Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• reaction; optoelectronic properties; S,N-heteroacene; structure–property relationship; Introduction Thienoacenes and related S,N-heteroacenes have been developed to important π-conjugated systems mainly for application as p-type semiconductor in organic electronic devices with excellent results [1][2][3

• [22][27], organic field-effect transistors [28], or sensors [23]. The interesting structure–property relationships of the S,N-heteroacene series inspired as well theoretical work. In this respect, De Simone et al. computed electronic spectra of the neutral, charged radical cationic, and dicationic

• reacted with o-iodonitrobenzene (17) and Pd[PPh3]4 as catalyst in DMF to give 2,5-bis(2-nitrophenyl)thieno[3,2-b]thiophene (21) in 86% yield. Subsequent Cadogan cyclization with triethyl phosphite under reflux gave hexacyclic S,N-heteroacene 22 in 38% yield which reflects a benzannulated SN4' system with