Tetraaryl ZnII Porphyrinates Substituted at ?-Pyrrolic Positions as Sensitizers in Dye-Sensitized Solar Cells: A Comparison with meso-Disubstituted Push-Pull ZnII Porphyrinates (Articolo in rivista)

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  • Tetraaryl ZnII Porphyrinates Substituted at ?-Pyrrolic Positions as Sensitizers in Dye-Sensitized Solar Cells: A Comparison with meso-Disubstituted Push-Pull ZnII Porphyrinates (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.201300219 (literal)
Alternative label
  • Di Carlo, Gabriele and Orbelli Biroli, Alessio and Pizzotti, Maddalena and Tessore, Francesca and Trifiletti, Vanira and Ruffo, Riccardo and Abbotto, Alessandro and Amat, Anna and De Angelis, Filippo and Mussini, Patrizia R. (2013)
    Tetraaryl ZnII Porphyrinates Substituted at ?-Pyrrolic Positions as Sensitizers in Dye-Sensitized Solar Cells: A Comparison with meso-Disubstituted Push-Pull ZnII Porphyrinates
    in Chemistry - A European Journal
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Di Carlo, Gabriele and Orbelli Biroli, Alessio and Pizzotti, Maddalena and Tessore, Francesca and Trifiletti, Vanira and Ruffo, Riccardo and Abbotto, Alessandro and Amat, Anna and De Angelis, Filippo and Mussini, Patrizia R. (literal)
Pagina inizio
  • 10723 (literal)
Pagina fine
  • 10740 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://dx.doi.org/10.1002/chem.201300219 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 19 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 32 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • [a] Dr. G. Di Carlo, Prof. M. Pizzotti, Dr. F. Tessore, Prof. P. R. Mussini Dipartimento di Chimica dell?Universit? degli Studi di Milano Unit? di Ricerca dell?INSTM Via C. Golgi 19, 20133 Milano (Italy) Fax: (+39) 02-503-14405 E-mail: maddalena.pizzotti@unimi.it [b] Dr. A. Orbelli Biroli Istituto di Scienze e Tecnologie Molecolari del CNR (CNR-ISTM) Via C. Golgi 19, 20133 Milano (Italy) [c] Dr. V. Trifiletti, Dr. R. Ruffo, Prof. A. Abbotto Department of Materials Science Solar Energy Research Center MIB-SOLAR and INSTM Research Unit, University of Milano Bicocca Via Cozzi 53, 20125 Milano (Italy) [d] Dr. A. Amat, Dr. F. De Angelis Computational Laboratory for Hybrid/Organic Photovoltaics (CLHYO) Istituto di Scienze e Tecnologie Molecolari del CNR (CNR-ISTM) Via Elce di Sotto 8, 06123 Perugia (Italy) (literal)
Titolo
  • Tetraaryl ZnII Porphyrinates Substituted at ?-Pyrrolic Positions as Sensitizers in Dye-Sensitized Solar Cells: A Comparison with meso-Disubstituted Push-Pull ZnII Porphyrinates (literal)
Abstract
  • A facile and fast approach, based on microwave-enhanced Sonogashira coupling, has been employed to obtain in good yields both mono- and, for the first time, disubstituted push-pull ZnII porphyrinates bearing a variety of ethynylphenyl moieties at the ?-pyrrolic position(s). Furthermore, a comparative experimental, electrochemical, and theoretical investigation has been carried out on these ?-mono- or disubstituted ZnII porphyrinates and meso-disubstituted push-pull ZnII porphyrinates. We have obtained evidence that, although the HOMO-LUMO energy gap of the meso-substituted push-pull dyes is lower, so that charge transfer along the push-pull system therein is easier, the ?-mono- or disubstituted push-pull porphyrinic dyes show comparable or better efficiencies when acting as sensitizers in DSSCs. This behavior is apparently not attributable to more intense B and Q bands, but rather to more facile charge injection. This is suggested by the DFT electron distribution in a model of a ?-monosubstituted porphyrinic dye interacting with a TiO2 surface and by the positive effect of the ? substitution on the incident photon-to-current conversion efficiency (IPCE) spectra, which show a significant intensity over a broad wavelength range (350-650 nm). In contrast, meso-substitution produces IPCE spectra with two less intense and well-separated peaks. The positive effect exerted by a cyanoacrylic acid group attached to the ethynylphenyl substituent has been analyzed by a photophysical and theoretical approach. This provided supporting evidence of a contribution from charge-transfer transitions to both the B and Q bands, thus producing, through conjugation, excited electrons close to the carboxylic anchoring group. Finally, the straightforward and effective synthetic procedures developed, as well as the efficiencies observed by photoelectrochemical measurements, make the described ?-monosubstituted ZnII porphyrinates extremely promising sensitizers for use in DSSCs. (literal)
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