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Efficient Synthesis of a Regioregular Oligothiophene Photovoltaic Dye Molecule, MK‐2, and Related Compounds: A Cooperative Hypervalent Iodine and Metal‐Catalyzed Synthetic Route
Author(s) -
Dohi Toshifumi,
Yamaoka Nobutaka,
Nakamura Shota,
Sumida Kohei,
Morimoto Koji,
Kita Yasuyuki
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203503
Subject(s) - hypervalent molecule , stille reaction , iodine , yield (engineering) , materials science , regioselectivity , catalysis , combinatorial chemistry , acceptor , iodide , photochemistry , chemistry , organic chemistry , physics , metallurgy , condensed matter physics
We have successfully established an efficient route to the core structure of donor–acceptor head‐to‐tail (H–T)‐linked regioregular oligothiophenes, which includes the following key synthetic steps, that is, hypervalent iodine induced direct and regioselective coupling of thiophenes and the use of the obtained bithiophenes as excellent coupling substrates for the Suzuki and Stille couplings. The versatility of this new approach is highlighted in the dramatic improvement of the yield (ca. 59 % overall yield) of MK‐2, a high‐performance organic dye, for photovoltaic applications.