Carbon Nanostructures and Perylenediimides

The seeking for efficient molecular systems, based on the covalent combination of suitable and versatile building blocks, capable to mimic the photoinduced electron transfer that naturally occurs in photosynthesis, has been a constant in material science.[1] In a simplistic definition, a molecular system which combines an electron-acceptor moiety with an electron-donor counterpart, able to be excited by the action of light, can be considered as a potential photosynthetic system, and therefore useful for photovoltaic applications.

Among the large number of donor-acceptor molecules frequently used in the preparation of photo-electroactive molecular systems, carbon nanostructures (CNs) and perylenediimides (PDIs) stand out. So far, we can find examples where the CNs are covalently or supramolecularly attached to PDI subunits, thus combining the electrochemical and photophysical properties of the former with the electrochemical and light-absorption properties of the latter.[2] In most of the cases, both sytems are electron deficient and energy transfer between them is observed. However, to the best of our knowledge, the synthesis of CN-PDI where the PDI acts an electron donor has only been briefly described. This kind of systems is quite interesting because it will be possible to study the influence of the electronic interaction between both units in different configurations.

Herein, we will report our more recent results related with the synthesis of different carbon nanostructure-perylenediimide arrays where the PDI acts as an electron-donor system (see Figure 1 as example), focussing mainly in the photoinduced electron transfer properties for their application as artificial photosynthetic systems and in organic photovoltaics.[3]

                       

Acknowledgements. This work has been supported by the Spanish Ministerio de Economía y Competitividad, Generalitat Valenciana and the European FEDER funds (grants CTQ2011-26455, PROMETEO 2012/010 and ISIC/2012/008)

  References

1.  (a) El-Khouly, M. E.; Fukuzumi, S.; D’Souza, F. ChemPhysChem, 2014, 15, 30.

 2. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268.

3. (a) Martín-Gomis, L.; Giorgo, R.; Ohkubo, K.; Fernández-Lázaro, F.; Tagmatarchis, N.; Fukuzumi S.; Sastre-Santos Á. Submitted. (b) Martín-Gomis, L.; Karousis, N.; Petsalakis, I. D.; Ohkubo, K.; Fernández-Lázaro, F.; Tagmatarchis, N.; Fukuzumi S.; Sastre-Santos Á. Submitted.

Figure 1. Chemical structure of [60]Fullerene-PDI system