develop molecular catalysts for chemical processes of importance in today's world.

In a biochemical context, we study interactions and transformations involving bioinorganic molecules. One topic of interest regards the properties and reactivity of protein-embedded clusters. Metal clusters perform a variety of biological functions, ranging from electron transfer and signaling to catalysis of complex transformations. Our initial focus is on the biochemistry of iron-sulfur clusters. Proteins displaying iron-sulfur clusters are expressed in high yields to allow for active site engineering and reactivity studies. These studies will improve our understanding of the strategies evolved by Nature to facilitate chemical transformations using metal clusters. One potential application will be the design of biocatalysts for the generation of fuels from water or carbon dioxide.

Papers

40)Kyle T. Horak, Alexandra Velian, Michael W. Day, and Theodor Agapie “Arene Non-Innocence in Dinuclear Complexes of Fe, Co, and Ni Supported by a para-Terphenyl Diphosphine” Chem. Commun., 2014, 50, 4427-4429. link
39)David E. Herbert, Davide Lionetti, Jonathan Rittle, and Theodor Agapie “Heterometallic Triiron-Oxo/Hydroxo Clusters: Effect of Redox-Inactive Metals” J. Am. Chem. Soc., 2013, 135, 19075-19078. link
38)Emily Y. Tsui, Jacob S. Kanady, and Theodor Agapie “Synthetic Cluster Models of Biological and Heterogeneous Manganese Catalysts for O2 Evolution” Inorg. Chem., 2013, 52, 13833-13848 link (Award Paper also featured on the cover)
37)Sandy Suseno, Kyle T. Horak, Michael W. Day, and Theodor Agapie “Trinuclear Nickel Complexes with Metal–Arene Interactions Supported by Tris- and Bis(phosphinoaryl)benzene Frameworks” Organometallics, 2013, 32, 6883-6886 link
36)Sibo Lin, David E. Herbert, Alexandra Velian, Michael W. Day, and Theodor Agapie “Dipalladium(II) Terphenyl Diphosphine Complexes as Models for Two-Site Adsorption and Activation of Organic Molecules” J. Am. Chem. Soc., 2013, 135, 15830-15840 link
35)David E. Herbert, Nadia C. Lara, Theodor Agapie “Arene C-H Amination at Nickel Terphenyl-Diphosphine Complexes with Labile Metal-Arene Interactions” Chem. Eur. J., 2013, 19, 16453-16460 link
34)Jacob S. Kanady, Rosalie Tran, Jamie A. Stull, Luo Lu, Troy A. Stich, Michael W. Day, Junko Yano, David R. Britt, and Theodor Agapie “Role of Oxido Incorporation and Ligand Lability in Exapanding Redox Accessibility of Structurally Related Mn4 Clusters” Chem. Sci., 2013, 4, 3986-3996 link
33)Sandy Suseno and Theodor Agapie “Intramolecular Arene C-H to C-P Functionalization by Nickel(II) and Palladium(II)” Organometallics, 2013, 32, 3161-3164 link
32)Paul Kelley, Michael W. Day, and Theodor Agapie “Hydrogen Evolution Catalyzed by Aluminum-Bridged Cobalt Diglyoximate Complexes” Eur. J. Inorg. Chem., 2013, 3840-3845 link (special issue on small-molecule activation by reactive metal complexes; article featured on the cover with cover profile)
31)Emily Y. Tsui and Theodor Agapie “Reduction Potentials of Heterometallic Manganese-Oxido Cubane Complexes Modulated by Redox-Inactive Metals” Proc. Natl. Acad. Sci. U.S.A., 2013, 110, 10084-10088 link
30)Madalyn R. Radlauer, Aya K. Buckley, Lawrence M. Henling, and Theodor Agapie “Bimetallic Coordination Insertion Polymerization of Unprotected Polar Monomers: Copolymerization of Amino Olefins and Ethylene by Dinickel Bisphenoxyiminato Catalysts” J. Am. Chem. Soc., 2013, 135, 3784-3787 link
29) Emily Y. Tsui, Rosalie Tran, Junko Yano, and Theodor Agapie “Redox-inactive metals modulate the reduction potential in heterometallic manganese—oxido clusters” Nature Chem., 2013, 5, 293-299 link (commentaries in Nature Chemistry and Caltech News)
28)Jacob S. Kanady, Jose L. Mendoza-Cortes, Emily Y. Tsui, Robert J. Nielsen, William A. Goddard, III, and Theodor Agapie “Oxygen Atom Transfer and Oxidative Water Incorporation in Cuboidal Mn3MOn Complexes Based on Synthetic, Isotopic Labeling, and Computational Studies” J. Am. Chem. Soc., 2013, 135, 1073-1082 link
27)Davide Lionetti, Michael W. Day, and Theodor Agapie “Metal-Templated Ligand Architectures for Trinuclear Chemistry: Tricopper Complexes and Their O2 Reactivity” Chem. Sci., 2013, 4, 785-790 link
26)Paul Kelley, Madalyn R. Radlauer, Abraham J. Yanez, Michael W. Day, and Theodor Agapie “Metallomacrocycles as ligands: synthesis and characterisation of aluminium-bridged bisglyoximato complexes of palladium and iron” Dalton Trans., 2012, 41, 8086-8092 (Young Talent Issue) link
25)Paul Kelley, Sibo Lin, Guy Edouard, Michael W. Day, and Theodor Agapie “Nickel-Mediated Hydrogenolysis of C—O Bonds of Aryl Ethers: What Is the Source of the Hydrogen?” J. Am. Chem. Soc., 2012, 134, 5480-5483 link
24)Madalyn R. Radlauer, Michael W. Day, and Theodor Agapie “Dinickel Bisphenoxyiminato Complexes for the Polymerization of Ethylene and α-Olefins” Organometallics, 2012, 31, 2231-2243 link
23)Madalyn R. Radlauer, Michael W. Day, and Theodor Agapie “Bimetallic Effects on Ethylene Polymerization in the Presence of Amines: Inhibition of the Deactivation by Lewis Bases” J. Am. Chem. Soc., 2012, 134, 1478-1481 link
22)Charlotte A. Whited, Jeffrey J. Warren, Katherine D. Lavoie, Emily E. Weiner, Theodor Agapie, Jay R. Winkler, and Harry B. Gray “Gating NO Release from Nitric Oxide Synthase” J. Am. Chem. Soc., 2012, 134, 27-30 link
21)Jacob S. Kanady, Emily Y. Tsui, Michael W. Day, and Theodor Agapie “A Synthetic Model of the Mn3Ca Subsite of the Oxygen-Evolving Complex in Photosystem II” Science, 2011, 333, 733-736 link (commentaries in Chemical & Engineering News, Chemistry World, and Education in Chemistry)
20)Steven T. Chao, Nadia C. Lara, Sibo Lin, Michael W. Day and Theodor Agapie “Reversible Halide-Modulated Nickel–Nickel Bond Cleavage: Metal–Metal Bonds as Design Elements for Molecular Devices” Angew. Chem. Int. Ed., 2011, 50, 7529–7532 link
19)Emily Y. Tsui, Jacob S. Kanady, Michael W. Day, and Theodor Agapie “Trinuclear First Row Transition Metal Complexes of a Hexapyridyl, Trialkoxy 1,3,5-Triarylbenzene Ligand” Chem. Commun., 2011, 47, 4189-4191 link
18)Sibo Lin, Michael W. Day, and Theodor Agapie “Nickel Hydrides Supported by a Non-Innocent Diphosphine Arene Pincer: Mechanistic Studies of Nickel−Arene H-Migration and Partial Arene Hydrogenation” J. Am. Chem. Soc., 2011, 133, 3828-3831 link
17)Emily Y. Tsui, Michael W. Day, and Theodor Agapie “Trinucleating Copper: Synthesis and Magnetostructural Characterization of Complexes Supported by a Hexapyridyl 1,3,5-Triarylbenzene Ligand” Angew. Chem. Int. Ed., 2011, 50, 1668-1672 link
16)Theodor Agapie “Selective Ethylene Oligomerization: Recent Advances in Chromium Catalysis and Mechanistic Investigations” Coord. Chem. Rev., 2011, 255, 861-880 link
15)Sibo Lin and Theodor Agapie “Cross-Coupling Chemistry at Mononuclear and Dinuclear Nickel Complexes” Synlett, 2011, 1, 1-5 link
14)Alexandra Velian, Sibo Lin, Alexander J. M. Miller, Michael W. Day and Theodor Agapie “Synthesis and C–C Coupling Reactivity of a Dinuclear NiI–NiI Complex Supported by a Terphenyl Diphosphine” J. Am. Chem. Soc., 2010, 132 (18), 6296-6297 link
Undergraduate, Graduate, and Post-Doctoral Work ↓
13)Ian A. Tonks, Daniel Tofan, Edward C. Weintrob, Theodor Agapie, and John E. Bercaw “Zirconium and Titanium Propylene Polymerization Precatalysts Supported by a Fluxional C2-Symmetric Bis(anilide)pyridine Ligand” Organometallics, 2012, 31 1965-1974 link
12)Theodor Agapie, Sandy Suseno, Joshua J. Woodward, Stefan Stoll, R. David Britt, and Michael A. Marletta “NO formation by a catalytically self-sufficient bacterial nitric oxide synthase from Sorangium cellulosumsProc. Natl. Acad. Sci. USA 2009, 106 (38), 16221-16226 link
11)Theodor Agapie, Michael W. Day, and John E. Bercaw “Synthesis and Reactivity of Tantalum Complexes Supported by Bidentate X2 and Tridentate LX2 Ligands having Two Phenolates Linked to Pyridine, Thiophene, Furan, and Benzene Connectors – Mechanistic Studies of the Formation of a Tantalum Benzylidene and Insertion Chemistry for Tantalum Carbon Bonds” Organometallics 2008, 27 (23), 6123-6142 link
10)Theodor Agapie, Lawrence M. Henling, Antonio G. DiPasquale, Arnold L. Rheingold, and John E. Bercaw “Zirconium and Titanium Complexes Supported by Tridentate LX2 Ligands having Two Phenolates Linked to Furan, Thiophene, and Pyridine Donors: Precatalysts for Propylene Polymerization and Oligomerization” Organometallics 2008, 27 (23), 6245-6256 link
9)Theodor Agapie, Jay A. Labinger, and John E. Bercaw “Mechanistic Studies of Olefin Trimerization with Chromium Catalysts – Deuterium Labeling and Studies of Regiochemistry Using a Model Cromacyclopentane Complex” J. Am. Chem. Soc. 2007, 129 (46), 14281-14295 link 
8)Theodor Agapie and John E. Bercaw “Cyclometallated Tantalum Diphenolate Pincer Complexes: Intramolecular C-H/M-CH3 σ– Bond Metathesis May Be Faster than O-H/M-CH3 Protonolysis" Organometallics 2007, 26 (12), 2957-2959 link
7)Smaranda C. Marinescu, Theodor Agapie, Michael W. Day, and John E. Bercaw "Group 3 Dialkyl Complexes with Tetradentate (L, L, N, O; L = N, O, S) Monoanionic Ligands – Synthesis and Reactivity" Organometallics 2007, 26 (5), 1178-1190 link 
6)Theodor Agapie, Michael W. Day, Lawrence M. Henling, Jay A. Labinger, and John E. Bercaw “A Chromium Diphosphine System for Catalytic Ethylene Trimerization: Synthetic and Structural Studies of Chromium Complexes with a Nitrogen-Bridged Diphosphine Ligand with ortho-Methoxyaryl Substituents” Organometallics 2006, 25 (11), 2733-2742 link 
5)Theodor Agapie, Susan J. Schofer, Jay A. Labinger, and John E. Bercaw “Mechanistic Studies of the Ethylene Trimerization Reaction with Chromium – Diphosphine Catalysts: Experimental Evidence for a Mechanism Involving Metallacyclic Intermediates” J. Am. Chem. Soc. 2004, 126 (5), 1304-1305 link 
4)Theodor Agapie, Paula L. Diaconescu, and Christopher C. Cummins “Methine (CH) Transfer via a Chlorine Atom Abstraction/Benzene-Elimination Strategy: Molybdenum Methylidyne Synthesis and Elaboration to a Phosphaisocyanide Complex” J. Am. Chem. Soc. 2002, 124 (11), 2412-2413 link 
3)Theodor Agapie, Paula L. Diaconescu, Daniel J. Mindiola and Christopher C. Cummins “Radical Scission of Symmetrical 1,4-Dicarbonyl Compounds: C-C Bond Cleavage with Titanium(IV) Enolate Formation and Related Reactions” Organometallics 2002, 21 (7), 1329-1340 link 
2)Paula L. Diaconescu, Aaron L. Odom, Theodor Agapie and Christopher C. Cummins “Uranium-Group 14 Element Single Bonds: Isolation and Characterization of a Uranium(IV) Silyl Species” Organometallics 2001, 20 (24), 4993-4995 link 
1)Theodor Agapie, Aaron L. Odom, Christopher C. Cummins “In Pursuit of the Molybdenum(III) Tris(thiolate) Fragment: Unusual Structure of a Dimolybdenum μ -Nitrido Complex" Inorg. Chem. 2000, 39 (2), 174-179 link

Patents

2)Madalyn Radlauer, Joshua D. Wiensch, Aya K. Buckley, and Theodor Agapie "Multi-metallic organometallic complexes, and related polymers, compositions, methods and systems" Patent Application 20130066029.
1)Theodor Agapie, Suzanne R. Golisz, Daniel Tofan, and John E. Bercaw "Non-metallocene organometallic complexes and related methods and systems" Patent US007847099.

Ch102 (S'09, S'10, S'11, S'12, S'13, Spring 2014)

Intro to Inorganic Chemistry

Syllabus

Problem Sets
Problem Set 1
Problem Set 1 Answer Key
Problem Set 2

Supplemental Material
Sample Presentation

Ch212a (Spring 2010, Spring 2012)

Bioinorganic Chemistry

Course website

Ch5b (F'10, F'11, F'12, Fall 2013)

Advanced Techniques of Synthesis and Analysis

Coordination and Organometallic Compounds

Course Manual
Development of Techniques for Handling Organometallic Compounds
Swivel Frit Operation (video by Jeff Byers)
Short Report Rubric
Short Report Template (.docx)
Long Report Rubric
Theo Office: 314 Noyes
Laboratory: 301-309 Noyes
Phone: 626-395-3617
E-mail (at caltech.edu): agapie

Administrative Assistant: Margarita Davis
Office: Noyes 134
Phone: 626-395-6856
E-mail: davism@caltech.edu

Mailing address:
Department of Chemistry, MC 127-72
1200 East California Boulevard
California Institute of Technology
Pasadena, CA 91125

Theodor Agapie was born in 1979 in Bucharest, Romania. He received his B.S. degree from Massachusetts Institute of Technology in 2001 and his Ph.D. from California Institute of Technology in 2007. Upon completion of his Ph.D. he moved to University of California, Berkeley as a Miller Postdoctoral Fellow.

Theo developed his passion for chemistry during high school and participated in chemistry competitions; he won two silver medals at the International Chemistry Olympiads as part of the Romanian team. While an undergraduate at MIT, he worked with Professor Christopher C. Cummins for more that three and a half years on atom and fragment transfer chemistry involving metal complexes, on titanium-ketyl radical chemistry, and on DFT computations to detail the electronic structure of synthesized complexes. At graduation, he received the Chemistry Department's Alpha Chi Sigma Award for achievement in research, scholarship, and service to the department. At Caltech, Theo worked under the tutelage of Professor John E. Bercaw on mechanistic and synthetic aspects of chromium-based olefin oligomerization catalysis and on developing new early transition metal nonmetallocene olefin polymerization catalysts. His Ph.D. thesis received Caltech's Chemistry Department Herbert Newby McCoy Award for outstanding contribution to the science of chemistry. Upon graduation, in May 2007, Theo moved to UC Berkeley to work with Professor Michael A. Marletta as a Miller Institute Fellow. There, he focused on mechanistic aspects of biochemical nitric oxide synthesis involving the metalloprotein nitric oxide synthase.

Theo returned to Caltech on February 11, 2009 to start his independent career as an assistant professor of chemistry. Selected awards include the Searle Award (2010), Sloan Fellowship (2012), NSF CAREER Award (2012), and ACS Award in Pure Chemistry (2013).

Post-Doctoral Scholar

Po-HengPo-Heng Lin
University of Ottawa Ph.D. '12
National Tsing Hua University M.S. '04
National Chung Cheng University B.S. '02
poheng80

Graduate Students

JoshJoshua Buss
Claremont McKenna College '12
B.A. Chemistry
jbuss
GuyGuy Edouard
Harvard College '10
B.A. Chemical and Physical Biology
gedouard
JustinJustin Henthorn
Ohio University '10
B.S. Chemistry
B.A. Economics
jhenthor
KyleKyle Horak
Cornell University'10
B.A. Chemistry
khorak
JacobJacob Kanady
UC Irvine '09
B.S. Chemistry
jkanady
PaulPaul Kelley
Catholic University of America '08
B.S. Biochemistry
egadsman
DavideDavide Lionetti
University of Notre Dame '09
B.S. Chemistry
dlionett
SandySandy Suseno
UC Berkeley '08
B.S. Chemical Biology
ssuseno
EmilyEmily Tsui
MIT '08
S.B. Chemistry
etsui

Post-Doctoral Alumnus

DaveDave E. Herbert
University of Bristol Ph.D. '10
University of Toronto M.Sc. '06
University of King's College B.Sc. '04

Assistant Professor - University of Manitoba
Herbert Group Website

Graduate Alumni

StevenSteven Chao
M.S. Caltech '11
University of Texas '08
B.S. Chemistry
stchao
SiboSibo Lin
Ph.D. Caltech '14
Indiana University '08
B.S. Chemistry
sibolin
MaddyMadalyn Radlauer
Ph.D. Caltech '14
Stanford University '08
B.S. Chemistry
madalyn

Undergraduate Alumni

MartinMartin Bernat
University College London '10
mbernat
AyaAya Buckley
Columbia '13
Chun-SunChung-Sun Chen
Cambridge '13
ChristineChristine Cheng
Caltech '14
ccheng
MichaelMichael Desanker
MIT '13
mdesanke
JenJennifer Karolewski
Caltech '15
jkarolews
NadiaNadia Lara
Caltech '12
lara
JudyJudy Mou
Caltech '13
xmou
EvaEva Nichols
Caltech '12
eva
Wei JianWei Jian Ong
Caltech '13
ong
JadeJade Shi
Caltech '12
jadeshi
AlexAlexandra Velian
Caltech '09
velian
AndreasAndreas Wierschen
University of North Carolina '11
awiersch
AbrahamAbraham Yanez-McKay
Michigan State University '11
----
VictorYuanchi "Victor" Zhao
Yale University '13
yzzhao

Group Photos

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Kearsarge Pass Trip August 2013

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Mono Pass Trip August 2012

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Palisade Glacier Trip August 2011

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Bishop Pass Trip August 2010

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Mono Pass Trip August 2009

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Huntington Beach BBQ July 2009

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Lab Initiation February 2009

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High School Outreach May 2013

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High School Outreach May 2012

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Summer Chemistry Workshop August 2011

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Introduction.pdf
ClockReaction_InitialRates_Student.pdf
ClockReaction_InitialRates_Teacher.pdf
ClockReaction_IntegratedRateLaws_Student.pdf
ClockReaction_IntegratedRateLaws_Teacher.pdf
Data_Plots.xls

High School Outreach May 2011

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High School Outreach May 2010

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Calendar

Agenda