Sythesis And Characterization Of The Cyclic Compound Containing N^C^N Tridentate Ligands And Its Pt(Ⅱ) Complexes

In the field of material science, organic functional molecules with unique molecular structure and excellent photoelectric activity have attracted researcher’s great interests. Organic electroluminescent devices were made of fluorescent material, the internal efficiency can only reach 25%. In principle, the devices internal efficiency can be increased as high as 100% by employing a phosphorescent dye, which greatly improves the photo-luminescent efficiency of the devices. In all kinds of phosphorescent heavy metal complexes, flat square phosphorescent platinum complexes occupies a very important position in the filed of the organic electroluminescent diodes(OLEDs), chemical and biological sensors, cell imaging and molecular self-assembly due to its unique spectral and luminescent properties.The structure of the ligand can greatly affect the light-emitting properties of platinum complexes. Conjugation of the ligand, rigid size, different types of the substituents with electron-donating or electron-withdrawing can affect their luminescence properties. Therefore, this thesis reported the design and synthesize amphiphilic Pt(II) complexes containing N^C^N tridentate ligands cyclic compound units. On the one hand, pyrimidine groups in the skeleton not only can stable platinum(II) complexes LUMO level, but also can reduce the HOMO-LUMO energy gap, so as to obtain the luminescent materials with red-shifted absorption and emission. On the other hand, amphiphilic long chain can improve the solubility of complexes and strengthen their self-assembly capability by using π-π intermolecular forces of the large ring, thereby improving the platinum(II) complexes luminescence properties.The thesis is divided into three parts: Part I: The Synthesis of macrocyclic compound. We designed and synthesized an amphiphilic macrocyclic compound containing two dedecyl chains and two OTEG chains. 3,5-Dibomo-fluorobenzene as a starting material, Compound 5 and Compound 6 were obtained by substitution reaction. Compound 9 and Compound 10 were successfully obtained from 5 by Sonogashira coupling reaction. Compound 7(Boric acid ester monomer intermediate) was obtained from compound 6 by Suzuki-Miyaura coupling reaction. Then, compound 8 was obtained by Suzuki coupling reaction between 7 and 5-bromo-2-iodopyrimidine. Next, the obtained by Sonogashira coupling reaction between the deprotection of compound 10 and 8. Lastly, the macrocycle Compound 1 was successfully obtained from half-ring 11. The optical properties of the macrocyclic compound 1 were studied.Part II: The macrocyclic Pt(II) complex 1a was obtained by the reaction of 1 and K2PtCl4, and the optical properties of 1a were investigated.Part III: Investigating the self-assembly properties of macrocycle compound 1. Spherical structures with different size were observed in the THF-H2 O, while spherical structures with uniform size were obtained in toluene-methanol. The hollow spherical structures were obtained by the self-assembly of 1a in CH2Cl2.