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Synthesis, characterization and self-assembly of new cholesteryl-substitued sym-tetrazine: Fluorescence, gelation and mesogenic properties
Journal of Molecular Liquids ( IF 6 ) Pub Date : 2021-09-17 , DOI: 10.1016/j.molliq.2021.117543
Amerah Alsoliemy 1 , Abdulmajeed F. Alrefaei 2 , Samah J Almehmadi 3 , Samar J. Almehmadi 1 , Aisha Hossan 4 , Mohamed E. Khalifa 5 , Nashwa M. El-Metwaly 1, 6
Affiliation  

Fluorescent liquid crystalline organogels have been considered as proper candidates for low-energy consumption electronic displays particularly for portable flexible electronics. Herein, we synthesized novel fluorescent symmetric 3,6-bis(4-(cholesterylester)phenyl)-1,2,4,5-tetrazine (sym-Tetrazine; DCh-Tz) liquid crystalline low molecular weight organogelator (LMWO). The molecular structure of the prepared sym-Tetrazine was characterized by different spectroscopic methods, including 1H/13C NMR and FT-IR spectra. The new oganogelator, sym-tetrazine, was synthesized via an addition reaction of hydrazine monohydrate with 4-cyanobenzoic acid to give the corresponding dihydrotetrazine. The product of the addition reaction was subjected to an oxidation reaction to give 3,6-bis(4-carboxyphenyl)-tetrazine to interact with cholesterol affording the desired DCh-Tz. It was proved to possess fairly high gelation capability to generate nanofibers in various alcohols, such as 1,6-dihydroxyhexane, n-octanol and n-butanol. The mesogenic phases of the prepared cholesterylester s-tetrazine were studied by POM and DSC. The photophysical properties of the new fluorescent and thermoreversible low molecular weight organogelator from cholesterylester s-tetrazine were discussed. Both of UV-Vis absorption and fluorescence spectra showed a solvatochromic and solvatofluorochromic activities, respectively. The supramolecular self-assembly of the synthesized cholesterylester s-tetrazine occurred via van der Waals and π-stack interaction forces to result in the gelation of various organic solvents. A dried xerogel of the cholesterylester s-tetrazine was studied by scanning electron microscopy (SEM) to show fiber-like nano-scaled scaffolds. Both of cytotoxicity and antimicrobial properties were explored to prove the use the current DCh-Tz for other potential applications, such as bioimaging and drug delivery systems.



中文翻译:

新型胆固醇取代的共四嗪的合成、表征和自组装:荧光、凝胶化和介晶特性

荧光液晶有机凝胶已被认为是低能耗电子显示器的合适候选者,特别是便携式柔性电子设备。在此,我们合成了新型荧光对称 3,6-双(4-(胆固醇酯)苯基)-1,2,4,5-四嗪 ( sym -Tetraazine; DCh-Tz) 液晶低分子量有机凝胶剂 (LMWO)。通过不同的光谱方法,包括1 H/ 13 C NMR 和FT-IR 光谱表征了所制备的sym- Tetraazine的分子结构。新的 oganogelator,sym-四嗪,通过肼一水合物与4-氰基苯甲酸的加成反应合成,得到相应的二氢四嗪。对加成反应的产物进行氧化反应,得到 3,6-双(4-羧基苯基)-四嗪与胆固醇相互作用,得到所需的 DCh-Tz。它被证明具有相当高的凝胶化能力,可以在各种醇中生成纳米纤维,例如 1,6-二羟基己烷、辛醇和丁醇。所制备的cholesterylester介晶相小号-tetrazine由POM和DSC分析。新的荧光和热可逆的低分子量有机胶凝剂的从cholesterylester光物理性质小号-四嗪进行了讨论。UV-Vis 吸收光谱和荧光光谱都分别显示出溶剂化变色和溶剂化氟变色活性。所述超分子自组装的合成cholesterylester的小号-tetrazine经由范德华发生和π -stack相互作用力导致在各种有机溶剂的凝胶化。所述cholesterylester的干燥干凝胶小号-tetrazine通过扫描电子显微镜(SEM),显示纤维状纳米级支架研究。研究了细胞毒性和抗菌特性,以证明当前的 DCh-Tz 可用于其他潜在应用,例如生物成像和药物输送系统。

更新日期:2021-09-20
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