一、以C4-對稱釩酸鹽中心之四聚簇狀體，作為增效式陰離子之篩選及其在向列相液晶中的不對稱放大轉譯作用二、杯[4]芳烴之N-亞柳胺基酸衍生之掌性氧釩錯合物催化α-羥基苯乙酸芐酯進行不對稱氧化反應

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一、以C4-對稱釩酸鹽中心之四聚簇狀體，作為增效式陰離子之篩選及其在向列相液晶中的不對稱放大轉譯作用二、杯[4]芳烴之N-亞柳胺基酸衍生之掌性氧釩錯合物催化α-羥基苯乙酸芐酯進行不對稱氧化反應

Anion Recognition by Asymmetric Amplified Transcription of Vanadyl Quardruplexes in Nematic LC and Application of Calix[4]arene-based Chiral Oxidovanadium(V) Methoxides in Asymmetric Oxidation

羅葳 , Masters　　Advisor：陳建添　　

繁體中文

四聚簇狀體；金屬離子篩選；液晶；手性放大； N-亞柳胺基酸衍生之掌性氧釩錯合物；杯[4]芳烴；不對稱空氣型氧化反

Abstract │ Reference (48) │ Altmetrics

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A tailor-designed vanadyl methoxides bearing p-heptoxyphenyl group at the C5 position of the salicylidene template was synthesized and then subjected to LiVO3 to form loosely bound, Li+-encapsulated quadruplexes. Quadruplexes bearing encapsulated Pb(II) ion, topped with five different anion ligands can be synthesized by dynamic metal-ion specific swapping with different Pb(II) salts. And NO3- ligand could be replaced by other anions due to different binding ability. The chiral tetrameric vanadyl(V) cluster complex allows for efficient halogen anion specific transport. These cluster complexes were utilized as chiral dopants (1 wt%) to nematic LC materials. A systematic survey on the changes of helical pitch was performed and determined by Grandjean method in wedge cells viewed under polarized microscope. It was found that anion with similar geometries, with decreasing in Lewis basicity of the couter anion, the four lower rim regions of the resulting cluster (i.e, the four p-heptoxyphenyl groups) getting farther, thus inducing more helical twisting to the nematic LC phase. This information can be asymmetrically amplified to 0.6-27.5 m pitch change in LC phase. A linear correlation was found between the induced helical pitch (Y-axis) and the electronegativity of halide anion (X-axis) was established.
Besides, we have prepared a new type of calix[4]arene-based chiral oxidovanadium (V) complexes, which was utilized for asymmetric aerobic oxidation and kinetic resolution of benzyl α-hydroxy-phenyl-acetate. The best results of the resolved alcohol we obtained was 75 % ee at 45 % conversion, when the reaction was performed in chlorobenzene 50 ℃.

Reference ( 48 ) 〈TOP〉

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6. Beer, P. D.; Gale, P. A., Angew Chem Int Edit 2001, 40 (3), 486-516.
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7. Sessler, J. L.; Cai, J. J.; Gong, H. Y.; Yang, X. P.; Arambula, J. F.; Hay, B. P., J. Am. Chem. Soc. 2010, 132 (40), 14058-14060.
連結：
23. Eelkema, R.; Feringa, B. L., Org Biomol Chem 2006, 4 (20), 3729-3745.
連結：
24. Finkelmann, H.; Stegemeyer, H., Ber Bunsen Phys Chem 1978, 82 (12), 1302-1308.
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