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Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole‐Transport Properties
Author(s) -
Li Yifan,
Gryn'ova Ganna,
Saenz Felipe,
Jeanbourquin Xavier,
Sivula Kevin,
Corminboeuf Clémence,
Waser Jérôme
Publication year - 2017
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.201701139
Subject(s) - hypervalent molecule , heteroatom , domino , combinatorial chemistry , nanotechnology , in silico , materials science , chemistry , reagent , ring (chemistry) , computer science , catalysis , organic chemistry , biochemistry , gene
Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid‐state and electronic properties are still challenging tasks, which slow down progress in the development of new materials. Here, we report a flexible and efficient synthesis of unprecedented heterotetracenes based on a platinum‐ and gold‐catalyzed cyclization–alkynylation domino process using EthynylBenziodoXole (EBX) hypervalent iodine reagents in the key step. The proof‐of‐principle in silico estimation of the synthesized tetracenes’ charge transport properties reveals their strong dependence on both the position and nature of the heteroatoms in the ring system. A broad range of mobility is predicted, with some compounds displaying performance potentially comparable to that of state‐of‐the‐art electronic organic materials.