Abstract
A new π-extended naphthalene diimide with one fused-thiophene ring, naphtho[2,3-b]thiophene diimide (NTI), was synthesized.
Highlights
A new p-extended naphthalene diimide with one fused-thiophene ring, naphtho[2,3-b]thiophene diimide (NTI), was synthesized
We have recently reported a cNDI with two fused-thiophene rings, i.e., naphtho[2,3-b:6.7-b0]dithiophene diimide (NDTI, Fig. 1), which has been proved useful in developing NDTI-based a Emergent Molecular Function Research Group, RIKEN Center for Emergent Mater Science (CEMS), 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan
We here first report the synthesis and characterization of NTI, and its utilization to develop a range of NTI-terminated molecular architectures, such as the dimer [2], NTI-based triads [3, 4], and a dendritic trimer with a benzene core [5], which acted as n-type organic semiconductors (Fig. 1)
Summary
Naphtho[2,3-b]thiophene diimide (NTI): a monofunctionalisable core-extended naphthalene diimide for electron-deficient architectures†. A new p-extended naphthalene diimide with one fused-thiophene ring, naphtho[2,3-b]thiophene diimide (NTI), was synthesized. Taking advantage of its mono-functionalisability, NTI was incorporated into various ‘‘NTI-terminated’’ p-conjugated architectures, which functioned as n-type organic semiconductors for field-effect transistors and solar cells. We here first report the synthesis and characterization of NTI, and its utilization to develop a range of NTI-terminated molecular architectures, such as the dimer [2], NTI-based triads [3, 4], and a dendritic trimer with a benzene core [5], which acted as n-type organic semiconductors (Fig. 1). For the synthesis of 1, we first prepared N,N0-dioctyl-2-(trimethylsilyl)ethynyl-NDI (7a) from the corresponding 2-bromo-NDI (6a, see the ESI†). As depicted in Scheme 1, 7a was effectively converted into the NTI structure with a trimethylsilyl (TMS) group at the thiophene a-position (8a) in 65% isolated yield via a sodium sulphide-promoted thiophene annulation reaction.
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