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Near-infrared fluorescein dyes containing a tricoordinate boron atom.

ABSTRACT: Bora-fluoresceins (BFs), fluorescein analogues containing a tricoordinate boron atom instead of an oxygen atom at the 10-position of the fluorescein skeleton, were synthesized as a new family of fluorescein analogues. The deprotonated BFs exhibited absorption and fluorescence in the near-infrared region, which were significantly red-shifted relative to those of hitherto-known heteroatom-substituted fluorescein analogues on account of the orbital interaction between the tricoordinate boron atom and the fluorescein skeleton. BFs also showed multi-stage changes resulting from a Lewis acid-base equilibrium at the boron center in combination with a Brønsted acid-base equilibrium at the phenolic hydroxy group.

SUBMITTER: Ando N

PROVIDER: S-EPMC6764465 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Near-infrared fluorescein dyes containing a tricoordinate boron atom.

Ando Naoki N Soutome Hiroki H Yamaguchi Shigehiro S

Chemical science 20190703 33

Bora-fluoresceins (<b>BF</b>s), fluorescein analogues containing a tricoordinate boron atom instead of an oxygen atom at the 10-position of the fluorescein skeleton, were synthesized as a new family of fluorescein analogues. The deprotonated <b>BF</b>s exhibited absorption and fluorescence in the near-infrared region, which were significantly red-shifted relative to those of hitherto-known heteroatom-substituted fluorescein analogues on account of the orbital interaction between the tricoordinat ...[more]

PMID: 31588332

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