Combination of an Aromatic Core and Aromatic Side Chains Which Constitutes Discotic Liquid Crystal and Organogel Supramolecular Assemblies
This paper reports unique and unusual formations of columnar liquid crystals and organogels by self-assembling discotic molecules, which are composed of an aromatic hexaazatriphenylene (HAT) core and six flexible aromatic side chains. In HAT derivatives 3a, with 4‘-(N,N-diphenylamino)biphenyl-4-yl c...
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Veröffentlicht in: | Langmuir 2005-02, Vol.21 (4), p.1261-1268 |
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creator | Ishi-i, Tsutomu Hirayama, Tomoyuki Murakami, Ko-ichi Tashiro, Hiroshi Thiemann, Thies Kubo, Kanji Mori, Akira Yamasaki, Sumio Akao, Tetsuyuki Tsuboyama, Akira Mukaide, Taihei Ueno, Kazunori Mataka, Shuntaro |
description | This paper reports unique and unusual formations of columnar liquid crystals and organogels by self-assembling discotic molecules, which are composed of an aromatic hexaazatriphenylene (HAT) core and six flexible aromatic side chains. In HAT derivatives 3a, with 4‘-(N,N-diphenylamino)biphenyl-4-yl chains, 3b, with 4‘-[N-(2-naphthyl)-N-phenylamino]biphenyl-4-yl chains, and 3c, with 4‘-phenoxybiphenyl-4-yl chains, the two-dimensional hexagonal packings can be created by their self-assembling in the liquid crystalline phase, which were characterized by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction analysis. In certain solvents, HAT molecules 3a−c can form the viscoelastic fluid organogels, in which one-dimensional aggregates composed of the HAT molecules are self-assembled and entangled into three-dimensional network structures. The organogel structures were analyzed by scanning electron microscopy observation, 1H NMR, UV−vis, and circular dichroism spectroscopy. In contrast to 3a−c, none of the liquid crystalline and organogel phases could be formed from 3d and 3e with short aromatic side chains including a phenylene spacer, and 3f (except a few specific solutions) and 3g without terminal diarylamino and phenoxy groups. In 3a−c, the aromatic side chains with terminal flexible groups make up soft regions that cooperatively stabilize the liquid crystalline and organogel supramolecular structures together with the hard regions of the hexaazatriphenylene core. |
doi_str_mv | 10.1021/la047874+ |
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In HAT derivatives 3a, with 4‘-(N,N-diphenylamino)biphenyl-4-yl chains, 3b, with 4‘-[N-(2-naphthyl)-N-phenylamino]biphenyl-4-yl chains, and 3c, with 4‘-phenoxybiphenyl-4-yl chains, the two-dimensional hexagonal packings can be created by their self-assembling in the liquid crystalline phase, which were characterized by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction analysis. In certain solvents, HAT molecules 3a−c can form the viscoelastic fluid organogels, in which one-dimensional aggregates composed of the HAT molecules are self-assembled and entangled into three-dimensional network structures. The organogel structures were analyzed by scanning electron microscopy observation, 1H NMR, UV−vis, and circular dichroism spectroscopy. In contrast to 3a−c, none of the liquid crystalline and organogel phases could be formed from 3d and 3e with short aromatic side chains including a phenylene spacer, and 3f (except a few specific solutions) and 3g without terminal diarylamino and phenoxy groups. In 3a−c, the aromatic side chains with terminal flexible groups make up soft regions that cooperatively stabilize the liquid crystalline and organogel supramolecular structures together with the hard regions of the hexaazatriphenylene core.</description><identifier>ISSN: 0743-7463</identifier><identifier>EISSN: 1520-5827</identifier><identifier>DOI: 10.1021/la047874+</identifier><identifier>PMID: 15697269</identifier><identifier>CODEN: LANGD5</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; General and physical chemistry</subject><ispartof>Langmuir, 2005-02, Vol.21 (4), p.1261-1268</ispartof><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a444t-4692737ed1fcf08281c61a3beeadece027dd897eeaef0f9531e633b5a87c83963</citedby><cites>FETCH-LOGICAL-a444t-4692737ed1fcf08281c61a3beeadece027dd897eeaef0f9531e633b5a87c83963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/la047874+$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/la047874+$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16527672$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15697269$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ishi-i, Tsutomu</creatorcontrib><creatorcontrib>Hirayama, Tomoyuki</creatorcontrib><creatorcontrib>Murakami, Ko-ichi</creatorcontrib><creatorcontrib>Tashiro, Hiroshi</creatorcontrib><creatorcontrib>Thiemann, Thies</creatorcontrib><creatorcontrib>Kubo, Kanji</creatorcontrib><creatorcontrib>Mori, Akira</creatorcontrib><creatorcontrib>Yamasaki, Sumio</creatorcontrib><creatorcontrib>Akao, Tetsuyuki</creatorcontrib><creatorcontrib>Tsuboyama, Akira</creatorcontrib><creatorcontrib>Mukaide, Taihei</creatorcontrib><creatorcontrib>Ueno, Kazunori</creatorcontrib><creatorcontrib>Mataka, Shuntaro</creatorcontrib><title>Combination of an Aromatic Core and Aromatic Side Chains Which Constitutes Discotic Liquid Crystal and Organogel Supramolecular Assemblies</title><title>Langmuir</title><addtitle>Langmuir</addtitle><description>This paper reports unique and unusual formations of columnar liquid crystals and organogels by self-assembling discotic molecules, which are composed of an aromatic hexaazatriphenylene (HAT) core and six flexible aromatic side chains. In HAT derivatives 3a, with 4‘-(N,N-diphenylamino)biphenyl-4-yl chains, 3b, with 4‘-[N-(2-naphthyl)-N-phenylamino]biphenyl-4-yl chains, and 3c, with 4‘-phenoxybiphenyl-4-yl chains, the two-dimensional hexagonal packings can be created by their self-assembling in the liquid crystalline phase, which were characterized by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction analysis. In certain solvents, HAT molecules 3a−c can form the viscoelastic fluid organogels, in which one-dimensional aggregates composed of the HAT molecules are self-assembled and entangled into three-dimensional network structures. The organogel structures were analyzed by scanning electron microscopy observation, 1H NMR, UV−vis, and circular dichroism spectroscopy. In contrast to 3a−c, none of the liquid crystalline and organogel phases could be formed from 3d and 3e with short aromatic side chains including a phenylene spacer, and 3f (except a few specific solutions) and 3g without terminal diarylamino and phenoxy groups. In 3a−c, the aromatic side chains with terminal flexible groups make up soft regions that cooperatively stabilize the liquid crystalline and organogel supramolecular structures together with the hard regions of the hexaazatriphenylene core.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><issn>0743-7463</issn><issn>1520-5827</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpl0MuO0zAUBmALgZhSWPACyAtASCjgW-xkWcJVVJqROoDExnKck6kHJ-7YicS8Ak-NSwtdsLLO8adfRz9Cjyl5RQmjr70hQlVKvLyDFrRkpCgrpu6iBVGCF0pIfoYepHRNCKm5qO-jM1rKWjFZL9CvJgytG83kwohDj82IVzEMeba4CRHyojttNq4D3GyNGxP-tnV2m82YJjfNEyT81iUb9mztbmbX4Sbepsn4PxHn8cqM4Qo83sy7aIbgwc7eRLxKCYbWO0gP0b3e-ASPju8SfXn_7rL5WKzPP3xqVuvCCCGmQsiaKa6go73tScUqaiU1vAUwHVggTHVdVas8Qk_6uuQUJOdtaSplK15LvkTPD7m7GG5mSJMe8uHgvRkhzElLJSiVuaolenGANoaUIvR6F91g4q2mRO-L13-Lz_TJMXNuB-hO8Fh0Bs-OwCRrfB_NaF06OVkyJRXLrjg4lyb4-e_fxB_5Lq5KfXmx0euLz5s3X78zvc99evDGJn0d5jjm6v6_7zeeDqdh</recordid><startdate>20050215</startdate><enddate>20050215</enddate><creator>Ishi-i, Tsutomu</creator><creator>Hirayama, Tomoyuki</creator><creator>Murakami, Ko-ichi</creator><creator>Tashiro, Hiroshi</creator><creator>Thiemann, Thies</creator><creator>Kubo, Kanji</creator><creator>Mori, Akira</creator><creator>Yamasaki, Sumio</creator><creator>Akao, Tetsuyuki</creator><creator>Tsuboyama, Akira</creator><creator>Mukaide, Taihei</creator><creator>Ueno, Kazunori</creator><creator>Mataka, Shuntaro</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>20050215</creationdate><title>Combination of an Aromatic Core and Aromatic Side Chains Which Constitutes Discotic Liquid Crystal and Organogel Supramolecular Assemblies</title><author>Ishi-i, Tsutomu ; Hirayama, Tomoyuki ; Murakami, Ko-ichi ; Tashiro, Hiroshi ; Thiemann, Thies ; Kubo, Kanji ; Mori, Akira ; Yamasaki, Sumio ; Akao, Tetsuyuki ; Tsuboyama, Akira ; Mukaide, Taihei ; Ueno, Kazunori ; Mataka, Shuntaro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a444t-4692737ed1fcf08281c61a3beeadece027dd897eeaef0f9531e633b5a87c83963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ishi-i, Tsutomu</creatorcontrib><creatorcontrib>Hirayama, Tomoyuki</creatorcontrib><creatorcontrib>Murakami, Ko-ichi</creatorcontrib><creatorcontrib>Tashiro, Hiroshi</creatorcontrib><creatorcontrib>Thiemann, Thies</creatorcontrib><creatorcontrib>Kubo, Kanji</creatorcontrib><creatorcontrib>Mori, Akira</creatorcontrib><creatorcontrib>Yamasaki, Sumio</creatorcontrib><creatorcontrib>Akao, Tetsuyuki</creatorcontrib><creatorcontrib>Tsuboyama, Akira</creatorcontrib><creatorcontrib>Mukaide, Taihei</creatorcontrib><creatorcontrib>Ueno, Kazunori</creatorcontrib><creatorcontrib>Mataka, Shuntaro</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Langmuir</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ishi-i, Tsutomu</au><au>Hirayama, Tomoyuki</au><au>Murakami, Ko-ichi</au><au>Tashiro, Hiroshi</au><au>Thiemann, Thies</au><au>Kubo, Kanji</au><au>Mori, Akira</au><au>Yamasaki, Sumio</au><au>Akao, Tetsuyuki</au><au>Tsuboyama, Akira</au><au>Mukaide, Taihei</au><au>Ueno, Kazunori</au><au>Mataka, Shuntaro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Combination of an Aromatic Core and Aromatic Side Chains Which Constitutes Discotic Liquid Crystal and Organogel Supramolecular Assemblies</atitle><jtitle>Langmuir</jtitle><addtitle>Langmuir</addtitle><date>2005-02-15</date><risdate>2005</risdate><volume>21</volume><issue>4</issue><spage>1261</spage><epage>1268</epage><pages>1261-1268</pages><issn>0743-7463</issn><eissn>1520-5827</eissn><coden>LANGD5</coden><abstract>This paper reports unique and unusual formations of columnar liquid crystals and organogels by self-assembling discotic molecules, which are composed of an aromatic hexaazatriphenylene (HAT) core and six flexible aromatic side chains. In HAT derivatives 3a, with 4‘-(N,N-diphenylamino)biphenyl-4-yl chains, 3b, with 4‘-[N-(2-naphthyl)-N-phenylamino]biphenyl-4-yl chains, and 3c, with 4‘-phenoxybiphenyl-4-yl chains, the two-dimensional hexagonal packings can be created by their self-assembling in the liquid crystalline phase, which were characterized by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction analysis. In certain solvents, HAT molecules 3a−c can form the viscoelastic fluid organogels, in which one-dimensional aggregates composed of the HAT molecules are self-assembled and entangled into three-dimensional network structures. The organogel structures were analyzed by scanning electron microscopy observation, 1H NMR, UV−vis, and circular dichroism spectroscopy. In contrast to 3a−c, none of the liquid crystalline and organogel phases could be formed from 3d and 3e with short aromatic side chains including a phenylene spacer, and 3f (except a few specific solutions) and 3g without terminal diarylamino and phenoxy groups. In 3a−c, the aromatic side chains with terminal flexible groups make up soft regions that cooperatively stabilize the liquid crystalline and organogel supramolecular structures together with the hard regions of the hexaazatriphenylene core.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15697269</pmid><doi>10.1021/la047874+</doi><tpages>8</tpages></addata></record> |
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title | Combination of an Aromatic Core and Aromatic Side Chains Which Constitutes Discotic Liquid Crystal and Organogel Supramolecular Assemblies |
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