通过点击法合成新型杯[4]芳烃-荧光素偶联物及其光催化活性固体脂质纳米粒子的制备。
New Calix[4]arene-Fluoresceine Conjugate by Click Approach-Synthesis and Preparation of Photocatalytically Active Solid Lipid Nanoparticles.
机构信息
Organic and Medical Chemistry Department, Kazan Federal University, 18 Kremlevskaya St., 420008 Kazan, Russia.
Alexander E. Arbuzov Institute of Organic & Physical Chemistry, 8 Arbuzov Str., 420088 Kazan, Russia.
出版信息
Molecules. 2022 Apr 9;27(8):2436. doi: 10.3390/molecules27082436.
New fluorescent systems for photocatalysis, sensors, labeling, etc., are in great demand. Amphiphilic ones are of special interest since they can form functional colloidal systems that can be used in aqueous solutions. A new macrocycle platform for click chemistry and its adduct with o-propargylfluoresceine was synthesized and characterized using modern physical techniques. Nanosized solid lipid nanoparticles (SLNs) from the calixarene-fluoresceine adduct were synthesized through the solvent injection technique and well-characterized in the solution and in solid state using light-scattering and microscopy methods. The maximum fluorescence intensity of the SLNs was found to be in the pH range from 7 to 10. The Förster resonance energy transfer (FRET) efficiency from SLNs to rhodamine 6g was found to be 97.8%. Finally, pure SLNs and the FRET system SLNs-Rh6G were tested in model photocatalytic ipso oxidative hydroxylation of phenylboronic acid under blue LED light. The SLNs-Rh6G system was found to be the best, giving an almost qualitative phenol yield, which was shown by HPLC-UV analysis.
新的荧光体系在光催化、传感器、标记等方面有很大的需求。两亲性荧光体系特别有趣，因为它们可以形成功能性胶体体系，可用于水溶液中。本文采用现代物理技术合成了一种新的点击化学大环平台及其与邻炔丙基荧光素的加合物，并对其进行了表征。通过溶剂注入技术，从杯芳烃-荧光素加合物中合成了纳米级固体脂质纳米粒（SLN），并通过光散射和显微镜方法在溶液和固态中对其进行了很好的表征。发现 SLN 的最大荧光强度在 pH 值为 7 到 10 之间。发现从 SLN 到罗丹明 6G 的Förster 共振能量转移（FRET）效率为 97.8%。最后，在蓝色 LED 光下，在模型光催化邻位氧化羟基化苯硼酸的反应中，对纯 SLN 和 FRET 体系 SLNs-Rh6G 进行了测试。结果表明，SLNs-Rh6G 体系的性能最佳，HPLC-UV 分析表明几乎得到了定性的苯酚产率。
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