基于四苯基卟啉—二噻吩乙烯光致变色化合物的合成及表征

发布时间：2018-06-25 13:19

本文选题：二芳烯 + 分子开关　；参考：《南京理工大学》2016年硕士论文

【摘要】：二芳基乙烯特别是二噻吩乙烯化合物由于较好的热稳定性和快速响应性在信息存储方面有着潜在的价值。作为有机光存储材料,通常是利用紫外-可见光来检测两个光致变色异构体之间吸收光谱的变化来进行信息读取,被吸收的紫外-可见光部分会不可避免的导致部分光致变色反应的发生,破坏先前写入的数据。为防止检测过程对数据有所损坏,无损读取技术有待研究。四苯基卟啉具有多齿配位作用、特殊的大环共轭芳香体系以及具有强烈的荧光性,通过对四苯基卟啉的修饰从而将二芳基乙烯单元通过化学键或配位键连接到荧光基团卟啉上,本论文主要研究内容如下：(1)以2-甲基噻吩为原料,经过氯代,二酮加成及自缩合成环反应制得1,2-二(2-甲基-5-氯-3-噻吩基)-环戊烯,再通过与吡啶盐酸盐偶联生成单吡啶基二噻吩乙烯和对称吡啶基二噻吩乙烯,通过MS、1H NMR验证了每步产物的结构,并用UV-Vis光谱探讨了两种光致变色分子的光致变色性能。(2)设计一种新的对称吡啶基二噻吩乙烯的合成路线,以2-甲基噻吩为原料,经过Suzuki偶联、傅克酰基化、McMurry环合3步反应制备1,2-二(2-甲基-5-吡啶基-3-噻吩基)环戊烯,总收率61%。利用紫外-可见吸收光谱、荧光光谱对该化合物及其与不同金属离子相互作用的光致变色性能以及应用进行了研究。(3)以吡咯及苯甲醛为原料,以水杨酸为质子化剂,以二甲苯为溶剂,并加入DMSO作为除水剂合成了四苯基卟啉,其结构经MS及1H NMR进行表征,再将四苯基卟啉与金属进行配位生成金属四苯基卟啉。(4)金属四苯基卟啉与吡啶基二噻吩乙烯进行络合反应,研究了不同溶剂对合成产率的影响,测试其光学性能。
[Abstract]:Diarylethylene, especially dithiophene, has potential value in information storage due to its good thermal stability and rapid response. As an organic light storage material, UV-visible light is usually used to detect changes in absorption spectra between two photochromic isomers for information reading. The absorption of ultraviolet-visible light will inevitably lead to partial photochromic reactions, destroying previously written data. In order to prevent the detection process from damaging the data, the nondestructive reading technology needs to be studied. Tetraphenylporphyrin has polydentate coordination, special macrocyclic conjugated aromatic system and strong fluorescence. By modifying tetraphenylporphyrin, the diaryl ethylene unit is connected to the fluorescent group porphyrin by chemical bond or coordination bond. The main contents of this thesis are as follows: (1) 1) 1 (2-methyl-5-chloro-3-thiophenyl) -cyclopentene was synthesized from 2-methylthiophene by chlorinated, diketone addition and self-condensation cyclization. After coupling with pyridine hydrochloride to produce monopyridyl dithiophene and symmetrical pyridyl dithiophene, the structure of each product was confirmed by MS ~ 1H NMR. The photochromic properties of two photochromic molecules were studied by UV-Vis spectroscopy. (2) A new synthesis route of symmetrical pyridyl dithiophene was designed, and 2-methylthiophene was coupled with Suzuki. In the 3-step reaction of McMurry cyclization with Fourier acyl group, 1mg-2-bis (2-methyl-5-pyridyl -3-thiophenyl) cyclopentene was prepared in total yield of 61g 路mol ~ (-1) 路L ~ (-1) 路L ~ (-1). The photochromic properties and applications of the compound and its interaction with different metal ions were studied by UV-Vis absorption and fluorescence spectra. (3) Pyrrole and benzaldehyde were used as raw materials and salicylic acid as protonation agent. Tetraphenylporphyrin was synthesized with xylene as solvent and DMSO as water remover. Its structure was characterized by MS and 1H NMR. Then tetraphenylporphyrin was coordinated with metal to form metal tetraphenylporphyrin. (4) Metallic tetraphenylporphyrin was complexed with pyridyl dithiophene. The effects of different solvents on the yield were studied and their optical properties were tested.
【学位授予单位】：南京理工大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O626

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