Chemical Science
Edge Article
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Scheme
1 Synthesis of unsymmetrical dithienylated DFBT via
sequential C–H bond functionalization and synthesis of red light-
emitting dye 14.
In conclusion, we have demonstrated an unprecedented
example of selective Pd-catalyzed thienylation of FBT with
simple thiophenes via dual C–H functionalization. The reaction
proceeds under mild reaction conditions, providing a series of
unsymmetrical and symmetrical FBT–thiophene structures in
high efficiency with excellent functional group compatibility.
The reaction can also be extended to FTAZ. Application of the
method led to important and useful FBT–thiophene monomers
that can be applied in the development of high performance
photovoltaics, in particular in BHJ solar cells. Because of the
synthetic simplicity as well as the high chemo- and regio-selec-
tivity of this protocol, we believe that it should be useful for the
atom/step-economical synthesis of new FBT–thiophene based
photovoltaic materials. Further studies to extend the substrate
scope and its application in the development of photovoltaics
are underway in our laboratory and will be reported in due
course.
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Acknowledgements
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This work was nancially supported by the National Basic
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1320 | Chem. Sci., 2014, 5, 1317–1321
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