Carbohydrates and BODIPYs: access to bioconjugatable and water-soluble BODIPYs

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Conversion of F-BODIPYs to Cl-BODIPYs: enhancing the reactivity of F-BODIPYs.

A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the overall conversion of F-BODIPYs to O- and C-BODIPYs in high overall yields using a mild one-pot procedure. This route enables F-BODIPYs to be transformed into derivatives that are...

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Meso enamine substituted BODIPYs.

Different enamines were introduced at the meso position of the BODIPY by catalyst free oxidation of tert-amines and in situ cross coupling with 8-chloro BODIPY. The reaction conditions were optimized to achieve better yields. The reaction works well with aliphatic tert-amines bearing an N-(CH-CH-) backbone. The N-alkyl substituents perturb the optical properties of enamine substituted BODIPYs.

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Axially chiral BODIPYs.

The synthesis and resolution of a class of chiral organic fluorophores, axially chiral 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (Ax*-BODIPY), is described. Ax*-BODIPYs were prepared through a modular synthesis combined with a late stage Heck functionalisation. Resolution was achieved by preparative chiral HPLC. Absolute stereochemical assignment was performed by comparison of experimental EC...

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S2 emission from chemically modified BODIPYs.

Novel boron dipyrromethene (BODIPY) derivatives having significant absorption and emission in the longer wavelength region were synthesized. BODIPY showed anomalous S(2) emission from the second excited (S(2)) state at shorter wavelength. The photodynamics of the S(2) state was investigated by fluorescence up-conversion and transient absorption spectroscopic measurements. The decay time of the ...

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Synthesis and regioselective functionalization of perhalogenated BODIPYs.

Three perhalogenated BODIPYs (1b-3b), bearing chloro and bromo groups at all carbon positions, were synthesized and characterized. The reactivity of BODIPY 3b was investigated under Stille cross-coupling reactions, and single crystal X-ray analysis was used to confirm the regioselectivity of the reactions. Further substitution at the boron atom produced nona-functionalized BODIPYs 7a,b, which s...

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ژورنال

عنوان ژورنال: Pure and Applied Chemistry

سال: 2019

ISSN: 1365-3075,0033-4545

DOI: 10.1515/pac-2019-0204