Near-infrared fluorescein dyes containing a tricoordinate boron atom

Bora-fluoresceins ( BF 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 BF s exhibited absorption and fluorescence in the near-infrared...

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Published inChemical science (Cambridge) Vol. 1; no. 33; pp. 7816 - 7821
Main Authors Ando, Naoki, Soutome, Hiroki, Yamaguchi, Shigehiro
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.09.2019
Royal Society of Chemistry
Subjects
Boron
Chemistry
Chemistry, Multidisciplinary
Crystallography
Fluorescein
Fluorescence
Lewis acid
Near infrared radiation
Physical Sciences
Science & Technology
RED
POLYMERS
RHODAMINE DYES
POLYCYCLIC AROMATICS
BUILDING-BLOCKS
WAVELENGTH
HEAVY-CHALCOGEN ANALOGS
SCAFFOLDS
SUBSTITUTED XANTHENE DYES
PROBES
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Summary:Bora-fluoresceins ( BF 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 BF 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 tricoordinate boron atom and the fluorescein skeleton. BF s 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. Tricoordinate boron imparts near-infrared absorption/emission and unusual multi-stage changes in the photophysical properties to fluorescein dyes.
Bibliography:CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
and
1913398
1913399
Electronic supplementary information (ESI) available: Experimental procedures, spectral data, details of the computational studies, and crystallographic data for
10.1039/c9sc02314c
BF3
BF2
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc02314c