Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings
The studies of crystal structures with hydrogen bonds have been actively pursued because of their moderate stabilization energy for constructing unique structures. In this study, we synthesized a molecular conductor based on 2,6-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene (trans-TTF-py<sub>2<...
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MDPI AG
2020-11-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/12/1081 |
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| author | Shohei Koyama Morio Kawai Shinya Takaishi Masahiro Yamashita Norihisa Hoshino Tomoyuki Akutagawa Manabu Kanno Hiroaki Iguchi |
| author_facet | Shohei Koyama Morio Kawai Shinya Takaishi Masahiro Yamashita Norihisa Hoshino Tomoyuki Akutagawa Manabu Kanno Hiroaki Iguchi |
| author_sort | Shohei Koyama |
| collection | DOAJ |
| description | The studies of crystal structures with hydrogen bonds have been actively pursued because of their moderate stabilization energy for constructing unique structures. In this study, we synthesized a molecular conductor based on 2,6-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene (trans-TTF-py<sub>2</sub>). Two pyridyl groups were introduced into the TTF skeleton toward the structural exploration in TTF-based molecular conductors involved by hydrogen bonds. In the obtained molecular conductor, (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH, short contacts between the pyridyl group and the hydrogen atom of the TTF skeleton were observed, indicating that hydrogen bonding interactions were introduced in the crystal structure. Spectroscopic measurements and conductivity measurement revealed semiconducting behavior derived from π-stacked trans-TTF-py<sub>2</sub> radical in the crystal structure. Finally, these results are discussed with the quantified hydrogen bonding stabilization energy, and the band calculation of the crystal obtained from density functional theory calculation. |
| first_indexed | 2024-03-10T14:33:24Z |
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| id | doaj.art-d30b5770cdd94c77adaf6c4756af7239 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T14:33:24Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
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| series | Crystals |
| spelling | doaj.art-d30b5770cdd94c77adaf6c4756af72392023-11-20T22:27:44ZengMDPI AGCrystals2073-43522020-11-011012108110.3390/cryst10121081Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen BondingsShohei Koyama0Morio Kawai1Shinya Takaishi2Masahiro Yamashita3Norihisa Hoshino4Tomoyuki Akutagawa5Manabu Kanno6Hiroaki Iguchi7Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanInstitute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanInstitute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, JapanThe studies of crystal structures with hydrogen bonds have been actively pursued because of their moderate stabilization energy for constructing unique structures. In this study, we synthesized a molecular conductor based on 2,6-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene (trans-TTF-py<sub>2</sub>). Two pyridyl groups were introduced into the TTF skeleton toward the structural exploration in TTF-based molecular conductors involved by hydrogen bonds. In the obtained molecular conductor, (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH, short contacts between the pyridyl group and the hydrogen atom of the TTF skeleton were observed, indicating that hydrogen bonding interactions were introduced in the crystal structure. Spectroscopic measurements and conductivity measurement revealed semiconducting behavior derived from π-stacked trans-TTF-py<sub>2</sub> radical in the crystal structure. Finally, these results are discussed with the quantified hydrogen bonding stabilization energy, and the band calculation of the crystal obtained from density functional theory calculation.https://www.mdpi.com/2073-4352/10/12/1081tetrathiafulvalenemolecular conductorhydrogen bonding |
| spellingShingle | Shohei Koyama Morio Kawai Shinya Takaishi Masahiro Yamashita Norihisa Hoshino Tomoyuki Akutagawa Manabu Kanno Hiroaki Iguchi Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings Crystals tetrathiafulvalene molecular conductor hydrogen bonding |
| title | Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings |
| title_full | Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings |
| title_fullStr | Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings |
| title_full_unstemmed | Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings |
| title_short | Synthesis, Structure and Physical Properties of (trans-TTF-py<sub>2</sub>)<sub>1.5</sub>(PF<sub>6</sub>)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings |
| title_sort | synthesis structure and physical properties of trans ttf py sub 2 sub sub 1 5 sub pf sub 6 sub ·etoh a molecular conductor with weak ch∙∙∙n hydrogen bondings |
| topic | tetrathiafulvalene molecular conductor hydrogen bonding |
| url | https://www.mdpi.com/2073-4352/10/12/1081 |
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