NDLI: Enhancement of Light Absorption Ability of Synthetic Chlorophyll Derivatives by Conjugation with a Difluoroboron Diketonate Group

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Enhancement of Light Absorption Ability of Synthetic Chlorophyll Derivatives by Conjugation with a Difluoroboron Diketonate Group

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kitagawa, Yuichi Tamiaki, Hitoshi Kinoshita, Yusuke
Description	Author Affiliation: Kinoshita Y ( Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga, 525-8577, Japan.); Kitagawa Y ( Division of Materials Chemistry, Faculty of Engineering, Hokkaido University, North-13 West-8, Kita-ku, Sapporo, Hokkaido, 060-8628, Japan.); Tamiaki H ( Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga, 525-8577, Japan. tamiaki@fc.ritsumei.ac.jp.)
Abstract	The enhancement of the light absorption ability of synthetic chlorophyll derivatives is demonstrated. Chlorophyll derivatives directly conjugated with a difluoroboron 1,3-diketonate group at the C3 position were synthesized from methyl pyropheophorbide-d through Barbier acylmethylation of the C3-formyl moiety, oxidation of the C3-carbinol, and difluoroboron complexation of the diketonate. Electronic absorption spectra in a diluted solution showed that the synthetic conjugates gave an absorption band at λ=400–500 nm, with a Qy band shifted to a longer wavelength of λ≈700 nm. DFT calculations demonstrated that the absorption bands and redshifts were ascribable to the coupling of the LUMO of chlorin with that of the difluoroboron diketonate moiety. The introduction of a pyrenyl group at the $C3^{3}-position$ of the conjugate afforded an additional charge-transfer band over λ=500 nm, producing a pigment that bridged the green gap in standard chlorophylls.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	29
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-07-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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