Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules
Tetrafluorocyclohexa-1,3-diene ring-containing tricyclic π-conjugated molecules are promising negative-dielectric-anisotropy guest species for vertical-alignment-type liquid-crystalline (LC) displays. Building on our previous work reporting the excellent photoluminescence (PL) properties of tricycli...
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MDPI AG
2023-08-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/8/1208 |
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| author | Haruka Ohsato Shigeyuki Yamada Motohiro Yasui Tsutomu Konno |
| author_facet | Haruka Ohsato Shigeyuki Yamada Motohiro Yasui Tsutomu Konno |
| author_sort | Haruka Ohsato |
| collection | DOAJ |
| description | Tetrafluorocyclohexa-1,3-diene ring-containing tricyclic π-conjugated molecules are promising negative-dielectric-anisotropy guest species for vertical-alignment-type liquid-crystalline (LC) displays. Building on our previous work reporting the excellent photoluminescence (PL) properties of tricyclic π-conjugated molecules with central tetrafluorocyclohexa-1,3-diene rings, we herein synthesized four analogous molecules with terminal tetrafluorocyclohexa-1,3-diene rings from commercially available precursors and investigated the effects of substituent type and diene ring position on PL and LC properties using microscopic and spectroscopic methods. One of the prepared molecules exhibited a relatively planar molecular structure and formed herringbone-type aggregates via π/F and CH/π interactions instead of forming stacked aggregates via π/π stacking interactions, thus exhibiting relatively strong PL in solution and crystalline states. Moreover, the PL color of this compound depended on the electronic character of its terminal substituents along the long molecular axis. Of the four prepared species, two featured terminal ethyl groups and formed one or more LC phases. The PL properties of these phases indicated that the related phase transition induced changes in the aggregate structure, PL wavelength, and PL color. Our results expand the applicability of CF<sub>2</sub>CF<sub>2</sub> moiety-containing tricyclic compounds as functional molecules for the fabrication of next-generation PL, LC, and PL-LC materials. |
| first_indexed | 2024-03-11T00:01:07Z |
| format | Article |
| id | doaj.art-3660fae43a7c4fc190d7029d233fa1f0 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-11T00:01:07Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-3660fae43a7c4fc190d7029d233fa1f02023-11-19T00:44:54ZengMDPI AGCrystals2073-43522023-08-01138120810.3390/cryst13081208Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated MoleculesHaruka Ohsato0Shigeyuki Yamada1Motohiro Yasui2Tsutomu Konno3Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanFaculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanFaculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanFaculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanTetrafluorocyclohexa-1,3-diene ring-containing tricyclic π-conjugated molecules are promising negative-dielectric-anisotropy guest species for vertical-alignment-type liquid-crystalline (LC) displays. Building on our previous work reporting the excellent photoluminescence (PL) properties of tricyclic π-conjugated molecules with central tetrafluorocyclohexa-1,3-diene rings, we herein synthesized four analogous molecules with terminal tetrafluorocyclohexa-1,3-diene rings from commercially available precursors and investigated the effects of substituent type and diene ring position on PL and LC properties using microscopic and spectroscopic methods. One of the prepared molecules exhibited a relatively planar molecular structure and formed herringbone-type aggregates via π/F and CH/π interactions instead of forming stacked aggregates via π/π stacking interactions, thus exhibiting relatively strong PL in solution and crystalline states. Moreover, the PL color of this compound depended on the electronic character of its terminal substituents along the long molecular axis. Of the four prepared species, two featured terminal ethyl groups and formed one or more LC phases. The PL properties of these phases indicated that the related phase transition induced changes in the aggregate structure, PL wavelength, and PL color. Our results expand the applicability of CF<sub>2</sub>CF<sub>2</sub> moiety-containing tricyclic compounds as functional molecules for the fabrication of next-generation PL, LC, and PL-LC materials.https://www.mdpi.com/2073-4352/13/8/1208fluorinetetrafluorocyclohexa-1,3-dienephotoluminescenceliquid crystaltricyclic moleculeaggregation |
| spellingShingle | Haruka Ohsato Shigeyuki Yamada Motohiro Yasui Tsutomu Konno Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules Crystals fluorine tetrafluorocyclohexa-1,3-diene photoluminescence liquid crystal tricyclic molecule aggregation |
| title | Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules |
| title_full | Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules |
| title_fullStr | Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules |
| title_full_unstemmed | Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules |
| title_short | Effects of Tetrafluorocyclohexa-1,3-Diene Ring Position on Photoluminescence and Liquid-Crystalline Properties of Tricyclic π-Conjugated Molecules |
| title_sort | effects of tetrafluorocyclohexa 1 3 diene ring position on photoluminescence and liquid crystalline properties of tricyclic π conjugated molecules |
| topic | fluorine tetrafluorocyclohexa-1,3-diene photoluminescence liquid crystal tricyclic molecule aggregation |
| url | https://www.mdpi.com/2073-4352/13/8/1208 |
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