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Article

Tuning the Acceptor Unit of Push–Pull Porphyrazines for Dye-Sensitized Solar Cells

1
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
2
Instituto Madrileño de Estudios Avanzados (IMDEA)-Nanociencia, c/ Faraday, 9, Cantoblanco, 28049 Madrid, Spain
3
Laboratoire de Réactivité et Chimie des Solides, Université de Picardie Jules Verne, CNRS UMR7314, Hub de L’énergie, 15 rue Baudelocque, 80039 Amiens, France
*
Authors to whom correspondence should be addressed.
Academic Editors: Chen-Yu Yeh and Soji Shimizu
Molecules 2021, 26(8), 2129; https://doi.org/10.3390/molecules26082129
Received: 18 February 2021 / Revised: 19 March 2021 / Accepted: 30 March 2021 / Published: 7 April 2021
(This article belongs to the Special Issue Phthalocyanines and Porphyrins)
A family of four push–pull porphyrazines of A3B type, where each unit A contains two peripheral propyl chains and the unit B is endowed with a carboxylic acid, were prepared. The carboxylic acid was attached to the β-position of the pyrrolic unit, either directly (Pz 10), or through cyanovinyl (Pz 11) and phenyl (Pz 7) groups. The fourth Pz (14) consisted in a pyrazinoporphyrazine wherein the dinitrogenated heterocycle provided intrinsic donor–acceptor character to the macrocycle and contained a carboxyphenyl substituent. The direct attachment of the carboxylic acid functions and their linkers to the porphyrazine core produces stronger perturbation on the electronic properties of the macrocycle, with respect to their connection through fused benzene or pyrazine rings in TT112 and 14, respectively. The HOMO and LUMO energies of the Pzs, which were estimated with DFT calculations, show little variation within the series, except upon introduction of the cyanovinyl spacer, which produces a decrease in both frontier orbital energetic levels. This effective interaction of cyanovinyl substitution with the macrocycle is also evidenced in UV/Vis spectroscopy, where a large splitting of the Q-band indicates strong desymmetrization of the Pz. The performance of the four Pzs as photosensitizers in DSSCs were also investigated. View Full-Text
Keywords: porphyrazines; push–pull systems; amphiphilic systems; dye-sensitized solar cells; photovoltaics porphyrazines; push–pull systems; amphiphilic systems; dye-sensitized solar cells; photovoltaics
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MDPI and ACS Style

Medina, D.-P.; Fernández-Ariza, J.; Urbani, M.; Sauvage, F.; Torres, T.; Rodríguez-Morgade, M.S. Tuning the Acceptor Unit of Push–Pull Porphyrazines for Dye-Sensitized Solar Cells. Molecules 2021, 26, 2129. https://doi.org/10.3390/molecules26082129

AMA Style

Medina D-P, Fernández-Ariza J, Urbani M, Sauvage F, Torres T, Rodríguez-Morgade MS. Tuning the Acceptor Unit of Push–Pull Porphyrazines for Dye-Sensitized Solar Cells. Molecules. 2021; 26(8):2129. https://doi.org/10.3390/molecules26082129

Chicago/Turabian Style

Medina, Diana-Paola, Javier Fernández-Ariza, Maxence Urbani, Frédéric Sauvage, Tomás Torres, and M. S. Rodríguez-Morgade. 2021. "Tuning the Acceptor Unit of Push–Pull Porphyrazines for Dye-Sensitized Solar Cells" Molecules 26, no. 8: 2129. https://doi.org/10.3390/molecules26082129

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