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A Blue Zinc Complex of a Dioxobilin‐Type Pink Chlorophyll Catabolite Exhibiting Bright Chelation‐Enhanced Red Fluorescence
Author(s) -
Li Chengjie,
Podewitz Maren,
Kräutler Bernhard
Publication year - 2021
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100206
Subject(s) - chemistry , chelation , fluorescence , zinc , solvent , acetonitrile , photochemistry , nuclear chemistry , inorganic chemistry , organic chemistry , physics , quantum mechanics
In senescent fall leaves and in ripening fruit, colorless phyllobilins (PBs) accumulate from breakdown of chlorophyll, from which yellow PBs (phylloxanthobilins) and pink colored PBs (phylloroseobilins) arise in some leaves. The first described PBs were formyloxobilin‐type PBs, but dioxobilin‐type PBs also occur naturally. Here we report the synthesis and characterization of the blue Zn(II) complex of a dioxobilin‐type pink PB, which chelates a Zn(II) ion fast and tightly in an effectively tridentate manner. The optically active Zn complex featured bright chelation enhanced red fluorescence and exhibited strikingly differing spectral properties in methanol and in acetonitrile. Computational studies based on DFT‐calculations gave detailed insights into low energy structures of the Zn complex in both solvents and provided support for the proposed role of solvent in the coordination sphere of the bound Zn(II) ion.