Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization
Entity
UAM. Departamento de Química OrgánicaPublisher
Wiley-VCH VerlagDate
2019-06-04Citation
10.1002/cplu.201800631
ChemPlusChem 84.6 (2019): 673-679
ISSN
2192-6506DOI
10.1002/cplu.201800631Funded by
This work has been supported by MINECO, Spain (CTQ2017‐85393‐P and CTQ2016‐78454‐C2‐1‐R). C. H. thanks the European Social Funds and the SUR del DEC de la Generalitat de Catalunya for his predoctoral fellowships (Grant No. 2017 FI_B 00617 and 2018 FI_B1 00174)Project
Gobierno de España. CTQ2017‐85393‐P; Gobierno de España. CTQ2016‐78454‐C2‐1‐REditor's Version
https://doi.org/10.1002/cplu.201800631Subjects
Collinear functionalization; Fluorescence; Photophysics; Phthalocyanines; Singlet oxygen; QuímicaNote
This is the peer reviewed version of the following article: Revuelta‐Maza, M. A., Hally, C., Nonell, S., de la Torre, G., & Torres, T. (2019). Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization. ChemPlusChem, 84(6), 673-679, which has been published in final form at https://doi.org/10.1002/cplu.201800631. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived VersionsSupporting information for this article is available on the WWW under https://doi.org/10.1002/cplu.201800631
Rights
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimAbstract
We describe here the preparation of a series of trans-ABAB Zn(II) phthalocyanines (ZnPcs, which combine several interesting features. First, these compounds present high solubility and hindered aggregation, due to the functionalization of two facing isoindole constituents (B) of the ZnPc with bis(trifluoromethylphenyl) units. Second, the other two isoindoles (A) bear extra-annulated phthalimide units containing different substituents in the nitrogen positions, this feature results in a collinear arrangement of a variety of functional groups. Some of these collinearly functionalized ZnPcs are interesting building blocks for constructing either homo- or heteroarrays containing ZnPc units. Furthermore, the amphiphilic nature of some members of the series renders them interesting candidates for photosensitization of singlet oxygen. Photophysical studies on a model compound of the series have shown that these molecules are efficient singlet oxygen photosensitizers in both polar and apolar media, with 1O2 quantum yields (φΔ) as high as 0.74
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Google Scholar:Revuelta-Maza, Miguel A.
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Hally, Cormac
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Nonell, Santi
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Torre Ponce, Gema de la
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Torres Cebada, Tomás
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