Lateral extension induces columnar mesomorphism in crucifix shaped quinoxalinophenanthrophenazines
Reported here is the columnar mesomorphism of board shaped dyes based on quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (TQPP) derivatives that was induced by an increase in lateral bulk. TQPP derivatives with protons, tert-butyl and 4-tert-butyl-phenyl groups in positions 2 and 11 are compared...
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| المؤلف الرئيسي: | |
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| مؤلفون آخرون: | , , , , , , , |
| التنسيق: | article |
| منشور في: |
2015
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| الوصول للمادة أونلاين: | http://hdl.handle.net/10725/4889 http://dx.doi.org/10.1016/j.tet.2014.11.050 http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php http://www.sciencedirect.com/science/article/pii/S0040402014016226 |
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| الملخص: | Reported here is the columnar mesomorphism of board shaped dyes based on quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (TQPP) derivatives that was induced by an increase in lateral bulk. TQPP derivatives with protons, tert-butyl and 4-tert-butyl-phenyl groups in positions 2 and 11 are compared, as well as dodecylthio, dodecyloxy, phytanylthio, and phytanyloxy side-chains. Only derivatives with 4-tert-butyl-phenyl groups display columnar liquid crystal phases over wide ranges of temperature while all other TQPPs are not liquid crystalline except for the compound with tert-butyl groups and phytanyloxy side-chains that shows a Colr mesophase over a temperature range of 26 °C. The sole attachment of phytanyl groups does not effectively induce columnar mesophases. However, the lateral attachment of bulky groups to the TQPP core induces columnar mesomorphism because of the in-plane aspect ratio decrease and the favored twisted or helical π-stacking of the molecules in columns rather than the parallel co-planar packing. |
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