Synthesis and Mesophase Behavior of Phenylthiophene Based Amphiphilic Molecules
Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri（oxylethylene） moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni（II） and Pd（0） catalyzed coupling reactio...
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| Published in | Chinese journal of chemistry Vol. 30; no. 3; pp. 577 - 584 |
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| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.03.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1001-604X 1614-7065 1614-7065 |
| DOI | 10.1002/cjoc.201280021 |
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| Summary: | Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri（oxylethylene） moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni（II） and Pd（0） catalyzed coupling reaction as key steps. The tri（oxylethylene） moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized op- tical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri（oxylethylene） moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established, |
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| Bibliography: | Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri（oxylethylene） moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni（II） and Pd（0） catalyzed coupling reaction as key steps. The tri（oxylethylene） moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized op- tical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri（oxylethylene） moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established 31-1547/O6 Jing, Shan Zhang, Ruilin Dai, Heng Du, Chao Cheng, Xiaohong Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemistry and Material Engineering, Yunnan University, Kunming, Yunan 650091, China thiophene, amphiphile, C--C coupling reaction, mesophase, oxylethylene the Yunnan Science Foundation - No. 2010CD018 istex:9C252BAF65F8390D133F04782722EB78264D087B ark:/67375/WNG-V5SVBCSD-2 ArticleID:CJOC201280021 the National Natural Science Foundation of China - No. 21074105, 20972133 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
| ISSN: | 1001-604X 1614-7065 1614-7065 |
| DOI: | 10.1002/cjoc.201280021 |