π-Extended Pyrrole-Fused Heteropine: Synthesis, Properties, and Application in Organic Field-Effect Transistors
Dr. Weifan Wang
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorFiona Hanindita
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorYusei Tanaka
Institute for Advanced Study, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan
Search for more papers by this authorKotaro Ochiai
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorDr. Hiroyasu Sato
Rigaku Corporation, 3-9-12 Matsubara-Cho, Akishima, Tokyo, 196-8666 Japan
Search for more papers by this authorDr. Yongxin Li
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Takuma Yasuda
Institute for Advanced Study, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shingo Ito
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorDr. Weifan Wang
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorFiona Hanindita
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorYusei Tanaka
Institute for Advanced Study, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan
Search for more papers by this authorKotaro Ochiai
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorDr. Hiroyasu Sato
Rigaku Corporation, 3-9-12 Matsubara-Cho, Akishima, Tokyo, 196-8666 Japan
Search for more papers by this authorDr. Yongxin Li
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Takuma Yasuda
Institute for Advanced Study, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shingo Ito
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorGraphical Abstract
Here we report an efficient method for the synthesis of π-extended pyrrole-fused heteropine compounds and investigated their optical and electronic properties. A π-extended pyrrole-fused thiepine exhibited a “pitched π-stacking” structure in the crystal, and exhibited a high charge carrier mobility of up to 1.0 cm2 V−1 s−1 in single-crystal field-effect transistors.
Abstract
Sulfur-embedded polycyclic aromatic compounds have been used as building blocks for numerous organic semiconductors over the past few decades. While the success is based on thiophene-containing compounds, aromatic compounds that contain thiepine, a sulfur-containing seven-membered-ring arene, has been less well investigated. Here we report the synthesis and properties of π-extended pyrrole-fused heteropine compounds such as thiepine and oxepine. A π-extended pyrrole-fused thiepine exhibited a “pitched π-stacking” structure in the crystal, and exhibited a high charge carrier mobility of up to 1.0 cm2 V−1 s−1 in single-crystal field-effect transistors.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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| anie202218176-sup-0001-misc_information.pdf2.3 MB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_1c.cif443.4 KB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_3a.cif1.4 MB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_3c.cif846 KB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_4b.cif2 MB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_4c.cif1.3 MB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_5.cif718.4 KB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_6.cif433.4 KB | Supporting Information |
| anie202218176-sup-0001-SI_Compound_7.cif837 KB | Supporting Information |
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