Synthesis and Optical Properties of L-Shaped Dinaphthofluoresceins with Two Peripheral Hydroxy Groups

V-shaped xanthene dyes capable of predicting absorption and emission wavelengths are described. These dyes were synthesized by bridging a xanthene ring and an aryl moiety of fluorescein through ether covalent bonds. These dyes showed longer absorption and emission wavelengths than those of the parent fluorescein. Furthermore, substituents introduced on the aryl moiety mainly affected the lowest unoccupied molecular orbital energy level of the molecule. Therefore, the Hammett substituent constants could be used to predict the absorption and emission wavelengths of the compound.

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Synthesis and Properties of V-Shaped Xanthene Dyes with Tunable and Predictable Absorption and Emission Wavelengths

Yamagami

Kiyotaki

Wakabayashi

et al. 2022

J. Org. Chem.

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Total Syntheses of FR-901235, Auxarthrones A–D, and Lamellicolic Anhydride

et al. 2020

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In our previous study, an unusual rearrangement reaction was discovered whereby dinaphthyl ketones with three hydroxy groups at restricted positions were transformed into a phenalenone ring and a benzene ring. Using the rearrangement as a key reaction, the first total syntheses of FR-901235 and auxarthrones A–D from an unstable triketone common intermediate are described. Furthermore, lamellicolic anhydride was synthesized from the triketone. This conversion is part of the putative biosynthetic pathway and was achieved experimentally for the first time.

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An Alternative Approach to the Development of Near-Infrared Fluorescent Dyes Based on Fluorescein

et al. 2021

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In xanthene dyes the upper aryl moiety is often a benzene ring, but in this work an L-shaped dibenzoxanthene dye (4) was synthesized with a five-membered (benz)imidazole ring as the upper aryl moiety. Although 4 was designed with the π-face of the dibenzoxanthene and the π-plane of the aryl moiety as coplanar, the reactivity of the compound at the triaryl carbon was quite high and easily attacked by solvent, such as methanol. The consequent discoloration is caused not only by the external exposure of the triaryl carbon, but also by the greatly reduced LUMO level and increased reactivity to nucleophilic attack when the π-system of the xanthene ring is expanded. The introduction of the 2,6-dimethylphenyl group was found to be effective to avoid nucleophilic attack by solvent. A compound, labeled 9c, with a 2,6-dimethylphenyl group as the aryl moiety, had sufficient stability to solvent, an emission maximum at 828 nm in DMF, and a fluorescence quantum yield of 8%.

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Synthesis and Optical Properties of L-Shaped Dinaphthofluoresceins with Two Peripheral Hydroxy Groups

Cited by 3 publications

References 17 publications

Synthesis and Properties of V-Shaped Xanthene Dyes with Tunable and Predictable Absorption and Emission Wavelengths

Synthesis and Properties of V-Shaped Xanthene Dyes with Tunable and Predictable Absorption and Emission Wavelengths

Total Syntheses of FR-901235, Auxarthrones A–D, and Lamellicolic Anhydride

An Alternative Approach to the Development of Near-Infrared Fluorescent Dyes Based on Fluorescein

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