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Chiral Polymorphic Hydrazine-based Asymmetric Liquid Crystal Trimers with Resorcinol as Linking Group
Current Organic Synthesis ( IF 1.8 ) Pub Date : 2021-05-31 , DOI: 10.2174/1570179418666210202123935
Yit-Peng Goh 1 , Wan-Sinn Yam 1 , Foo-Win Yip 2 , Gurumurthy Hegde 3
Affiliation  

Introduction: This is the first report on chiral polymorphic hydrazine-based asymmetric liquid crystal trimers, 1-[4'-(4''-(5-Cholesteryloxy)carbonyl)butyloxy]-3-[N-benzylideneoxy-N'-(4'''-decyloxybenzylidene) hydrazine] butyloxybenzenes, and 1-[4'-(4''-(10-cholesteryloxy)carbonyl)nonyloxy]-3-[N-benzylideneoxy-N'-(4'''- decyloxybenzylidene)hydrazine]butyloxybenzenes., in which the hydrazine and cholesterol arms were connected via two flexible methylene spacers (n = 3-12 units and m = 4 or 9, respectively) to the central resorcinol core.

Materials and Methods: FT-IR, 1D and 2D NMR spectroscopy, and CHN microanalysis were used to elucidate the structures of the trimers. Differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction were used to study the transitional and phase properties of the trimers, which were length and spacer parity dependent. Trimers with short spacer length in the cholesteryl arm, m = 4 showed an interesting phase sequence of BP/N*-TGBA*-SmA*.

Results and Discussion: The TGBA* phase was sensitive to spacer length as it was only observed in trimers with short ester linkage. For the long analogues, m = 9, characteristic visible reflection and a much simpler phase sequence with only N* and SmA* phases were observed.

Conclusion: The X-ray diffraction measurements revealed that layer periodicities of the SmA* phase were approximately half the estimated all-trans molecular length (d/L ≈ 0.44-0.52), thus suggesting that the molecules are either strongly intercalated or bent.



中文翻译:

以间苯二酚为连接基团的手性多晶型肼基不对称液晶三聚体

简介:首次报道手性多晶型肼基不对称液晶三聚体,1-[4'-(4''-(5-Cholesteryloxy)carbonyl)丁氧基]-3-[N-benzylideneoxy-N'-( 4'''-癸氧基苯亚甲基)肼]丁氧基苯和1-[4'-(4''-(10-胆固醇氧基)羰基)壬氧基]-3-[N-苯亚甲基氧基-N'-(4'''-癸氧基苯亚甲基) )肼]丁氧基苯。,其中肼和胆固醇臂通过两个柔性亚甲基间隔物(n = 3-12 个单位和 m = 4 或 9,分别)连接到中心间苯二酚核心。

材料和方法:FT-IR、1D 和2D NMR 光谱以及CHN 微量分析用于阐明三聚体的结构。差示扫描量热法、偏光显微镜和 X 射线衍射用于研究三聚体的过渡和相特性,这些特性与长度和间隔子奇偶性有关。胆固醇臂中具有短间隔区长度的三聚体,m = 4,显示出有趣的 BP/N*-TGBA*-SmA* 相序列。

结果与讨论:TGBA* 相对间隔区长度敏感,因为它仅在具有短酯键的三聚体中观察到。对于长类似物,m = 9,观察到特征可见反射和仅具有 N* 和 SmA* 相的更简单的相序。

结论:X 射线衍射测量显示 SmA* 相的层周期性大约是估计的全反式分子长度的一半 (d/L ≈ 0.44-0.52),因此表明分子被强烈嵌入或弯曲。

更新日期:2021-06-08
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