Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant

Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant

The atropisomeric dopant 2,2‘,6,6‘-tetramethyl-3,3‘-dinitro-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (1) induces a ferroelectric SmC* phase when doped into the SmC liquid crystal hosts 2-(4-butyloxyphenyl)-5-octyloxypyrimidine (PhP1) and (±)-4-[(4-methylhexyl)oxy]phenyl 4-decyloxybenzoate (PhB). The...

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Veröffentlicht in:Journal of the American Chemical Society 2002-11, Vol.124 (45), p.13513-13518
Hauptverfasser: Hartley, C. Scott, Lazar, Carmen, Wand, Michael D, Lemieux, Robert P
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Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Liquid crystals
Orientational order of liquid crystals
electric and magnetic field effects on order
Physics
Structure of solids and liquids
crystallography
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container_end_page 13518
container_issue 45
container_start_page 13513
container_title Journal of the American Chemical Society
container_volume 124
creator Hartley, C. Scott
Lazar, Carmen
Wand, Michael D
Lemieux, Robert P
description The atropisomeric dopant 2,2‘,6,6‘-tetramethyl-3,3‘-dinitro-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (1) induces a ferroelectric SmC* phase when doped into the SmC liquid crystal hosts 2-(4-butyloxyphenyl)-5-octyloxypyrimidine (PhP1) and (±)-4-[(4-methylhexyl)oxy]phenyl 4-decyloxybenzoate (PhB). The propensity of dopant 1 to induce a spontaneous polarization (polarization power) is much higher in PhP1 than in PhB (1555 nC/cm2 vs
doi_str_mv 10.1021/ja026458d
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Scott ; Lazar, Carmen ; Wand, Michael D ; Lemieux, Robert P</creator><creatorcontrib>Hartley, C. Scott ; Lazar, Carmen ; Wand, Michael D ; Lemieux, Robert P</creatorcontrib><description>The atropisomeric dopant 2,2‘,6,6‘-tetramethyl-3,3‘-dinitro-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (1) induces a ferroelectric SmC* phase when doped into the SmC liquid crystal hosts 2-(4-butyloxyphenyl)-5-octyloxypyrimidine (PhP1) and (±)-4-[(4-methylhexyl)oxy]phenyl 4-decyloxybenzoate (PhB). The propensity of dopant 1 to induce a spontaneous polarization (polarization power) is much higher in PhP1 than in PhB (1555 nC/cm2 vs &lt;35 nC/cm2), which is attributed to a greater propensity of 1 to undergo chirality transfer via core−core interactions with PhP1. In previous work, we postulated that a chiral perturbation exerted by 1 in PhP1 amplifies the polarization power of the dopant by causing a chiral distortion of the mean field potential (binding site) constraining the dopant in the SmC host, as described by the Chirality Transfer Feedback (CTF) model. To test the validity of the CTF model, and to provide a more direct assessment of the chiral perturbation exerted by dopant 1 on surrounding host molecules, we measured the effect of 1 on the polarization power of other chiral dopants acting as probes. In one series of experiments, (S,S)-5-(2,3-difluorooctyl)-2-(4-octylphenyl)pyridine (MDW950) and (S)-4-(1-methylheptyloxy)phenyl 4-decyloxybenzoate (4), which mimic the structures of PhP1 and PhB, were used as probes. In another series of experiments, the atropisomeric dopant 2,2‘,3,3‘,6,6‘-hexamethyl-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (2) was used as probe in PhP1. The results of the probe experiments suggest that dopant 1 exerts a much stronger chiral perturbation in PhP1 than in PhB. 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Scott</creatorcontrib><creatorcontrib>Lazar, Carmen</creatorcontrib><creatorcontrib>Wand, Michael D</creatorcontrib><creatorcontrib>Lemieux, Robert P</creatorcontrib><title>Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The atropisomeric dopant 2,2‘,6,6‘-tetramethyl-3,3‘-dinitro-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (1) induces a ferroelectric SmC* phase when doped into the SmC liquid crystal hosts 2-(4-butyloxyphenyl)-5-octyloxypyrimidine (PhP1) and (±)-4-[(4-methylhexyl)oxy]phenyl 4-decyloxybenzoate (PhB). The propensity of dopant 1 to induce a spontaneous polarization (polarization power) is much higher in PhP1 than in PhB (1555 nC/cm2 vs &lt;35 nC/cm2), which is attributed to a greater propensity of 1 to undergo chirality transfer via core−core interactions with PhP1. In previous work, we postulated that a chiral perturbation exerted by 1 in PhP1 amplifies the polarization power of the dopant by causing a chiral distortion of the mean field potential (binding site) constraining the dopant in the SmC host, as described by the Chirality Transfer Feedback (CTF) model. To test the validity of the CTF model, and to provide a more direct assessment of the chiral perturbation exerted by dopant 1 on surrounding host molecules, we measured the effect of 1 on the polarization power of other chiral dopants acting as probes. In one series of experiments, (S,S)-5-(2,3-difluorooctyl)-2-(4-octylphenyl)pyridine (MDW950) and (S)-4-(1-methylheptyloxy)phenyl 4-decyloxybenzoate (4), which mimic the structures of PhP1 and PhB, were used as probes. In another series of experiments, the atropisomeric dopant 2,2‘,3,3‘,6,6‘-hexamethyl-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (2) was used as probe in PhP1. The results of the probe experiments suggest that dopant 1 exerts a much stronger chiral perturbation in PhP1 than in PhB. More significantly, the results of experiments using 2 as probe show that the chiral perturbation exerted by 1 can amplify the polarization power of another atropisomeric dopant, thus providing the first experimental evidence of the CTF effect.</description><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Liquid crystals</subject><subject>Orientational order of liquid crystals; electric and magnetic field effects on order</subject><subject>Physics</subject><subject>Structure of solids and liquids; crystallography</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNpt0Mtu1DAUBmALUdGhsOAFkDcgsUjxLb4s25RCpSlUMLBgYzmOo3rI2KntSJ23b0YzartgZdn-zq-jH4B3GJ1iRPDntUGEs1p2L8AC1wRVNSb8JVgghEglJKfH4HXO6_nKiMSvwDEmDEuF6gUIF644W3wMMPawufXJDPDGpTKl1uyeM_QBXrqUohtmmLyFS383-Q42aZuLGTK8Ct1kXQfbLTQBnpUUR5_jxu3suR9vXdgO8CKOJpQ34KifR9zbw3kCfl9-WTXfquWPr1fN2bIyVKhSceYsU1xIrHpKqBKKd05KhhEnVAorCFYEs5643jLatUi1xLa96FslOtlSegI-7nPHFO8ml4ve-GzdMJjg4pS1IJzXjKgZftpDm2LOyfV6TH5j0lZjpHfl6sdyZ_v-EDq1G9c9yUObM_hwACZbM_TJBOvzk2MISVmj2VV753Nx94__Jv3TXFBR69XNL339c9Wgv3--62e5xma9jlMKc3f_WfAB7Ryc9g</recordid><startdate>20021113</startdate><enddate>20021113</enddate><creator>Hartley, C. Scott</creator><creator>Lazar, Carmen</creator><creator>Wand, Michael D</creator><creator>Lemieux, Robert P</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20021113</creationdate><title>Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant</title><author>Hartley, C. Scott ; Lazar, Carmen ; Wand, Michael D ; Lemieux, Robert P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-64ec4967819f3239796de8841062387c7219214f2efc43db09b2cbf7fb97d8b33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Liquid crystals</topic><topic>Orientational order of liquid crystals; electric and magnetic field effects on order</topic><topic>Physics</topic><topic>Structure of solids and liquids; crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hartley, C. Scott</creatorcontrib><creatorcontrib>Lazar, Carmen</creatorcontrib><creatorcontrib>Wand, Michael D</creatorcontrib><creatorcontrib>Lemieux, Robert P</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hartley, C. Scott</au><au>Lazar, Carmen</au><au>Wand, Michael D</au><au>Lemieux, Robert P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-11-13</date><risdate>2002</risdate><volume>124</volume><issue>45</issue><spage>13513</spage><epage>13518</epage><pages>13513-13518</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The atropisomeric dopant 2,2‘,6,6‘-tetramethyl-3,3‘-dinitro-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (1) induces a ferroelectric SmC* phase when doped into the SmC liquid crystal hosts 2-(4-butyloxyphenyl)-5-octyloxypyrimidine (PhP1) and (±)-4-[(4-methylhexyl)oxy]phenyl 4-decyloxybenzoate (PhB). The propensity of dopant 1 to induce a spontaneous polarization (polarization power) is much higher in PhP1 than in PhB (1555 nC/cm2 vs &lt;35 nC/cm2), which is attributed to a greater propensity of 1 to undergo chirality transfer via core−core interactions with PhP1. In previous work, we postulated that a chiral perturbation exerted by 1 in PhP1 amplifies the polarization power of the dopant by causing a chiral distortion of the mean field potential (binding site) constraining the dopant in the SmC host, as described by the Chirality Transfer Feedback (CTF) model. To test the validity of the CTF model, and to provide a more direct assessment of the chiral perturbation exerted by dopant 1 on surrounding host molecules, we measured the effect of 1 on the polarization power of other chiral dopants acting as probes. In one series of experiments, (S,S)-5-(2,3-difluorooctyl)-2-(4-octylphenyl)pyridine (MDW950) and (S)-4-(1-methylheptyloxy)phenyl 4-decyloxybenzoate (4), which mimic the structures of PhP1 and PhB, were used as probes. In another series of experiments, the atropisomeric dopant 2,2‘,3,3‘,6,6‘-hexamethyl-4,4‘-bis[(4-nonyloxybenzoyl)oxy]biphenyl (2) was used as probe in PhP1. The results of the probe experiments suggest that dopant 1 exerts a much stronger chiral perturbation in PhP1 than in PhB. More significantly, the results of experiments using 2 as probe show that the chiral perturbation exerted by 1 can amplify the polarization power of another atropisomeric dopant, thus providing the first experimental evidence of the CTF effect.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12418905</pmid><doi>10.1021/ja026458d</doi><tpages>6</tpages></addata></record>
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subjects Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Liquid crystals
Orientational order of liquid crystals
electric and magnetic field effects on order
Physics
Structure of solids and liquids
crystallography
title Detection of Chiral Perturbations in Ferroelectric Liquid Crystals Induced by an Atropisomeric Biphenyl Dopant
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