The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles
A series of shape-persistent phenylene–ethynylene–naphthylene–butadiynylene macrocycles with different extraannular alkyl groups and intraannular bridges is synthesized by oxidative Glaser-coupling of the appropriate precursors. The intraannular bridges serve in this case as templates that reduce th...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.89 |
| _version_ | 1818462253254443008 |
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| author | Joscha Vollmeyer Ute Baumeister Sigurd Höger |
| author_facet | Joscha Vollmeyer Ute Baumeister Sigurd Höger |
| author_sort | Joscha Vollmeyer |
| collection | DOAJ |
| description | A series of shape-persistent phenylene–ethynylene–naphthylene–butadiynylene macrocycles with different extraannular alkyl groups and intraannular bridges is synthesized by oxidative Glaser-coupling of the appropriate precursors. The intraannular bridges serve in this case as templates that reduce the oligomerization even when the reaction is not performed under pseudo high-dilution conditions. The extraannular as well as the intraannular substituents have a strong influence on the thermal behavior of the compounds. With branched alkyl chains at the periphery, the macrocycles exhibit liquid crystalline (lc) phases when the interior is empty or when the length of the alkyl bridge is just right to cross the ring. With a longer alkyl or an oligoethylene oxide bridge no lc phase is observed, most probably because the mesogene is no longer planar. |
| first_indexed | 2024-12-14T23:59:06Z |
| format | Article |
| id | doaj.art-6bea9bc172aa460c808d4a7f137c18cf |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T23:59:06Z |
| publishDate | 2014-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6bea9bc172aa460c808d4a7f137c18cf2022-12-21T22:43:00ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110191092010.3762/bjoc.10.891860-5397-10-89The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocyclesJoscha Vollmeyer0Ute Baumeister1Sigurd Höger2Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyInstitut für Chemie, Physikalische Chemie, Martin-Luther-Universität Halle-Wittenberg, Von-Danckelmann-Platz 4, 06120 Halle (Saale), GermanyKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyA series of shape-persistent phenylene–ethynylene–naphthylene–butadiynylene macrocycles with different extraannular alkyl groups and intraannular bridges is synthesized by oxidative Glaser-coupling of the appropriate precursors. The intraannular bridges serve in this case as templates that reduce the oligomerization even when the reaction is not performed under pseudo high-dilution conditions. The extraannular as well as the intraannular substituents have a strong influence on the thermal behavior of the compounds. With branched alkyl chains at the periphery, the macrocycles exhibit liquid crystalline (lc) phases when the interior is empty or when the length of the alkyl bridge is just right to cross the ring. With a longer alkyl or an oligoethylene oxide bridge no lc phase is observed, most probably because the mesogene is no longer planar.https://doi.org/10.3762/bjoc.10.89discotic liquid crystalsshape-persistent macrocyclestemplatesX-ray scattering |
| spellingShingle | Joscha Vollmeyer Ute Baumeister Sigurd Höger The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles Beilstein Journal of Organic Chemistry discotic liquid crystals shape-persistent macrocycles templates X-ray scattering |
| title | The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles |
| title_full | The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles |
| title_fullStr | The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles |
| title_full_unstemmed | The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles |
| title_short | The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles |
| title_sort | influence of intraannular templates on the liquid crystallinity of shape persistent macrocycles |
| topic | discotic liquid crystals shape-persistent macrocycles templates X-ray scattering |
| url | https://doi.org/10.3762/bjoc.10.89 |
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