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Miguel Garcia-Garibay, Ph.D.

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

Education:
Degrees:
Ph.D., University of British Columbia, 1988

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

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

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

Contact Information:
Email Address: mgg@chem.ucla.edu
Laboratory Address: Mol Sci Bldg 4235
Work Address: Mol Sci Bldg 4505C
Home Page: http://www.chem.ucla.edu/dept/Faculty/mgghome/
ARR Papers: http://www.cnsi.ucla.edu/arr/personnel-papers?personnel_id=117155
Lab Number: 1 (310) 206-1275 Lab
Work Phone Number: 1 (310) 825-3159 Office
Research Interests:

Solid-state organic chemistry and molecular nanocrystals, photochemistry and spectroscopy, solid-state reaction mechanisms, dipolar lattices and molecular machines.


Technical Research Interest:

The Garcia-Garibay research group is dedicated to the study of solids and crystalline materials spanning a wide range of properties and length scales. There are four main research thrusts in the group (I) The design of reactions in crystals for both synthetic and materials applications; (II) The design of solid state materials with functions that rely on controlled mechanical changes at the molecular level, including electrooptics, ferroelectrics, etc. (III) The use of nanoparticles to control photochemical processes, and (IV) the study of structure- reactivity correlations based on solid state reaction rates and X-Ray structural analyses, including the control of reactive intermediates and a better understanding of quantum mechanical tunneling.


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:

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.
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.
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.
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. 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.
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.
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, 6912-6913.
Kuzmanich, G.; Natarajan, A,; Chin, K. K.; Veerman, M.; Mortko, C. J.; Garcia-Garibay, M. A., Solid State Photodecarbonylation of Diphenylcyclopropenone: A Singlet State Quantum Chain Reaction Made Possible by Ultrafast Energy Transfer, J. Am. Chem. Soc, 2008, 130, 1140-1141.
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.
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.
Resendiz, M. J. E.; Taing, J.; Khan, S. I.; Garcia-Garibay, M. A., Unexpected Solid State Photochemistry of an apha-Thiophenyl-alpha'-Thiophenyl-S,S-dioxo Substituted Ketone, J. Org. Chem, 2008, 73, 638-643.
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.
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.
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.
Garcia-Garibay, Miguel A. , Molecular Crystals on the Move: From Single Crystal-to-Single Crystal Photoreactions to Molecular Machinery, Angew Chem. Int. Ed, 2007, 8945-8947.
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.
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.
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.
Resendiz, Marino J.E.; Taing, Jennifer; Garcia-Garibay, Miguel A., Photodecarbonylation of 1,3-Dithiophenyl Propanone: Using Nanocrystals to Overcome the Filtering Effect of Highly Absorbing Trace Impurities, J. Org. Chem, 2007, 9, 4351-4354.
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.
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.
Khuong, T.-A. V.; Dang, H.; Jarowski, P. D.; Emily F. Maverick and Miguel A. Garcia-Garibay, Rotational Dynamics of a Crystalline Molecular Gyroscope by Variable Temperature 13C NMR, 2H NMR, X-Ray Diffraction and Force Field Calculations, J. Am. Chem. Soc, 2007, 129, 839-845.
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.
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.
Nunez, Jose E.; Natarajan, Arunkumar; Khan, Saeed I.; Garcia-Garibay, Miguel A., Synthesis of a Triply-Bridged Molecular Gyroscope by a Directed Meridional Cyclization Strategy, Organic Lett, 2007, 9, 3559-3561.
Jarowski, P.D.; Houk, K. N.; Garcia-Garibay, M.A., The Importance of Correlated Motions on the Low Barrier Rotational Potentials of Crystalline Molecular Gyroscopes, J. Am. Chem. Soc., 2007, 129, 3110-3117.
Natarajan, A.; Tsai, C. K.; Khan, S. I.; McCarren, P.; Houk, K. N.; Garcia-Garibay, Miguel 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, 9846-9847.
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.
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.
Khuong, T. A. Nunez, J. E. Godinez, C. E. Garcia-Garibay, M. A. , Crystalline molecular machines: a quest toward solid-state dynamics and function, Acc Chem Res, 2006, 39 (6), 413-22.
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.
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, Org Lett, 2006, 8 (16), 3417-20.
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.
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.
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.
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.
Garcia-Garibay, M. A. , Crystalline molecular machines: encoding supramolecular dynamics into molecular structure, Proc Natl Acad Sci U S A, 2005, 102, 10771-10776.
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.
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.
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.
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.
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.
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.
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.
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.
Warrier, M Lo, MK Monbouquette, H Garcia-Garibay, MA, Photocatalytic reduction of aromatic azides to amines using CdS and CdSe nanoparticles, Photochem. & Photobiol. Sc, 2004, 3, 859-63.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.



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