Pablo Rivera Fuentes

 

PhD Student

Location:

HCI G-306

Phone:

+41-44-632 2912

e-mail:

Pablo Rivera Fuentes

Education

2003-2007:

Bachelor study of Chemical Engineering at Universidad Nacional Autonoma de Mexico.

2007:

BSc Thesis with Prof. Dr. G. Cuevas at Universidad Nacional Autonoma de Mexico.

2008-2009:

Master study of Chemistry at ETH Zurich.

2009:

MSc Thesis with Prof. Dr. F. Diederich at ETH Zurich.

2009-2012:

PhD student with Prof. Dr. F. Diederich at ETH Zurich.

3D Acetylenic Scaffolding Using Enantiomerically Pure 1,3-Diethynylallenes (DEAs)


Recently, we have described the preparation of enantiomerically pure DEAs by asymmetric synthesis and HPLC separation on a chiral stationary phase. These building blocks have been so far used to induce chirality in tetracyanobutadiynes (TCBDs) and to synthesize the first enantiomerically pure alleno-acetylenic macrocycle. The absolute configuration of the DEAs, the mechanism of chiral induction into TCBDs, and the outstanding chiroptical response of the alleno-acetylenic macrocycle have been studied using circular dichroism spectroscopy and quantum mechanical calculations. Current studies using enantiopure DEAs include the construction of conformationally-stable foldamers, investigation of the effect of allene chirality in the electronic properties of macrocycles, and the design of lateral chains to stabilize supramolecular structures with the potential to reach unprecedented values of circular dichroism.

Publications

J. L. Alonso-Gómez, P. Schanen, P. Rivera-Fuentes, P. Seiler, F. Diederich, Chem. Eur. J. 2008, 14, 10564-10568. 1,3-Diethynylallenes (DEAs): Enantioselective Synthesis, Absolute Configuration, and Chiral Induction in 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs).

A. Kraszewska, P. Rivera-Fuentes, C. Thilgen, F. Diederich, New J. Chem. 2009, 33, 386-396. First Enantiomerically Pure C-70-adducts with a Non-inherently Chiral Addition Pattern.

J. L. Alonso-Gómez, A. G. Petrovic, N. Harada, P. Rivera-Fuentes, N. Berova, F. Diederich, Chem. Eur. J. 2009, 15, 8396-8400. Chiral Induction from Allenes into Twisted 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs): Conformational Assignment by Circular Dichroism Spectroscopy.

J. L. Alonso-Gómez, P. Rivera-Fuentes, N. Harada, N. Berova, F. Diederich, Angew. Chem. Int. Ed. 2009, 38, 5545-5548. An Enantiomerically Pure Alleno-acetylenic Macrocycle: Synthesis and Rationalization of its Outstanding Chiroptical Response. Very Important Paper, Cover Picture.

P. Rivera-Fuentes, J. L. Alonso-Gómez, A. G. Petrovic, F. Santoro, N. Harada, N. Berova, F. Diederich, Angew. Chem. Int. Ed. 2010, 49, 2247-2250. Amplification of Chirality in Monodisperse, Enantiopure Alleno-Acetylenic Oligomers.

M. Yamada, P. Rivera-Fuentes, W. B. Schweizer, F. Diederich, Angew. Chem. Int. Ed. 2010, 49, 3532-3535. Optical Stability of Axially Chiral Push-Pull-Substituted Buta-1,3-dienes: Effect of a Single Methyl Group on the C60 Surface.

B. Buschhaus, V. Convertino, P. Rivera-Fuentes, J. L. Alonso-Gómez, A. G. Petrovic, F. Diederich, Eur. J. Org. Chem. 2010, 2452-2456. Optically Active Trialkynyl(phenyl)methane: Synthesis and Determination of its Absolute Configuration by Vibrational Circular Dichroism (VCD) and Optical Rotatory Dispersion (ORD).

A. Kraszewska, P. Rivera-Fuentes, G. Rapenne, J. Crassous, A. G. Petrovic, J. L. Alonso-Gómez, E. Huerta, F. Diederich, C. Thilgen, Eur. J. Org. Chem. 2010, 4402-4411. Regioselectivity in Tether Directed Remote Functionalization - Reinvestigation of the Addition of a CTV Based Tris-Tether to C60.

P. Rivera-Fuentes, J. L. Alonso-Gómez, A. G. Petrovic, F. Santoro, P. Seiler, N. Harada, N. Berova, H. S. Rzepa, F. Diederich, Chem. Eur. J. 2010, 16, 9796-9807. Enantiomerically Pure Alleno-Acetylenic Macrocycles: Synthesis, Solid State Structures, Chiroptical Properties, and Electron Localization Function Analysis. Inside Cover Picture.

P. Rivera-Fuentes, B. Nieto-Ortega, W. B. Schweizer, J. T. López Navarrete, J. Casado, F. Diederich, Chem. Eur. J. 2011, 17, 3876-3885. Enantiopure, Monodisperse Alleno-acetylenic Cyclooligomers: Effect of Symmetry and Conformational Flexibility on the Chiroptical Properties of Carbon-rich Compounds. Very Important Paper.

F. Silvestri, M. Jordan, K. Howes, M. Kivala, P. Rivera-Fuentes, C. Boudon, J.-P. Gisselbrecht, W. B. Schweizer, P. Seiler, M. Chiu, F. Diederich, Chem. Eur. J. 2011, 17, 6088-6097. Regular Acyclic and Macrocyclic [AB] Oligomers by Formation of Push-Pull Chromophores in the Chain-Growth Step.

C. M. Reisinger, P. Rivera-Fuentes, S. Lampart, W. B. Schweizer, F. Diederich, Chem. Eur. J. 2011, 17, 12906-12911. Cascade Pericyclic Reactions of Alleno-Acetylenes: Facile Access to Highly Substituted Cyclobutene, Dendralene, Pentalene, and Indene Skeletons.

P. Rivera-Fuentes, F. Diederich, Angew. Chem. Int. Ed. 2012, 51, 2818-2828. Allenes in Molecular Materials.

V. Ehmke, J. E. Q. Quinsaat, P. Rivera-Fuentes, C. Heindl, C. Freymond, M. Rottmann, R. Brun, T. Schirmeister, F. Diederich, Org. Biomol. Chem. 2012, DOI: 10.1039/c2ob00034b. Tuning and Predicting Biological Affinity: Aryl Nitriles as Cysteine Protease Inhibitors.

P. Rivera-Fuentes, M. von Wantoch Rekowski, W. B. Schweizer, J.-P. Gisselbrecht, C. Boudon, F. Diederich, in preparation.

Last update: Apr. 2012