N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents
Naphtho[2,3-b:6,7-b′]dithiophene-4,5,9,10-tetracarboxylic diimide (NDTI) is a promising electron-deficient building block for n-type organic conductors, and the performance of NDTI-based field-effect transistors (FETs) is largely dependent on the substituents that alter the supramolecular organizati...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/8/981 |
| _version_ | 1818270149612929024 |
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| author | Masahiro Nakano Daisuke Hashizume Kazuo Takimiya |
| author_facet | Masahiro Nakano Daisuke Hashizume Kazuo Takimiya |
| author_sort | Masahiro Nakano |
| collection | DOAJ |
| description | Naphtho[2,3-b:6,7-b′]dithiophene-4,5,9,10-tetracarboxylic diimide (NDTI) is a promising electron-deficient building block for n-type organic conductors, and the performance of NDTI-based field-effect transistors (FETs) is largely dependent on the substituents that alter the supramolecular organization in the solid state and, in turn, the intermolecular orbital overlap. For this reason, the rational selection of substituent on imide nitrogen atoms and/or thiophene α-positions is the key to developing superior n-type organic semiconductors. We here report new NDTI derivatives having N-(2-cyclohexylethyl) groups. Despite their one-dimensional packing structures in the solid state regardless of the presence or absence of chlorine groups at the thiophene α-positions, their FETs show promising performance with electron mobilities higher than 0.1 cm2·V−1·s−1 under ambient conditions. We also discuss how the cyclohexylethyl groups affect the packing structure in comparison with analogous n-octyl derivatives having the same number of carbon atoms. |
| first_indexed | 2024-12-12T21:05:41Z |
| format | Article |
| id | doaj.art-fd2e40c577a040638a4ce37e05deb6e9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T21:05:41Z |
| publishDate | 2016-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fd2e40c577a040638a4ce37e05deb6e92022-12-22T00:12:01ZengMDPI AGMolecules1420-30492016-07-0121898110.3390/molecules21080981molecules21080981N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of SubstituentsMasahiro Nakano0Daisuke Hashizume1Kazuo Takimiya2Emergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, JapanMaterials Characterization Support Unit, RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, JapanEmergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, JapanNaphtho[2,3-b:6,7-b′]dithiophene-4,5,9,10-tetracarboxylic diimide (NDTI) is a promising electron-deficient building block for n-type organic conductors, and the performance of NDTI-based field-effect transistors (FETs) is largely dependent on the substituents that alter the supramolecular organization in the solid state and, in turn, the intermolecular orbital overlap. For this reason, the rational selection of substituent on imide nitrogen atoms and/or thiophene α-positions is the key to developing superior n-type organic semiconductors. We here report new NDTI derivatives having N-(2-cyclohexylethyl) groups. Despite their one-dimensional packing structures in the solid state regardless of the presence or absence of chlorine groups at the thiophene α-positions, their FETs show promising performance with electron mobilities higher than 0.1 cm2·V−1·s−1 under ambient conditions. We also discuss how the cyclohexylethyl groups affect the packing structure in comparison with analogous n-octyl derivatives having the same number of carbon atoms.http://www.mdpi.com/1420-3049/21/8/981application of naphthalene diimideorganic synthesissupramolecular chemistryorganic field-effect transistorcrystal structure |
| spellingShingle | Masahiro Nakano Daisuke Hashizume Kazuo Takimiya N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents Molecules application of naphthalene diimide organic synthesis supramolecular chemistry organic field-effect transistor crystal structure |
| title | N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents |
| title_full | N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents |
| title_fullStr | N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents |
| title_full_unstemmed | N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents |
| title_short | N,N′-Bis(2-cyclohexylethyl)naphtho[2,3-b:6,7-b′]dithiophene Diimides: Effects of Substituents |
| title_sort | n n bis 2 cyclohexylethyl naphtho 2 3 b 6 7 b dithiophene diimides effects of substituents |
| topic | application of naphthalene diimide organic synthesis supramolecular chemistry organic field-effect transistor crystal structure |
| url | http://www.mdpi.com/1420-3049/21/8/981 |
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