Synthesis And Photochromic Properities Of Novel Polyarylnaphthopyran

Organic photochromic materials can read and write information using a total photon mode,they have excellent optical properties and photo-regulation characteristics,so the materials are expected to implement the high-speed storage of information,it is a hot spot of research on chemistry and materials in recent years.Naphthopyran compounds are considered most likely to be the best candidate for information storage,becasued they have good thermal stability and simple structure.At present,such compounds in the application of the existence of fatigue resistance,poor erasability and other issues.Therefore,exploring and modifying the structure of naphthapyrans is one of the tasks we must face.In this paper,two series of polyarylnaphthopyrans were designed and synthesized from（3,4-dimethoxyphenyl）（phenyl）methanone and di-p-tolylmethanone.Naphthopyrans were character rized by ¹H NMR,¹³C NMR,FT-IR and elemental analysis.The photochromic and electrochemical properties of naphthopyrans were studied by UV-vis and cyclic voltammetry.The main work of this dissertation is as follows:1.Five new kinds of 13-butyl-10,11-dimethoxyl-3,3’-diphenyl-3,13-dihydrobenzo[h]indeno[2,1-f]chromen-13-ol derivatives were synthesized through Stobbe condensation,Clasien condensation and Suzuki reaction by using（3,4-dimethoxyphenyl）（phenyl）methanone as starting material.And characterized by FT-IR,¹H NMR,¹³C NMR and elemental analysis methods.2.Six new kinds of 13-butyl-6,11-dimethyl-3,3’-diphenyl-3,13-dihydrobenzo[h]inden[2,1-f]ch romen-13-ol derivatives were synthesisized by using di-p-tolylmethanone as the raw materials.The optimum reaction conditions have been obtained by optimizing experimental condition.And characterized by FT-IR,¹H NMR,¹³C NMR and elemental analysis methods.3.The UV-vis absorption spectra of polarylnaphthopyrans in solution and in PMMA films were investigated respectively,their optical properties include light stability,fading rate and fatigue resistance were studied.The results showed that they had the same good photochromic properties in solution and in film.4.By cyclic voltammetry,The mechanism of photochromism of two series of polyarylnapht hopyrans was explored.The LUMO（-4.34^-2.73）and HOMO（-6.45^-5.65）orbital energy levels were lower according to the test results,indicating that compounds have good electron transport and hole blocking properties.