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Organic Photochemistry Group

The Organic Photochemistry Group (GRUFOR) was first established at the University of La Rioja in 1993, and is currently constituted by researchers and teaching staff who are in charge of different research lines. The main topic of these studies is the photochemical behavior of different organic and organometallic systems, considering it from a synthetic, mechanistic and theoretical point of view. During the last few years, our research has also covered the study of molecular devices whose movements are induced by light, and the application of theoretical calculations to chemical reactivity.

Research lines

Design, synthesis and photochemical characterization of biomimetic molecular switches and (+)

Design, synthesis and photochemical characterization of biomimetic molecular switches and motors

The use of computational chemistry has allowed the design of molecules whose movements are induced by light absorption which mimic natural systems. The design patterns have been used for the synthesis of molecules that behave as molecular switches and motors. These systems are based on the PSB retinal chromophore and the green fluorescent protein (GFP) chromophore. When chirality is introduced in the structure, these compounds perform a unidirectional movement. Once synthesized, it is possible to study their spectroscopic and photochemical properties. The next step envisaged is the introduction of these molecular devices in more complex chemical or biological systems.

Photochemical synthetic methodology. Photolysis of iodinated derivatives (+)

Photochemical synthetic methodology. Photolysis of iodinated derivatives

Another new research line has been started based on the acquired experience during the N-O bonds photolysis processes and the generation of radicals. It consists of the synthesis of polycyclic systems through the photolysis of C-I bonds. Thus, the resulting carbon-free radicals can react in an intra or intermolecular way with several p-systems to achieve aromatic carbocycles and related compounds.

Computational photochemistry (+)

Computational photochemistry

Diverse photochemical reactions that have great interest are studied using the most powerful computational tools available nowadays for this kind of reactivity. Specifically, the reactivity of certain organic chromophores is analyzed with CASSCF/CASPT2 strategy at the singlet or triplet state. Really appealing results were obtained when studying the photochemical N-ciclopropylimine-1-pyrroline transposition, and the [2+2] cycloaddition and electrocyclization of 1-azadienes. This computational methodology has also allowed the design of new molecules with photoactive properties.

Photoprotective compounds (+)

Photoprotective compounds

Starting from the computational study of natural compounds with excellent photoprotective properties in diverse species, we are trying to figure out the highly efficient mechanism that these organisms use in order to protect themselves against UV light. Moreover, we attempt to design a new family of compounds that allows either improving the properties of the natural compounds, or providing it with interesting properties and behavior. Once synthesized, the next step is the practical application of these compounds. Due to the increase of interest provided by these kinds of compounds in the last few years for their use in sunscreens and plastic and paint additives, it is reasonable to demonstrate their photoprotective capability.

Polymers, photochemistry and environment (+)

Polymers, photochemistry and environment

In collaboration with several companies polymers have been designed and prepared with special properties. Recent examples include water soluble polyester resins for use in water paints and varnishes, permeable gas rubbers or polyurethane-based composites with good acoustic and insulating properties. It has also been applied in the curing of resins, both in the study of the processes as in the preparation of new components for use in the coatings industry.

Photochemistry of nitrogenated systems; theoretical and experimental studies (+)

Photochemistry of nitrogenated systems; theoretical and experimental studies

The photochemistry of nitrogenated compounds has been the main research line in this group since it was established 20 years ago. The electrocyclization of 1- and 2- azadienes, the photoreactivity of iminocarbenes, the novel photochemical N-ciclopropylimine-1-pyrroline transposition, the [2+2] cycloaddition between imines and alkenes, and the photolysis of oxime derivatives, are just a few examples of the kind of studies that have been done. The last mentioned topic has led to a new research branch that consists of the use of the iminyl radicals generated by the photolysis of oxime derivatives in order to synthesize nitrogenated heterocycles and natural products. Moreover, it is possible the preparation of systems including extended conjugations over heteroaromatic policycles may be used as sensors.

Group research

Latest publications

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Rational Design and Synthesis of Efficient Sunscreens To Boost the Solar Protection Factor

Raúl Losantos, Ignacio Funes-Ardoiz, José Aguilera, Enrique Herrera-Ceballos,Cristina García-Iriepa, Pedro J. Campos, and Diego Sampedro
Angew. Chem. Int. Ed., 2017, 56, 10, 2632 –2635

A biomimetic molecular switch at work: coupling photoisomerization dynamics to peptide structural rearrangement

Cristina García-Iriepa, Moussa Gueye, Jérémie Léonard, David Martínez-López, Pedro J. Campos, Luis Manuel Frutos, Diego Sampedro and Marco Marazzi
Physical Chemistry Chemical Physics, 2016

Hydantoin-Based Molecular Photoswitches

David Martínez-López, Meng-Long Yu, Cristina García-Iriepa, Pedro J. Campos, Luis Manuel Frutos, James A. Golen, Sivappa Rasapalli, Diego Sampedro
J. Org. Chem., 2015, 80, 3929−3939

Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring

Sara Gutiérrez, David Martí†nez-López, Mar†a Morón, David Sucunza, Diego Sampedro, Alberto Domingo, Antonio Salgado, and Juan J. Vaquero
Chemistry. A European Journal, 2015, 21, 18758 – 18763

Steric Enhancement of the Chemiluminescence of Luminols

Axel G. Griesbeck, Yrene D†az-Miara, Robert Fichtler, Axel Jacobi von Wangelin, Raúl Pérez-Ruiz, and Diego Sampedro
Chemistry. A European Journal, 2015, 21, 9975 – 9979

I + D Projects

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Sistemas fotoactivos: aplicaciones biológicas y de almacenamiento de energía

Ministerio de Economía y Competitividad (CTQ2014-59650-P)
01/01/2015 to 31/12/2017

Latest congress communications

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Latest invited conferences

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PhD thesis works

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Estudio del comportamiento fotoquímico y electroquímico de yodoalquenos

Author: Héctor F. González Cruz
Director: Pedro J. Campos y Miguel A. Rodríguez
Date: 27/09/2013
Universidad de La Rioja

Synthesis and applications of new biomimetic molecular switches

Author: Marina Blanco Lomas
Director: Diego Sampedro Ruiz, Pedro J. Campos García
Date: 26/07/2012
Universidad de La Rioja

Aplicaciones derivadas de la fotoquímica de O-aciloximas

Author: Alegría Caballero Millán
Director: Miguel A. Rodríguez Barranco, Pedro J. Campos García
Date: 26/09/2012
Universidad de La Rioja

Diseño, síntesis y caracterización de interruptores moleculares biomiméticos

Author: Laura Rivado Casas
Director: Pedro J. Campos García, Diego Sampedro Ruiz
Date: 12/02/2010
Universidad de La Rioja

Irradiación de aciloximas y su participación en procesos de ciclación intramolecular

Author: Rafael Alonso Ruiz
Director: Miguel A. Rodríguez, Pedro J. Campos
Date: 14/03/2008
Universidad de La Rioja

Master thesis works

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Modulación de propiedades antibióticas por luz

Author: Elena Contreras García
Director: Diego Sampedro Ruiz
Course: 2014/15
Universidad de La Rioja

Síntesis y estudio fotoquímico de análogos de aminoácidos tipo micosporina

Author: Raúl Losantos Cabello
Director: Diego Sampedro Ruiz
Course: 2013/14
Universidad de La Rioja

Estudio fotoquímico de compuestos fotoisomerizables

Author: David Martínez López
Director: Diego Sampedro y Marina Blanco
Course: 2012/13
Universidad de La Rioja

Participation in other master programs

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Máster en Química Avanzada

Subject: Química Computacional
Lecturer: Miguel A. Rodríguez Barranco
From 2007/08 course
Universidad de Burgos
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Máster en Química Sintética e Industrial

Subject: Fotoquímica Orgánica
Lecturer: Diego Sampedro Ruiz; Pedro J. Campos García
From 2007/08 course
Universidad del País Vasco y Pública de Navarra
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National and international relations

Ballesteros Gimeno, Alfredo. Inst. Química Organometálica "Enrique Moles", Universidad de Oviedo
Jiménez Molero, Consuelo. Instituto de Tecnología Química, Universidad Politécnica de Valencia. España
Wooley, G. Andrew. Department of Chemistry, University of Torinto. Canadá
García Gómez, Hermenegildo. Instituto de Tecnología Química, Universidad Politécnica de Valencia. España
Barluenga Mur, José J.. Instituto Universitario de Química Organometálica "Enrique Moles". Universidad Politécnica de Val. España
González Díaz, José Manuel. Instituto de Química Organometálica, "Enrique Moles", Universidad de Oviedo
Frutos Gaite, Luís Manuel. Departamento de Química-Física, Universidad de Alcalá, Madrid. España
Olivucci, Massimo. Dipartimento di Chimica, Università di Siena. Siena. Italia
Miranda Alonso, Miguel A.. Instituto de Tecnología Química, Universidad Politécnica de Valencia
Castaño González, Obis. Dpto. Química-Física, Universidad Alcalá. España
Braslavsky, Silvia. Max-Planck-Institut für Strahlenchemie, Mülheim-Ruhr. Alemania
Scaiano, Tito. Department of Chemistry, University of Ottawa. Canadá