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Fluorenylporphyrins functionalized by electrochromic ruthenium units as redox-triggered fluorescence switches

Zhang, Xu; Abid, Seifallah; Shi, Limiao; Williams, J.A. Gareth; Fox, Mark A.; Miomandre, Fabien; Tourbillon, Clarisse; Audibert, Jean-Frédéric; Mongin, Olivier; Paul, Frédéric; Paul-Roth, Christine O.

Fluorenylporphyrins functionalized by electrochromic ruthenium units as redox-triggered fluorescence switches Thumbnail


Authors

Xu Zhang

Seifallah Abid

Limiao Shi

Fabien Miomandre

Clarisse Tourbillon

Jean-Frédéric Audibert

Olivier Mongin

Frédéric Paul

Christine O. Paul-Roth



Abstract

Two dyads containing tris- and tetrakis-meso-fluorenyl-substituted porphyrin and ethynylruthenium units, 1 and 2, were investigated by emission spectro-electrochemical (SEC) methods for their potential use as fluorescence switches. The ruthenium group as a potential electron donor and the porphyrin as a potential electron acceptor are connected by a phenylene bridge in 1 and by a fluorenylene bridge in 2. The new fluorenyl-linked dyad 2 was probed by UV-visible, near-infrared (NIR) and infrared (IR) absorption SEC methods, and the properties interpreted with the aid of hybrid-DFT computations, for comparison with reported data for 1. The porphyrin-based fluorescence of 1 decreased in intensity upon oxidation to 1+ and decreased further on oxidising 1+ to 12+. A much weaker change in the fluorescence intensity of 2 was observed upon oxidation to 2+ but the intensity decreased upon subsequent oxidation of 2+ to 22+. These findings contrast with data reported for some other porphyrins appended with redox-active ruthenium or iron units, where fluorescence intensities increase upon oxidation of the peripheral metal centers, but they match data reported more recently for closely related arrays. A rationale for these apparently contrasting observations is proposed.

Citation

Zhang, X., Abid, S., Shi, L., Williams, J. G., Fox, M. A., Miomandre, F., …Paul-Roth, C. O. (2019). Fluorenylporphyrins functionalized by electrochromic ruthenium units as redox-triggered fluorescence switches. Dalton Transactions, 48(31), 11897-11911. https://doi.org/10.1039/c9dt02087j

Journal Article Type Article
Acceptance Date Jul 9, 2019
Online Publication Date Jul 10, 2019
Publication Date Aug 21, 2019
Deposit Date Aug 7, 2019
Publicly Available Date Jul 10, 2020
Journal Dalton Transactions
Print ISSN 1477-9226
Electronic ISSN 1477-9234
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 48
Issue 31
Pages 11897-11911
DOI https://doi.org/10.1039/c9dt02087j

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