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- Title
Synthesis of Thiophene‐annulated Naphthalene Diimide‐based Small‐Molecular Acceptors via Two‐step C−H Activation.
- Authors
Matsidik, Rukiya; Takimiya, Kazuo
- Abstract
Thiophene‐annulated naphthalene diimide (NTI)‐based molecules have recently emerged as an important class of n‐type electronic materials. However, their synthesis has predominantly been achieved by Stille or Suzuki coupling reactions despite the presence of a potential C−H bond in NTI. Additionally, the synthesis of NTI or more generally mono‐functionalization of naphthalene diimide (NDI) starts with a cumbersome bromination that results in a low yield, is unselective, and requires tedious purification. We herein thus address these issues via a two‐step C−H activation: a rhodium‐catalyzed direct C−H iodinization is first presented for NDI, followed by establishing an efficient direct arylation protocol for NTI with high yield and robustness. Coupling of up to four NTI units on a benzene or pyrene core is demonstrated along with other aryl bromide substrates. All the herein reported NTI‐based small molecules showed n‐type semiconductor behavior under air.
- Subjects
NAPHTHALENE synthesis; SMALL molecules; N-type semiconductors; THIOPHENES; SUZUKI reaction; ARYL bromides
- Publication
Chemistry - An Asian Journal, 2019, Vol 14, Issue 10, p1651
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201801655