The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system

Two types of racemic rodlike Schiff base mesogens with –CN– (type I ) and –NC– (type III ) linkages were prepared. These mesogens possessed either difluoro substitutions at the inner-core position of the phenyl ring or hydroxy group to form intramolecular hydrogen bonding with an ester or/and imin...

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Veröffentlicht in:New journal of chemistry 2019, Vol.43 (4), p.1743-1756
Hauptverfasser: Huang, Chiung-Cheng, Huang, Yu-Chang, Hsieh, Wei-Cheng, Chen, Yen-Jung, Jiang, Shi-Kai, Chen, Bo-Hao, Hsu, I.-Jui, Lee, Jey-Jau
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container_end_page 1756
container_issue 4
container_start_page 1743
container_title New journal of chemistry
container_volume 43
creator Huang, Chiung-Cheng
Huang, Yu-Chang
Hsieh, Wei-Cheng
Chen, Yen-Jung
Jiang, Shi-Kai
Chen, Bo-Hao
Hsu, I.-Jui
Lee, Jey-Jau
description Two types of racemic rodlike Schiff base mesogens with –CN– (type I ) and –NC– (type III ) linkages were prepared. These mesogens possessed either difluoro substitutions at the inner-core position of the phenyl ring or hydroxy group to form intramolecular hydrogen bonding with an ester or/and imine linkage. When the appropriate concentration of chiral additive is doped into them, the incorporation of two fluoro substituents is more useful for blue phase (BP) stabilization than that of a hydroxy group near the ester linkage in Schiff base mesogens. BPI and BPII can be identified by reflectance spectra and polarized optical microscope images. BPII emerges easily on cooling when the appropriate chiral dopant ISO(6OBA)2 or chiral dopant S811 is doped into the Schiff base mesogen having only a hydroxy group near the ester linkage. Interestingly, BPI can be observed when 10–15 wt% ISO(6OBA)2 was doped into the difluoro substituted Schiff base mesogen III during a heating process. The experimental and molecular modeling results indicate that most of the difluorinated Schiff base mesogens with larger dipole moments exhibit wider BP ranges than their corresponding non-fluorinated homologues under the same chirality condition. In addition, wide BPs can be induced for racemic rodlike Schiff base mesogens I in the chiral system and this is easier than that for racemic rodlike Schiff base mesogens III . In Schiff base mesogens I , the dipole moment is dominant for BP stabilization. However, the fluorine substituent effect is the main factor in Schiff base mesogens III .
doi_str_mv 10.1039/C8NJ04493G
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These mesogens possessed either difluoro substitutions at the inner-core position of the phenyl ring or hydroxy group to form intramolecular hydrogen bonding with an ester or/and imine linkage. When the appropriate concentration of chiral additive is doped into them, the incorporation of two fluoro substituents is more useful for blue phase (BP) stabilization than that of a hydroxy group near the ester linkage in Schiff base mesogens. BPI and BPII can be identified by reflectance spectra and polarized optical microscope images. BPII emerges easily on cooling when the appropriate chiral dopant ISO(6OBA)2 or chiral dopant S811 is doped into the Schiff base mesogen having only a hydroxy group near the ester linkage. Interestingly, BPI can be observed when 10–15 wt% ISO(6OBA)2 was doped into the difluoro substituted Schiff base mesogen III during a heating process. The experimental and molecular modeling results indicate that most of the difluorinated Schiff base mesogens with larger dipole moments exhibit wider BP ranges than their corresponding non-fluorinated homologues under the same chirality condition. In addition, wide BPs can be induced for racemic rodlike Schiff base mesogens I in the chiral system and this is easier than that for racemic rodlike Schiff base mesogens III . In Schiff base mesogens I , the dipole moment is dominant for BP stabilization. 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These mesogens possessed either difluoro substitutions at the inner-core position of the phenyl ring or hydroxy group to form intramolecular hydrogen bonding with an ester or/and imine linkage. When the appropriate concentration of chiral additive is doped into them, the incorporation of two fluoro substituents is more useful for blue phase (BP) stabilization than that of a hydroxy group near the ester linkage in Schiff base mesogens. BPI and BPII can be identified by reflectance spectra and polarized optical microscope images. BPII emerges easily on cooling when the appropriate chiral dopant ISO(6OBA)2 or chiral dopant S811 is doped into the Schiff base mesogen having only a hydroxy group near the ester linkage. Interestingly, BPI can be observed when 10–15 wt% ISO(6OBA)2 was doped into the difluoro substituted Schiff base mesogen III during a heating process. 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These mesogens possessed either difluoro substitutions at the inner-core position of the phenyl ring or hydroxy group to form intramolecular hydrogen bonding with an ester or/and imine linkage. When the appropriate concentration of chiral additive is doped into them, the incorporation of two fluoro substituents is more useful for blue phase (BP) stabilization than that of a hydroxy group near the ester linkage in Schiff base mesogens. BPI and BPII can be identified by reflectance spectra and polarized optical microscope images. BPII emerges easily on cooling when the appropriate chiral dopant ISO(6OBA)2 or chiral dopant S811 is doped into the Schiff base mesogen having only a hydroxy group near the ester linkage. Interestingly, BPI can be observed when 10–15 wt% ISO(6OBA)2 was doped into the difluoro substituted Schiff base mesogen III during a heating process. The experimental and molecular modeling results indicate that most of the difluorinated Schiff base mesogens with larger dipole moments exhibit wider BP ranges than their corresponding non-fluorinated homologues under the same chirality condition. In addition, wide BPs can be induced for racemic rodlike Schiff base mesogens I in the chiral system and this is easier than that for racemic rodlike Schiff base mesogens III . In Schiff base mesogens I , the dipole moment is dominant for BP stabilization. However, the fluorine substituent effect is the main factor in Schiff base mesogens III .</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8NJ04493G</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-9533-9642</orcidid><orcidid>https://orcid.org/0000-0001-7187-8900</orcidid></addata></record>
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Chirality
Dipole moments
Dopants
Fluorination
Fluorine
Functional groups
Homology
Hydrogen bonding
Imines
Molecular structure
Protons
Reflectance
Stabilization
title The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system
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