Synthesis and spectral properties of non-symmetrical red and near IR emitter dibenzoBODIPYs

[Display omitted] •Synthesis of non-symmetrical benzoBODIPY.•Cross-condensation of diketones.•Red NIR emitters.•pH responsive dyes. New symmetrical and non-symmetrical benzoBODIPYs have been synthesized from diketones. For the two series the 3 and 5 positions have been substituted by different aroma...

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Bibliographic Details
Published in:Tetrahedron letters 2018-03, Vol.59 (10), p.878-881
Main Authors: Khelladi, Mustapha, Leclerc, Nicolas, Jacquemin, Denis, De Nicola, Antoinette, Ulrich, Gilles
Format: Article
Language:English
Subjects:
BenzoBODIPY
Chemical Sciences
Fluorophore
Red emitters
Synthesis
TD-DFT
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Summary:[Display omitted] •Synthesis of non-symmetrical benzoBODIPY.•Cross-condensation of diketones.•Red NIR emitters.•pH responsive dyes. New symmetrical and non-symmetrical benzoBODIPYs have been synthesized from diketones. For the two series the 3 and 5 positions have been substituted by different aromatic rings and onto benzo sub-units different groups have been introduced. The methodology of diketones self-condensation provides symmetrical dyes. By cross-condensation reaction, these positions can be differentiated and specific functions connected to the desired positions. These molecules have been fully characterized and their optical properties analyzed by both experimental and theoretical means. They are red to NIR emitters with a range of emission from 679 to 780 nm in CH2Cl2. They show maxima of absorption between 651 nm and 732 nm, strong ε of around 100,000 M−1 cm−1 and quite good quantum yields from 16% to 75%. The thienyl moiety on α-positions of the nitrogens generates the highest red shifts. Meanwhile dimethylamino groups in the same positions bring, besides chemical properties, proton sensitive dyes. The bromine atom onto the dibenzo sub-units exhibits good reactivity through Sonogashira coupling reactions. This approach provides multifunctional red to NIR dyes with endless possibilities of combination of chemical properties.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.01.047