Bowl-Shaped Anthracene-Fused Antiaromatic Ni(II) Norcorrole: Synthesis, Structure, Assembly with C 60 , and Photothermal Conversion.

Autor: Wang K; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi, 464-8603, Japan., Ghosh A; Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo, 192-0397, Japan., Shimizu D; Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan., Takano H; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi, 464-8603, Japan., Ishida M; Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo, 192-0397, Japan.; PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama, 332-0012, Japan., Kishi R; Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka, 560-8531, Japan., Shinokubo H; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi, 464-8603, Japan.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Oct 30, pp. e202419289. Date of Electronic Publication: 2024 Oct 30.
DOI: 10.1002/anie.202419289
Abstrakt: The synthesis of bowl-shaped antiaromatic molecules is challenging because the molecular distortion further destabilizes these already inherently reactive molecules. Here, we report the synthesis and properties of bowl-shaped fused anthrylnorcorroles that exhibit near-infrared (NIR) absorption reaching 1900 nm. The oxidation of meso-anthryldibromodipyrrin provides fused anthryldibromodipyrrin, which was converted to the fused mono- and bisanthrylnorcorroles through Ni(0)-mediated intramolecular coupling with a bis(dibromodipyrrin) Ni(II) complex. Single-crystal X-ray diffraction analyses revealed bowl-shaped structures for the fused mono- and bisanthrylnorcorroles, which enables them to act as suitable receptors for C 60 with bonding constants of 2.89×10 3  M -1 and 1.59×10 3  M -1 , respectively. The formation of a 1 : 1 complex between the fused monoanthrylnorcorrole and C 60 was confirmed by single-crystal X-ray diffraction analysis. The effective expansion of the π-conjugation through the triple fusion of the norcorrole with the anthracene units substantially enhances the near-infrared absorption bands, which endows these anthrylnorcorroles with effective photothermal conversion.
(© 2024 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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