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Miguel Garcia-Garibay, Ph.D.

Chair, Chemistry and Biochemistry
Chair, Organic Chemistry
Lab Director, Garcia-Garibay Lab
Professor, Chemistry and Biochemistry
Member, NanoMechanical and Nanofluidic Systems, California NanoSystems Institute
Researcher, Nanoscience and Materials, Organic, Synthesis

Ph.D., University of British Columbia, 1988

Academic Experience:
University of British Columbia, Fellowship for Undergraduate Research
UCLA, University Graduate Fellowship

Honors and Awards:
1999 UCLA, Herbert Newby McCoy Award
1997 UCLA, Dean's Marshal Award for the Dvision of Physical Sciences
1996 NSF, Career Award
1995 UCLA, Faculty Development Award

Professional Societies:
The Inter American Photochemical Society;
The American Chemical Society;
2008 - Elected to The American Association for the Advancement of Science (2008);

Contact Information:
Email Address:
Work Email Address:
Laboratory Address: Mol Sci Bldg 4235
Work Address: Mol Sci Bldg 4505C
Home Page:
Home Page:
ARR Papers:
Work Phone Number: 1 (310) 825-3159 Office
Lab Number: 1 (310) 206-1275 Lab
Additional Information:

Prof. Garcia-Garibay has been a Faculty member in the Department of Chemistry and Biochemistry since 1992. He came to UCLA after doing Postdoctoral research at Columbia University, which followed his PhD studies at the University of British Columbia, in Canada. The earlier portions of Dr. Garcia-Garibay education were completed in his native, Mexico, at the Universidad Michoacana, where he did research on natural product isolation and characterization. Dr. Garcia-Garibay was promoted to full professor in the year 2000 and he has served as Vice Chair for Education in the Department of Chemistry and Biochemistry since 2005. Dr. Garcia-Garibay is a member of the editorial board of the Journal of the American Chemical Society and the Journal of Organic Chemistry. He has been a member of the CNSI since 2005. His current research efforts are aimed to the development of artificial molecular machinery in highly organized crystalline media, and to the development of green chemistry by taking advantage of organic reactions in molecular nanocrystals.

Selected Publications:

Sabrina Simoncelli, Gregory Kuzmanich, Matthew N. Gard, Miguel A. Garcia-Garibay, Photochemical reaction mechanisms and kinetics with molecular nanocrystals: surface quenching of triplet benzophenone nanocrystals, Journal of Physical Organic Chemistry, 2010, 23, 376-381.
Zachary J. O’Brien, Steven D. Karlen, Saeed Khan and Miguel A. Garcia-Garibay, Solid-State Molecular Rotors with Perdeuterated Stators: Mechanistic Insights from Biphenylene Rotational Dynamics in Ordered and Disordered Crystal Forms, J. Org. Chem, 2010, 75 (8), 2482-91.
Rodríguez-Molina B, Pozos A, Cruz R, Romero M, Flores B, Farfán N, Santillan R, Garcia-Garibay MA, Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone, Org Biomol Chem, 2010, 8 (13), 2993-3000.
Lebedeva, N.V.; Tarasov, V.F.; Resendiz, M.J.E.; Garcia-Garibay, M.A.; White, R.C. Forbes, M.D.E. , The Missing Link Between Molecular Triplets and Spin-Polarized Free Radicals: Room Temperature Triplet States of Nanocrystalline Radical Pairs, J. Am. Chem. Soc, 2010, 132, 82-84.
Kuzmanich, G.; Gard, M.N.; Garcia-Garibay, M.A., Photonic Amplification by a Singlet-State Quantum Chain Photodecarbonylation Reaction in Crystalline Diarylcyclopropenones, J. Am. Chem. Soc, 2009, 131, 11606-11614.
Resendiz, M. J. Family, F. Fuller, K. Campos, L. M. Khan, S. I. Lebedeva, N. V. Forbes, M. D. Garcia-Garibay, M. A., Radical reactions with double memory of chirality (2MOC) for the enantiospecific synthesis of adjacent stereogenic quaternary centers in solution: cleavage and bonding faster than radical rotation, J Am Chem Soc, 2009, 131 (24), 8425-33.
Shiraki, S.; Garcia-Garibay, M.A. , Carbon-Carbon Bond Formation By Photoelimination of Small Molecules in Solution and in Crystals, Handbook of Synthetic Photochemistry, 2009, Albini, A., Ed., John Wiley, New York.
Schlundt S, Kuzmanich G, Spänig F, de Miguel Rojas G, Kovacs C, Garcia-Garibay MA, Guldi DM, Hirsch A., Dendritic porphyrin-fullerene conjugates: efficient light-harvesting and charge-transfer events, Chemistry, 2009, 15 (45), 12223-33.
Godinez, C.E.; Garcia-Garibay, M.A., Engineering Crystal Packing and Internal Dynamics in Molecular Gyroscopes by Refining Their Components. Fast Exchange of a Phenylene Rotator by 2H NMR, Cryst. Growth & Design, 2009, 9, 3124-3128.
Ammee Amboya, Tina Nguyen, Hien T. Huynh, Ashley Brown, Gretchen Ratliff, Heather Yonutas, Deniz Cizmeciyan, Arunkumar Natarajan and Miguel A. Garcia Garibay, Radical pairs with rotational fluidity in the photochemical reaction of acetophenone and cyclohexane in the zeolite NAY: a 13C CPMAS NMR and product analysis study, Org. Biomol. Chem, 2009, 7, 2322 - 2326.
Braulio Rodriguez-Molina, Ma. Eugenia Ochoa, Norberto Farfan, Rosa Santillan and Miguel A. Garcia-Garibay, Synthesis, Characterization, and Rotational Dynamics of Crystalline Molecular Compasses with N-Heterocyclic Rotators, J. Org. Chem, 2009, 74 (22), 8554–8565.
Mitsumori, T., Campos, L.M., Garcia-Garibay, M.A., Wudl, F., Sato, H., Sato, Y., Synthesis, Properties, and LED Performance of Highly Luminescent Metal Complexes Containing Indolizino [3,4,5- ab] isoindoles, J. Mat. Chem. , 2009, 19, 5826-5836.
Hoijemberg, P.A.; Karlen, S.D.; Sanramé, C.N.; Aramendia, P.F.; Garcia-Garibay, M.A., Photolysis of an Asymmetrically Substituted Diazene in Solution and in the Crystalline State, Photochem. Photobiol. Sc, 2009, 8, 961-969.
Garcia-Garibay, M. A. Dang, H., Photochemical generation, intramolecular reactions, and spectroscopic detection of oxonium ylide and carbene intermediates in a crystalline ortho-(1,3-dioxolan-2-yl)-diaryldiazomethane, Org Biomol Chem, 2009, 7 (6), 1106-14.
Family, F. Garcia-Garibay, M. A., Photodecarbonylation of ketodiacids as ammonium salts: efficient formation of C-C bonds between adjacent quaternary centers in the crystalline state, J Org Chem, 2009, 74 (6), 2476-80.
Miguel A. Garcia-Garibay, Molecular Machines: Nanoscale gadgets, Nature Materials, 2008, 7, 431-2.
Chin, K. K. Chuang, S. C. Hernandez, B. Campos, L. M. Selke, M. Foote, C. S. Garcia-Garibay, M. A., Photophysical properties of non-homoconjugated 1,2-dihydro, 1,2,3,4-tetrahydro and 1,2,3,4,5,6-hexahydro-C60 derivatives, Photochem Photobiol Sci, 2008, 7 (1), 49-55.
Santillan, R.; Karlen, S.D.; Dang, H.; Garcia-Garibay, M. A., , Synthesis and Characterization of Natural Abundance and Isotopically Labeled 1,4-Bis(3,3,3-triphenylpropynyl)-2,3-difluorobenzene. A Molecular Gyroscope with a Polar Rotator, J. Mex. Chem. Soc., , 2008.
Gould S. L.; Rodriguez, R. B.; Garcia-Garibay, M A. , Synthesis and Solid State Dynamics of Molecular Dirotors, Tetrahedron, 2008, 64, 8336-8345.
Chin, K. K. Trevithick-Sutton, C. C. McCallum, J. Jockusch, S. Turro, N. J. Scaiano, J. C. Foote, C. S. Garcia-Garibay, M. A., Quantitative determination of singlet oxygen generated by excited state aromatic amino acids, proteins, and immunoglobulins, J Am Chem Soc, 2008, 130 (22), 6912-3.
Gould, S. L. Tranchemontagne, D. Yaghi, O. M. Garcia-Garibay, M. A., Amphidynamic character of crystalline MOF-5: rotational dynamics of terephthalate phenylenes in a free-volume, sterically unhindered environment, J Am Chem Soc, 2008, 130 (11), 3246-7.
Kuzmanich, G. Natarajan, A. Chin, K. K. Veerman, M. Mortko, C. J. Garcia-Garibay, M. A., Solid-state photodecarbonylation of diphenylcyclopropenone: a quantum chain process made possible by ultrafast energy transfer, J Am Chem Soc, 2008, 130 (4), 1140-1.
Resendiz, M. J. Taing, J. Khan, S. I. Garcia-Garibay, M. A., Unexpected solid-state photochemistry of an alpha-thiophenyl-alpha'-thiophenyl-S,S-dioxo-substituted ketone, J Org Chem, 2008, 73 (2), 638-43.
Resendiz, M. J. Natarajan, A. Garcia-Garibay, M. A., Diastereoselective synthesis and spin-dependent photodecarbonylation of di(3-phenyl-2-pyrrolidinon-3-yl)ketones: synthesis of nonadjacent and adjacent stereogenic quaternary centers, Chem Commun (Camb), 2008 (2), 193-5.
Chin, K. K. Natarajan, A. Gard, M. N. Campos, L. M. Shepherd, H. Johansson, E. Garcia-Garibay, M. A., Pump-probe spectroscopy and circular dichroism of nanocrystalline benzophenone--towards absolute kinetic measurements in solid state photochemical reactions, Chem Commun (Camb), 2007 (41), 4266-8.
Resendiz, M. J. Taing, J. Garcia-Garibay, M. A., Photodecarbonylation of 1,3-dithiophenyl propanone: using nanocrystals to overcome the filtering effect of highly absorbing trace impurities, Org Lett, 2007, 9 (21), 4351-4.
Nunez, J. E. Natarajan, A. Khan, S. I. Garcia-Garibay, M. A., Synthesis of a triply-bridged molecular gyroscope by a directed meridional cyclization strategy, Org Lett, 2007, 9 (18), 3559-61.
Natarajan, A. Tsai, C. K. Khan, S. I. McCarren, P. Houk, K. N. Garcia-Garibay, M. A., The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed, J Am Chem Soc, 2007, 129 (32), 9846-7.
Natarajan, A.; Ng, D.; Yang, Z.; Garcia-Garibay, M.A., A Green Chemistry Method for the Synthesis of Compounds with Adjacent Quaternary Stereogenic Centers: Parallel Syntheses of (+)- and (-)-alpha-Cuparenone by Radical Combination in Crystalline Solids, Angew Chem. Int. Ed, 2007, 46, 6485-6487.
Grassian, V.H.; Meyer G.; Abruna, H.; Coates, G.W.: Achenie, L.E.; Allison, T.; Brunschwig, B.; Ferry, J.; Garcia-Garibay, M.; Gardea-Torresdey, J.; Grey, C.P.; Hutchison, J.; Li, C.J.; Liotta, C.; Ragauskas, A.; Minteer, S.; Mueller, K.; Roberts, J.; Sadik, O.; Schmehl R.; Schneider, W.; Selloni, A.; Stair, P.; Stewart, J.; Thorn, D; Tyson, J.; Voelker, B.; White, J.M.; Wood-Black, F., Chemistry for a Sustainable Environment, Environmental Science and Technology, 2007, 41, 4840-4846.
Garcia-Garibay, M. A., Molecular crystals on the move: from single-crystal-to-single-crystal photoreactions to molecular machinery, Angew Chem Int Ed Engl, 2007, 46 (47), 8945-7.
Chin, K.K.; Natarajan, A.; Gard, M.; Campos, L. M.; Johansen, E.; Shepherd, H.; Garcia-Garibay, M. A., Organic Molecular Nanocrystals: Triplet -Triplet Absorption, Phosphorescence, and Circular Dichroism of Chiral Crystals of Benzophenone, Chem. Comm, 2007, 4266-4268.
Natarajan, A. Ng, D. Yang, Z. Garcia-Garibay, M. A., Parallel syntheses of (+)- and (-)-alpha-cuparenone by radical combination in crystalline solids, Angew Chem Int Ed Engl, 2007, 46 (34), 6485-7.
Campos, L. M.; Garcia-Garibay, M. A., Reactive Intermediates in Crystals: Form and Function, Reviews of Reactive Intermediate Chemistry, Platz, M. S.; Jones, M.; Moss, R. Eds, 2007.
Jarowski, P. D. Houk, K. N. Garcia-Garibay, M. A., Importance of correlated motions on the low barrier rotational potentials of crystalline molecular gyroscopes, J Am Chem Soc, 2007, 129 (11), 3110-7.
Khuong, T. A. Dang, H. Jarowski, P. D. Maverick, E. F. Garcia-Garibay, M. A., Rotational dynamics in a crystalline molecular gyroscope by variable-temperature 13C NMR, 2H NMR, X-ray diffraction, and force field calculations, J Am Chem Soc, 2007, 129 (4), 839-45.
Chin, K. K. Chuang, S. C. Hernandez, B. Selke, M. Foote, C. S. Garcia-Garibay, M. A., Photophysical properties of a 1,2,3,4,5,6-hexasubstituted fullerene derivative, J Phys Chem A, 2006, 110 (51), 13662-6.
Karlen, Steven D.; Garcia-Garibay, Miguel A. , Amphidynamic Crystals: Structureal Blueprints for Molecular Machines, Topics Curr. Chem, 2006, 262, 179-228.
Choe, T.; Saeed I. Khan, S.I.; Garcia-Garibay, M.A., Combination Vs Disproportionation in Dialkyl Biradicals. Selectivity Reversal in a Crystalline Solid, Photochem.& Photobiol. Sc, 2006, 5, 449-451.
Nunez, J. E.; Khuong, T.-A.V.; Farfan, N.; Dang, H.; Garcia-Garibay, M.A. , Crystal Phases and Phase Transitions in a Highly Polymorphogenic Molecular Gyroscope with meta-Methoxytrityl Frames , Cryst. Growth & Design, 2006, 5, 866-873.
Khuong, T.-A. V.; Nunez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A., Crystalline Molecular Machines: A Quest Towards Solid State Dynamics and Function, Acc. Chem. Res, 2006, 39, 413-422.
Mortko, Christipher J.; Garcia-Garibay, Miguel A., Engineering Stereospecific Reactions in Crystals: Synthesis of Compounds with Adjacent Stereogenic Quaternary Centers by Photodecarbonylation of Crystalline Ketones, Top. Stereochem, 2006, 25, 205-253.
Karlen, S.D.; Godinez, C. E.; Garcia-Garibay, M.A., Improved Physical Properties and Rotational Dynamics in a Molecular Gyroscope with an Asymmetric Stator Structure, Organic Letters, 2006, 8, 3417 - 3420.
Radhakrishnan, C.; Lo, M.K.F.; Warrier, M.V.; Garcia-Garibay, M.A., Photocatalytic Reduction of Azide Self-Assembled Monolayer using CdS Quantum Dots, Langmuir , 2006, 22, 5018-5024.
Veerman, M. Resendiz, M. J. Garcia-Garibay, M. A., Large-scale photochemical reactions of nanocrystalline suspensions: a promising green chemistry method, Org Lett, 2006, 8 (12), 2615-7.
Garcia-Garibay, M. A. , Crystalline molecular machines: encoding supramolecular dynamics into molecular structure, Proc Natl Acad Sci U S A, 2005, 102, 10771-10776.
Campos, LM Warrier, MV Peterfy, K Houk, KN Garcia-Garibay, MA, Secondary alpha isotope effects on deuterium tunneling in triplet o-methylanthrones: extraordinary sensitivity to barrier width, J Am Chem Soc , 2005, 127, 10178-9.
Horansky, R. D.; Clarke, L. I.; Price, J. C.; Khuong, T.-A.V.; Jarowski, P D.; Garcia-Garibay, M.A., "Dielectric Response of a Dipolar Molecular Rotor Crystal", Phys. Rev. B, 2005, 72, 014302.
Cizmeciyan, D. Yonutas, H. Karlen, S. D. Garcia-Garibay, M. A. , H-2 NMR and X-ray diffraction studies of methyl rotation in crystals of ortho-methyldibenzocycloalkanones, Solid State Nucl Magn Reson, 2005, 28, 1-8.
Mortko, C. J. Garcia-Garibay, M. A., Green chemistry strategies using crystal-to-crystal photoreactions: stereoselective synthesis and decarbonylation of trans-alpha,alpha'-dialkenoylcyclohexanones, J Am Chem Soc, 2005, 127 (22), 7994-5.
Karlen, S. D. Ortiz, R. Chapman, O. L. Garcia-Garibay, M. A. , Effects of rotational symmetry order on the solid state dynamics of phenylene and diamantane rotators, J Am Chem Soc, 2005, 127, 6554-5.
Resendiz, M. J. Garcia-Garibay, M. A., Hammett analysis of photodecarbonylation in crystalline 1,3-diarylacetones, Org Lett, 2005, 7 (3), 371-4.
Karlen, S. D. Garcia-Garibay, M. A., Highlighting gyroscopic motion in crystals in 13C CPMAS spectra by specific isotopic substitution and restricted cross polarization, Chem Commun (Camb), 2005, volume (2), 189-91.
Khuong, T. A. Zepeda, G. Sanrame, C. N. Dang, H. Bartberger, M. D. Houk, K. N. Garcia-Garibay, M. A., Crankshaft motion in a highly congested bis(triarylmethyl)peroxide, J Am Chem Soc, 2004, 126 (45), 14778-86.
Warrier, M. Lo, M. K. Monbouquette, H. Garcia-Garibay, M. A., Photocatalytic reduction of aromatic azides to amines using CdS and CdSe nanoparticles, Photochem Photobiol Sci, 2004, 3 (9), 859-63.
Godinez, C. E. Zepeda, G. Mortko, C. J. Dang, H. Garcia-Garibay, M. A., Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames, J Org Chem, 2004, 69 (5), 1652-62.
Ng, D. Yang, Z. Garcia-Garibay, M. A., Total synthesis of (+/-)-herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone, Org Lett, 2004, 6 (4), 645-7.
Dominguez, Z. Khuong, T. A. Dang, H. Sanrame, C. N. Nunez, J. E. Garcia-Garibay, M. A., Molecular compasses and gyroscopes with polar rotors: synthesis and characterization of crystalline forms, J Am Chem Soc, 2003, 125 (29), 8827-37.
Ellison, M. E. Ng, D. Dang, H. Garcia-Garibay, M. A., Enantiospecific synthesis of vicinal stereogenic tertiary and quaternary centers by combination of configurationally-trapped radical pairs in crystalline solids, Org Lett, 2003, 5 (14), 2531-4.
Garcia-Garibay, M. A., Engineering carbene rearrangements in crystals: from molecular information to solid-state reactivity, Acc Chem Res, 2003, 36 (7), 491-8.
Amirsakis, D. G. Elizarov, A. M. Garcia-Garibay, M. A. Glink, P. T. Stoddart, J. F. White, A. J. Williams, D. J., Diastereospecific photochemical dimerization of a stilbene-containing daisy chain monomer in solution as well as in the solid state, Angew Chem Int Ed Engl, 2003, 42 (10), 1126-32.
Dominguez, Z. Dang, H. Strouse, M. J. Garcia-Garibay, M. A., Molecular "compasses" and "gyroscopes." III. Dynamics of a phenylene rotor and clathrated benzene in a slipping-gear crystal lattice, J Am Chem Soc, 2002, 124 (26), 7719-27.
Godinez, C. E. Zepeda, G. Garcia-Garibay, M. A., Molecular compasses and gyroscopes. II. Synthesis and characterization of molecular rotors with axially substituted bis[2-(9-triptycyl)ethynyl]arenes, J Am Chem Soc, 2002, 124 (17), 4701-7.
Dominguez, Z. Dang, H. Strouse, M. J. Garcia-Garibay, M. A., Molecular "compasses" and "gyroscopes". I. Expedient synthesis and solid state dynamics of an open rotor with a bis(triarylmethyl) frame, J Am Chem Soc, 2002, 124 (11), 2398-9.
Dang, H. Levitus, M. Garcia-Garibay, M. A., One step Pd(0)-catalyzed synthesis, X-ray analysis, and photophysical properties of cyclopent[hi]aceanthrylene: fullerene-like properties in a nonalternant cyclopentafused aromatic hydrocarbon, J Am Chem Soc, 2002, 124 (1), 136-43.
Yang, Z. Ng, D. Garcia-Garibay, M. A., Engineering reactions in crystalline solids: photochemical generation of secondary and tertiary enol radical pairs from crystalline ketodiesters, J Org Chem, 2001, 66 (13), 4468-75.
Levitus, M. Schmieder, K. Ricks, H. Shimizu, K. D. Bunz, U. H. Garcia-Garibay, M. A., Steps to demarcate the effects of chromophore aggregation and planarization in poly(phenyleneethynylene)s. 1. Rotationally interrupted conjugation in the excited states of 1,4-bis(phenylethynyl)benzene, J Am Chem Soc, 2001, 123 (18), 4259-65.
Levitus, M. Zepeda, G. Dang, H. Godinez, C. Khuong, T. A. Schmieder, K. Garcia-Garibay, M. A., Steps to demarcate the effects of chromophore aggregation and planarization in poly(phenyleneethynylene)s. 2. The photophysics of 1,4-diethynyl-2-fluorobenzene in solution and in crystals, J Org Chem, 2001, 66 (9), 3188-95.
Dang, H. Garcia-Garibay, M. A., Palladium-catalyzed formation of aceanthrylenes: a simple method for peri-cyclopentenelation of aromatic compounds, J Am Chem Soc, 2001, 123 (2), 355-6.
Yang, Z. Garcia-Garibay, M. A., Engineering Reactions in Crystalline Solids: Radical Pairs in Crystals of Dialkyl 1,3-Acetonedicarboxylates, Org Lett, 2000, 2 (13), 1963-1965.