A Versatile Synthesis of Long-Wavelength-Excitable BODIPY Dyes from Readily Modifiable Cyclopenta[2,1-b:3,4-b′]dithiophenes

Abstract Knoevenagel condensation of a simple methylated ­borondipyrromethene (Bodipy) with 4,4′-dihexyl-4 H -cyclopenta-[2,1- b :3,4- b′ ]dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic deriv...

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Bibliographic Details
Published in:Synlett 2014-06, Vol.25 (10), p.1466-1472
Main Authors: Sutter, Alexandra, Ziessel, Raymond
Format: Article
Language:English
Subjects:
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Summary:Abstract Knoevenagel condensation of a simple methylated ­borondipyrromethene (Bodipy) with 4,4′-dihexyl-4 H -cyclopenta-[2,1- b :3,4- b′ ]dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0033-1341278