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Séminaire Chimie ED459

Tuning on properties in multicomponent organic solids

Prof. Hugo Morales-Rojas (Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, México)

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Le Jeudi 10 novembre 2016 à 13h45
UM FdS, Salle de Cours SC-16.01

In recent years, supramolecular strategies to assemble multicomponent solids and materials have provided with synthetic methods to endow new properties in the solid state. In this talk two approaches taken in our group will be highlighted that involve the study of : (i) pharmaceutical cocrystals, and (ii) nitrogen-boron adducts that self-assemble to form solids with recognition abilities. A brief introduction to these research topics is given below.

Pharmaceutical cocrystals :
Active pharmaceutical ingredients (APIs) are one of the most valuable chemicals for modern human life. Nevertheless, they suffer of several limitations due to their physical and biopharmaceutical properties. Poorly performing solid-state APIs (with low solubility and low permeability) are dominant in the current pharmaceutical field. To overcome these limitations, combination of APIs with other small molecules forming new and homogeneous cocrystalline solids is being investigated.

Nitrogen-boron assemblies :
Lewis type adducts assembled via nitrogen-boron bonds (N→B) have been used to form several types of supramolecular macrocycles, cages and soft materials. In our group, we have used this strategy to form tunable clathrates assembled in one-step from three or four molecular components that can incorporate a single or a blend of polycyclic aromatic hydrocarbons (PAHs) into crystalline solids at room temperature. The resulting organic clathrates can perform “catch and release” cycles of PAHs, and can sequester selectively PAHs from mixtures in solution.

Recent References

1. J. M. Martínez-Alejo, J. G. Domínguez-Chávez, J. Rivera-Islas, D. Herrera-Ruiz, H. Höpfl, H. Morales-Rojas, and J. P. Senosiain “A Twist in Cocrystals of Salts : Changes in Packing and Chloride Coordination Lead to Opposite Trends in Biopharmaceutical Performance of Fluoroquinolone Hydrochloride Cocrystals”, Cryst. Growth. Des. 2014, 14, 3078–3095. DOI 10.1021/cg500345a
2. O. Sánchez-Guadarrama, F. Mendoza-Navarro, A. Cedillo-Cruz, H. Jung-Cook, J. I. Arenas-García, A. Delgado-Díaz, D. Herrera-Ruiz, H. Morales-Rojas, H. Höpfl, “Chiral resolution of RS-Praziquantel via Diastereomeric Cocrystal Pair Formation with L-Malic Acid”, Cryst. Growth. Des. 2016, 16, 307–314. DOI 10.1021/acs.cgd.5b01254
3. A.D. Herrera-España, G. Campillo-Alvarado, P. Román-Bravo, D. Herrera-Ruiz, H. Höpfl, H. Morales-Rojas, “Selective Isolation of Polycyclic Aromatic Hydrocarbons by Self-Assembly of a Tunable N→B Clathrate”, Cryst. Growth. Des. 2015, 15, 1572. DOI 10.1021/acs.cgd.5b00219

Biosketch :
Hugo Morales-Rojas is Professor of Chemistry at the Centro de Investigaciones Químicas of the Universidad Autónoma del Estado de Morelos in Cuernavaca, México. He graduated from the National University in Mexico (UNAM) working with Prof. Anatoly Yatsimirsky, and as a Fulbright Scholar obtained his PhD in Physical Organic Chemistry in 2001 at Rutgers University (New Jersey, USA) under the guidance of Prof. Robert A. Moss. After a postdoctoral stay at Stanford University with Prof. Eric T. Kool (2002), he moved to Cuernavaca to join the Supramolecular and Inorganic Chemistry research team investigating various supramolecular systems such as metallomacrocycles, pharmaceutical cocrystals and other multicomponent crystalline materials. He is author of more than 30 peer-reviewed publications including 4 granted patents. He is a member of the Mexican Research System (SNI Level 2), and the American Chemical Society.
Prof. Morales-Rojas is currently spending a sabbatical stay at ICGM in the IMNO team with Dr. J.-O. Durand.

Contact local ICGM : Dr. Jean-Olivier Durand, D.R. CNRS (équipe IMNO)

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