Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

5 years ago

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

Felipe Saenz, Kevin Sivula, Yifan Li, Xavier Jeanbourquin, Clémence Corminboeuf, Jérôme Waser, Ganna Gryn'ova

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. Acenes, acenes everywhere: Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. Here, we report a flexible and efficient synthesis of heterotetracenes based on a platinum- and gold-catalyzed cyclization–alkynylation domino process using ethynylbenziodoxole (EBX) hypervalent iodine reagents in the key step, as well the in silico estimation of the synthesized tetracenes’ charge mobility.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701139