Synthesis Characterization And Properties Of Novel Water-soluable Zinc Naphthalocyanines

Naphthalocyanine(Nc) is one of the main derivatives of phthalocyanine. With the more extended molecular structure, Naphthalocyanine performs obvious improvements on its oxidation reduction potential, electric conductivity, photoconductivity and catalytic ability but significant reduction in the solubility. This low-solubility of non-substituted Nc in common organic solvents restricted the further research of Nc, making how to improve the solubility being the main subject of the research of Nc. Till now, only sulfonated and phosphate naphthalocyanines have been reported.In this paper, two novel water-soluable Ncs derivates have been designed, synthesized, characterized and studied. The primary results are as follows:1. Two derivates of2,3-dicyanonaphthalene were synthesized:4-((3-bromo-6,7-dicyanonaphthalen-2-yl)methoxy)benzoate and4-((6,7-dicyanonaphthalen-2-yl)methoxy)benzoate. Br4[(4-carboxylate)-phenoxy]4-naphthalocyanine and [(4-carboxylate)-phenoxy]4-naphthalocyanine were directly obtained from the template reaction between the corresponding dinitriles and Znic acetate. They were all characterized by NMR, and the Ncs were also characterized by MALDI-TOF, UV/Vis and IR spectrum. We found that THF-d8is the best NMR solvent for Ncs.2. The aggregation property of Ncs is tested by using UV/Vis spectrum. Nc-1and Nc-s-1show good solubility in common organic solvents such as DMF and THF, and they are soluable in water, comparatively better in the alkalescence. Nc-1shows an obvious aggregation tendency as the ratio of water increases in the water-DMF dual solvent system.3. Photostability is studied by UV/Vis spectrum. With the extension of the illumination time, Nc-2shows obvious decomposition, but Nc-1shows a significant aggregation tendency, which slows the decomposition. Furthermore, Nc-s-1is found that it exists as dimer in the solvent, and the dimer can be separated by light, heat, or ultrasound.4. Optical limiting property of Nc-1and Nc-2is studied. As is shown in the results, when they’re dissolved in DMF ([C]=1×10-2M; cell thickness:2mm), the optical limiting threshold of Nc-1and Nc-s are200and328μJ, respectively.