Metal phthalocyanine derivatives as promising stable blue dyes for DSSC

Giovanna Pennesi^a, Gloria Zanotti^a, Aldo Amore Bonapasta^a, Giuseppe Mattioli^a, Nicola Angelini^a, Annamaria Paoletti^a, Gentilina Rossi^a, Daniela Caschera^b, Luisa De marco^c, Giuseppe Gigli^d

^aISM - CNR, Via Salaria km 29.500, Monterotondo Scalo (Rm), 00015, Italy

^bISMN - CNR, Via Salaria km 29.500, Monterotondo Scalo (Rm), 00015, Italy

^cIIT - Center for Biomolecular Nanotechnologies, Via Barsanti, Arnesano (Le), 73010, Italy

^dNANO - CNR, c/o Distretto Tecnologico, Via Arnesano 16, Lecce, 73100, Italy

International Conference on Hybrid and Organic Photovoltaics
Proceedings of International Conference on Hybrid and Organic Photovoltaics 2015 (HOPV15)

Roma, Italy, 2015 May 11th - 13th

Organizer: Filippo De Angelis

Poster, Gloria Zanotti, 207
Publication date: 5th February 2015

The absorption properties of p-extended macrocycles such as porphyrins and phthalocyanines have been intensively applied to the light -harvesting process related to organic photovoltaics, with particular focus on Dye-Sensitized Solar Cells¹. Even if in the last few years new emerging materials have shown very promising results in terms of efficiencies, it is still extremely important to study and test new dyes because of their potential application in building-integrated-photovoltaics. In particular, no blue or green dye have yet shown an outstanding stability once exposed to thermal stress and UV irradiation into the device. Phthalocyanines are of course great candidates because of their great chemical stability and high molar extinction coefficients (e> 10⁵) and these properties justify the intensive study still carried on these molecules. Amongst them an interesting sterically hindered push-pullstructure, having a record efficiency value of 6.4%² has been prepared and published. It is well known that the metal centers of these macrocyclic compounds can affect their absorption peaks, their HOMO/LUMO energy values as well as their possible charge transfer properties in a DSSC device. In this context we have chosen to investigate the performances of dyes possessing the same molecular structure but different central metal ions, and in particular we focused on copper derivatives, because of their extremely high stability and color intensity. We have synthesized the 9(10),16(17),23(24)-tri-ter-butyl-2-[acetynyl-(4-carboxy)phenyl]phthalocyaninato copper complex and its related free base and then investigated their optical and electrochemical properties. Very surprisingly, even for the copper derivative we have measured a considerable fluorescence decay that should be in principle almost completely depleted due to the spin-orbital interaction arising from its d⁹ electronic configuration. The photovoltaic performances as well as IPCE measurements will be presented for both the molecules and compared with those of the zinc derivative⁴ that has recently reached efficiency values around 2%.
General structure of target molecules (left) TiO2 sensitization with the blue copper derivative (right)
1) Walter, M. G.; Rudine, A. B.; Wamser, C. C. Porphyrins and phthalocyanines in solar photovoltaic cells. J. Porphyrins Phthalocyanines, 2010, 14 (09), 759-792. 2) Ikeuchi, T.; Nomoto, H.; Masaki, N.; Griffith, M. J.; Mori, S.; Kimura, M. Molecular engineering of zinc phthalocyanine sensitizers for efficient dye-sensitized solar cells. Chem Commun., 2014, 50, 1941-1943. 3) a) Li, L.-L.; Diau, E. W.-G. Porphyrin-sensitized solar cells. Chem. Soc. Rev., 2013, 42, 291-304. b) Yella, A.; Lee, H. W.; Tsao H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.; Zakeeruddin S. M.; Grätzel, M. Porphyrin-Sensitized Solar Cells with Cobalt (II/III)–Based Redox Electrolyte Exceed 12 Percent Efficiency. Science, 2011, 334, 629-634. 4) Zanotti,G.; Angelini, N.; Paoletti,A. M.; Pennesi,G.; Rossi, G.; Amore Bonapasta, A.; Mattioli,G.; Di Carlo, A.; Brown, T. M.; Lembo, A.; Reale A. Synthesis of a novel unsymmetrical Zn(II) phthalocyanine bearing a phenyl ethynyl moiety as sensitizer for dye-sensitized solar cells. Dalton Trans., 2011, 40, 38-40.

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