TY - JOUR
T1 - Sodium sulfide-promoted thiophene-annulations
T2 - Powerful tools for elaborating organic semiconducting materials
AU - Nakano, Masahiro
AU - Takimiya, Kazuo
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Numbers 15H02196 and 16K05900.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2017/1/10
Y1 - 2017/1/10
N2 - We describe herein facile thiophene annulation reactions promoted by sodium sulfide hydrate (Na2S·9H2O) for the synthesis of acene(di)thiophenes that can be further utilized as organic semiconductors or building blocks for the elaboration of semiconducting oligomers and polymers. Sodium sulfide hydrate is an efficient source of sulfur for both the aromatic nucleophilic substitution (SNAr) reaction and the nucleophilic hydrogen substitution (SNH) reaction to give a range of electron-donating acene(di)thiophenes and an electron-deficient naphtho[2,3-b:6,7-b′]dithiophene diimide (NDTI), respectively. We also describe organic semiconducting materials on the basis of these acene(di)thiophenes and their use in organic devices, such as organic field-effect transistors and organic photovoltaics, and demonstrate that synthetic evolution is one of the keys to promoting the field of organic semiconducting materials.
AB - We describe herein facile thiophene annulation reactions promoted by sodium sulfide hydrate (Na2S·9H2O) for the synthesis of acene(di)thiophenes that can be further utilized as organic semiconductors or building blocks for the elaboration of semiconducting oligomers and polymers. Sodium sulfide hydrate is an efficient source of sulfur for both the aromatic nucleophilic substitution (SNAr) reaction and the nucleophilic hydrogen substitution (SNH) reaction to give a range of electron-donating acene(di)thiophenes and an electron-deficient naphtho[2,3-b:6,7-b′]dithiophene diimide (NDTI), respectively. We also describe organic semiconducting materials on the basis of these acene(di)thiophenes and their use in organic devices, such as organic field-effect transistors and organic photovoltaics, and demonstrate that synthetic evolution is one of the keys to promoting the field of organic semiconducting materials.
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U2 - 10.1021/acs.chemmater.6b03413
DO - 10.1021/acs.chemmater.6b03413
M3 - Review article
AN - SCOPUS:85018659253
VL - 29
SP - 256
EP - 264
JO - Chemistry of Materials
JF - Chemistry of Materials
SN - 0897-4756
IS - 1
ER -