β-Fluorinated porpholactones and metal complexes: synthesis, characterization and some spectroscopic studies

Ji-Yun Hu; Zhuo-Yan Wu; Ke Chai; Zi-Shu Yang; Yin-Shan Meng; Yingying Ning; Jing Zhang; Jun-Long Zhang

doi:10.1039/C7QI00375G

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β-Fluorinated porpholactones and metal complexes: synthesis, characterization and some spectroscopic studies†

Ji-Yun Hu,

^a Zhuo-Yan Wu,

^a Ke Chai,

^b Zi-Shu Yang,

^a Yin-Shan Meng,

^a Yingying Ning,

^a Jing Zhang

*^b and Jun-Long Zhang

*^a

Author affiliations

* Corresponding authors

^a Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing, P.R. China
E-mail: Zhangjunlong@pku.edu.cn

^b College of Materials Science and Optoelectronics Technology, University of Chinese Academy of Sciences, Beijing, P. R. China
E-mail: zhangj271@ucas.ac.cn

Abstract

We describe the synthesis of β-fluorinated porpholactones by oxidation of the fluorinated C [double bond, length as m-dash] C bond of the pyrrolic subunit in porphyrin using the “RuCl₃ + Oxone®” protocol. The electron-withdrawing effects of β-fluorine on the absorption, fluorescence, phosphorescence and redox properties of the β-fluoroporpholactones were studied. A potential application of the β-fluoroporpholactones was demonstrated in sensitizing near-IR (NIR) emissive ytterbium, giving a high quantum yield (58%) and long luminescence time (525 μs) in CD₂Cl₂.

This article is part of the themed collection: Celebrating 110th Anniversary of Chemistry at Peking University

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DOI: https://doi.org/10.1039/C7QI00375G
Article type: Research Article
Submitted: 03 Jul 2017
Accepted: 21 Jul 2017
First published: 24 Jul 2017

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Inorg. Chem. Front., 2017,4, 1539-1545

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β-Fluorinated porpholactones and metal complexes: synthesis, characterization and some spectroscopic studies

J. Hu, Z. Wu, K. Chai, Z. Yang, Y. Meng, Y. Ning, J. Zhang and J. Zhang, Inorg. Chem. Front., 2017, 4, 1539 DOI: 10.1039/C7QI00375G

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Inorganic Chemistry Frontiers

β-Fluorinated porpholactones and metal complexes: synthesis, characterization and some spectroscopic studies†

Abstract

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β-Fluorinated porpholactones and metal complexes: synthesis, characterization and some spectroscopic studies

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