TY - JOUR
T1 - Thiophene-fused naphthalene diimides
T2 - New building blocks for electron deficient p-functional materials
AU - Takimiya, Kazuo
AU - Nakano, Masahiro
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Numbers 23245041, 15H02196, and 15K13775, and the Strategic Promotion of Innovative Research and Development from the Japan Science and Technology Agency. The authors also thank collaborators, Mr. Y. Fukutomi, Prof. J.-Y. Hu, Dr. K. Nakano, Dr. K. Tajima, Prof. E. Zhou, Dr. Y. Wang, Prof. T. Michinobu, Prof. T. Mori, Dr. W. Chen, Prof. Q. Zhang, and Mr. J. Hamonnet, for their contribution to the experimental work as well as fruitful discussions.
Funding Information:
Masahiro Nakano received his doctoral degree from Hiroshima University in 2013 under the supervision of Prof. Kazuo Takimiya. He was a JSPS Research Fellowship for Young Scientists from 2013 to 2015. Currently, he is working at the RIKEN Center for Emergent Matter Science (CEMS) as a special postdoctoral researcher (SPDR). His research interest is the synthesis of organic semiconducting materials with strong electron affinity and their application.
Publisher Copyright:
© 2018 The Chemical Society of Japan.
PY - 2018
Y1 - 2018
N2 - Development of novel p-conjugated building blocks that can be integrated into molecular or macromolecular systems is key to the evolution of new superior organic semiconductors utilized as the active materials in organic electronics devices such as organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and organic thermoelectric (TE) devices. This review affords a brief overview of thiophene-fused naphthalene diimide (NDI), namely naphtho[2,3-b:6,7-b]dithiophene diimide (NDTI) and naphtho[2,3-b]thiophene diimide (NTI), recently developed as novel electron deficient building blocks for n-type and ambipolar organic semiconductors. These thiophene-fused NDI building blocks had not been known until 2013 owing to their synthetic difficulty; more precisely, the difficulty in attaching fused-thiophene ring(s) on the NDI core. We have successfully established a thiophene-annulation reaction on ethyne-substituted NDI derivatives, which allows us to elaborate various NDTI and NTI derivatives. The key features of these building blocks are low-lying energy levels of lowest unoccupied molecular orbitals (LUMO, 3.84.1 eV below the vacuum level) and easy functionalizability of the thiophene positions, which allows their derivatives and polymers to conjugate efficiently with additional p- and comonomer units. These features make the NDTI- and NTIderivatives and polymers promising n-type and ambipolar materials for OFETs and acceptors for OPVs. In fact, various useful materials have already been derived from the NDTI and NTI building blocks: air-stable n-type small molecules and polymers with high electron mobility (30.8 cm2V11 s11), ambipolar oligomers and polymers with well-balanced hole and electron mobilities, doped n-type semiconductors affording bulk conductors applicable to n-type TE materials, and electron acceptor molecules and polymers for OPVs showing promising power conversion efficiencies of up to 9%. These impressive and diversified device performances testify the usefulness of thiophene-fused NDI building blocks in the development of new electron deficient p-functional materials.
AB - Development of novel p-conjugated building blocks that can be integrated into molecular or macromolecular systems is key to the evolution of new superior organic semiconductors utilized as the active materials in organic electronics devices such as organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and organic thermoelectric (TE) devices. This review affords a brief overview of thiophene-fused naphthalene diimide (NDI), namely naphtho[2,3-b:6,7-b]dithiophene diimide (NDTI) and naphtho[2,3-b]thiophene diimide (NTI), recently developed as novel electron deficient building blocks for n-type and ambipolar organic semiconductors. These thiophene-fused NDI building blocks had not been known until 2013 owing to their synthetic difficulty; more precisely, the difficulty in attaching fused-thiophene ring(s) on the NDI core. We have successfully established a thiophene-annulation reaction on ethyne-substituted NDI derivatives, which allows us to elaborate various NDTI and NTI derivatives. The key features of these building blocks are low-lying energy levels of lowest unoccupied molecular orbitals (LUMO, 3.84.1 eV below the vacuum level) and easy functionalizability of the thiophene positions, which allows their derivatives and polymers to conjugate efficiently with additional p- and comonomer units. These features make the NDTI- and NTIderivatives and polymers promising n-type and ambipolar materials for OFETs and acceptors for OPVs. In fact, various useful materials have already been derived from the NDTI and NTI building blocks: air-stable n-type small molecules and polymers with high electron mobility (30.8 cm2V11 s11), ambipolar oligomers and polymers with well-balanced hole and electron mobilities, doped n-type semiconductors affording bulk conductors applicable to n-type TE materials, and electron acceptor molecules and polymers for OPVs showing promising power conversion efficiencies of up to 9%. These impressive and diversified device performances testify the usefulness of thiophene-fused NDI building blocks in the development of new electron deficient p-functional materials.
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U2 - 10.1246/bcsj.20170298
DO - 10.1246/bcsj.20170298
M3 - Article
AN - SCOPUS:85040609494
SN - 0009-2673
VL - 91
SP - 121
EP - 140
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 1
ER -