Fused Aromatic and Antiaromatic Smaragdyrin Dimers.

Autor: Liu Y; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Tanaka T; Department of Chemistry, Graduate School of Science, Kyoto, University, Sakyo-ku, 606-8502, Kyoto, Japan., Shimizu D; Department of Chemistry, Graduate School of Science, Kyoto, University, Sakyo-ku, 606-8502, Kyoto, Japan., Rao Y; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Xu L; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Yin B; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Zhou M; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Song J; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China., Osuka A; Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 02; Vol. 63 (49), pp. e202408478. Date of Electronic Publication: 2024 Jul 15.
DOI: 10.1002/anie.202408478
Abstrakt: Singly-linked aromatic [22]smaragdyrin BF 2 complex dimer was synthesized by the reductive coupling of 16-brominated [22]smaragdyrin BF 2 complex, which was oxidized to a stable diradical with PbO 2 . As the first example of fused smaragdyrin dimer, a fused [22]smaragdyrin BF 2 complex dimer was synthesized by the oxidation of a CuCl-BF 2 complex dimer with FeCl 3 and subsequent reduction with NaBH 4 . After removal of the BF 2 group, the singly-linked and fused aromatic dimers were oxidized to the corresponding antiaromatic [20]smaragdyrin free base dimers. The first oxidation and reduction potentials of these dimers are split depending upon the intramolecular electronic interactions, which are larger for the fused dimers. Despite the large electronic interactions, the aromatic and antiaromatic characters are well preserved in the fused dimers.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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