Proceedings of 6th International Conference on Hybrid and Organic Photovoltaics (HOPV14)
Publication date: 1st March 2014
Here we present a computational and spectroscopic study on a family of cheap, non-toxic, environmentally friendly flavylium sensitizers.[1] We followed a bio-inspired strategy and with the adequate structural modifications of the 2-phenyl-1-benzopyrylium core (flavylium) prepared quasi-natural biomimetic dyes. With this strategy we prepared a series of new anthocyanin analogues. Among these, in the compound
7-(N,N-diethylamino)-3’,4’-dihydroxyflavylium (AD65),which is our best sensitizer, the diethylamine acts as an electron donor (D), the catechol moiety complexing with Ti(IV) in ring B behaves as an acceptor (A) and the benzopyran systems (rings A and C) constitute a π bridge defining a D–π–A structure similar to a “push and pull” sensitizer. More recently, with AD65 we obtained a solar conversion efficiency of 3.6% with an open circuit voltage of 0.4 V and a short-circuit current density of 16 mA/cm2. We have available in the team a library of flavylium derivatives and expertise to design and synthesize new compounds with potential higher photovoltaic performances.[2] In order to improve the DSSC performances, part of our strategy involves extending the absorption range to the near-IR regime in order to attain good overlap with the solar emission spectrum and to produce large photocurrent responses. So, with this aim, we introduced modifications in the flavylium backbone such as the so-called styrylflavylium and/or naphtoflavylium able to reduce the HOMO–LUMO energy gap of the sensitizer. We prepared and assembled all the DSSC’s components and fully characterized their photovoltaic performances. Furthermore, photophysical properties were investigated with absorption transient spectroscopy. This work opens new possibility to develop new class of sensitizers synthetic analogues of natural anthocyanins.
We gratefully acknowledge PON – Industria 2007-2013: Progetto FotoRiduCO2 (prot. PON01_02257), ENERGETIC (prot. PON02_00355_3391233) and TESEO (prot. PON02_00153_2939517). Furthermore this research was financial supported by “EFOR” Project financed by CNR and by Project “SAGRO” financed by Regione Siciliana (Assessorato Regionale Attività Produttive progetti PO FESR 2007/2013 linea d’intervento 4.1.1.1). This work was also supported by Fundação para a Ciência e Tecnologia through the National Portuguese NMR Network, grant PEst- C/EQB/LA0006/2011 and project PTDC/QUI-QUI/119932/2010.
[1] Pina, F.; Melo, M. J.; Laia, C. A. T.; Parola, A. J.; Lima, J. C. Chemistry and applications of flavylium compounds: a handful of colours. Chem. Soc. Rev. 2011, 41, 869. [2] Calogero, G.; Sinopoli, A.; Citro, I.; Di Marco, G.; Petrov, V.; Diniz, A. M.; Parola, A. J.; Pina, F. Synthetic analogues of anthocyanins as sensitizers for dye-sensitized solar cells, Photochem. Photobiol. Sci. 2013, 12, 883. Cover picture.
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