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 –CN– (type I ) and –NC– (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 |
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container_title | New journal of chemistry |
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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 –CN– (type
I
) and –NC– (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 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2169062033</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2169062033</sourcerecordid><originalsourceid>FETCH-LOGICAL-c259t-be4602da6676c52754c10b210a24a3fb21d405ba0bc4a7f6b9d11ba64004444b3</originalsourceid><addsrcrecordid>eNpFkMtKxDAYhYMoOI5ufIKAO6GaW1O7lEFHZdCF47okaTLTMW1qLovxBXxtU0Zw9R9-vnPgHAAuMbrBiNa3i7vXF8RYTZdHYIYpr4uacHycNWasQCXjp-AshB1CGFccz8DPequhNkarGKAzsHdWq2SFhyH6pGLyGoqhhSYNKnZuEBZuvEvjxAroXWu7Tw3f1bYzBkoRNOx1cBs9QDdAaZOG43b6hihkZ7tvMYXAbsjm7PE5LuxD1P05ODHCBn3xd-fg4_FhvXgqVm_L58X9qlCkrGMhNeOItILziquSVCVTGEmCkSBMUJNVy1ApBZKKicpwWbcYS8EZyqswJukcXB1yR---kg6x2bnkc63QEMxrxAmiNFPXB0p5F4LXphl91wu_bzBqpqGb_6HpL5KlcXo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2169062033</pqid></control><display><type>article</type><title>The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><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</creator><creatorcontrib>Huang, Chiung-Cheng ; Huang, Yu-Chang ; Hsieh, Wei-Cheng ; Chen, Yen-Jung ; Jiang, Shi-Kai ; Chen, Bo-Hao ; Hsu, I.-Jui ; Lee, Jey-Jau</creatorcontrib><description>Two types of racemic rodlike Schiff base mesogens with –CN– (type
I
) and –NC– (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
.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C8NJ04493G</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chirality ; Dipole moments ; Dopants ; Fluorination ; Fluorine ; Functional groups ; Homology ; Hydrogen bonding ; Imines ; Molecular structure ; Protons ; Reflectance ; Stabilization</subject><ispartof>New journal of chemistry, 2019, Vol.43 (4), p.1743-1756</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-be4602da6676c52754c10b210a24a3fb21d405ba0bc4a7f6b9d11ba64004444b3</citedby><cites>FETCH-LOGICAL-c259t-be4602da6676c52754c10b210a24a3fb21d405ba0bc4a7f6b9d11ba64004444b3</cites><orcidid>0000-0002-9533-9642 ; 0000-0001-7187-8900</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Huang, Chiung-Cheng</creatorcontrib><creatorcontrib>Huang, Yu-Chang</creatorcontrib><creatorcontrib>Hsieh, Wei-Cheng</creatorcontrib><creatorcontrib>Chen, Yen-Jung</creatorcontrib><creatorcontrib>Jiang, Shi-Kai</creatorcontrib><creatorcontrib>Chen, Bo-Hao</creatorcontrib><creatorcontrib>Hsu, I.-Jui</creatorcontrib><creatorcontrib>Lee, Jey-Jau</creatorcontrib><title>The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system</title><title>New journal of chemistry</title><description>Two types of racemic rodlike Schiff base mesogens with –CN– (type
I
) and –NC– (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
.</description><subject>Chirality</subject><subject>Dipole moments</subject><subject>Dopants</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Functional groups</subject><subject>Homology</subject><subject>Hydrogen bonding</subject><subject>Imines</subject><subject>Molecular structure</subject><subject>Protons</subject><subject>Reflectance</subject><subject>Stabilization</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFkMtKxDAYhYMoOI5ufIKAO6GaW1O7lEFHZdCF47okaTLTMW1qLovxBXxtU0Zw9R9-vnPgHAAuMbrBiNa3i7vXF8RYTZdHYIYpr4uacHycNWasQCXjp-AshB1CGFccz8DPequhNkarGKAzsHdWq2SFhyH6pGLyGoqhhSYNKnZuEBZuvEvjxAroXWu7Tw3f1bYzBkoRNOx1cBs9QDdAaZOG43b6hihkZ7tvMYXAbsjm7PE5LuxD1P05ODHCBn3xd-fg4_FhvXgqVm_L58X9qlCkrGMhNeOItILziquSVCVTGEmCkSBMUJNVy1ApBZKKicpwWbcYS8EZyqswJukcXB1yR---kg6x2bnkc63QEMxrxAmiNFPXB0p5F4LXphl91wu_bzBqpqGb_6HpL5KlcXo</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Huang, Chiung-Cheng</creator><creator>Huang, Yu-Chang</creator><creator>Hsieh, Wei-Cheng</creator><creator>Chen, Yen-Jung</creator><creator>Jiang, Shi-Kai</creator><creator>Chen, Bo-Hao</creator><creator>Hsu, I.-Jui</creator><creator>Lee, Jey-Jau</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0002-9533-9642</orcidid><orcidid>https://orcid.org/0000-0001-7187-8900</orcidid></search><sort><creationdate>2019</creationdate><title>The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system</title><author>Huang, Chiung-Cheng ; Huang, Yu-Chang ; Hsieh, Wei-Cheng ; Chen, Yen-Jung ; Jiang, Shi-Kai ; Chen, Bo-Hao ; Hsu, I.-Jui ; Lee, Jey-Jau</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-be4602da6676c52754c10b210a24a3fb21d405ba0bc4a7f6b9d11ba64004444b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chirality</topic><topic>Dipole moments</topic><topic>Dopants</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Functional groups</topic><topic>Homology</topic><topic>Hydrogen bonding</topic><topic>Imines</topic><topic>Molecular structure</topic><topic>Protons</topic><topic>Reflectance</topic><topic>Stabilization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Chiung-Cheng</creatorcontrib><creatorcontrib>Huang, Yu-Chang</creatorcontrib><creatorcontrib>Hsieh, Wei-Cheng</creatorcontrib><creatorcontrib>Chen, Yen-Jung</creatorcontrib><creatorcontrib>Jiang, Shi-Kai</creatorcontrib><creatorcontrib>Chen, Bo-Hao</creatorcontrib><creatorcontrib>Hsu, I.-Jui</creatorcontrib><creatorcontrib>Lee, Jey-Jau</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Chiung-Cheng</au><au>Huang, Yu-Chang</au><au>Hsieh, Wei-Cheng</au><au>Chen, Yen-Jung</au><au>Jiang, Shi-Kai</au><au>Chen, Bo-Hao</au><au>Hsu, I.-Jui</au><au>Lee, Jey-Jau</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effects of molecular structure and functional group of a rodlike Schiff base mesogen on blue phase stabilization in a chiral system</atitle><jtitle>New journal of chemistry</jtitle><date>2019</date><risdate>2019</risdate><volume>43</volume><issue>4</issue><spage>1743</spage><epage>1756</epage><pages>1743-1756</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Two types of racemic rodlike Schiff base mesogens with –CN– (type
I
) and –NC– (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
.</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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language | eng |
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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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