Synthesis And Characterization Of Fulgide Photochromic Compounds Based On Porphyrin And Thiophene Units

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 massive amounts of information, it is a hotspot of research on chemistry and materials in recent years. Heterocyclic fulgide is considered most likely to be developed into information storage materials of photon types, because it has good thermal stability and simple structure. Now these compounds have key issues in the research of application, including low photoquantum yield, poor fatigue resistance and the destruction of record information after read-out, so it is necessary that other groups are introduced to solve these problems.In the paper, thiophene-substituted fulgide has been prepared from with good photochromic properties, then porphyrin unit has been introduced into the fulgide. The contents of this thesis are presented as follows:(1) Thiophene-substituted fulgide has been prepared through Friedel-Crafts acylation, Stobbe condensation and other steps by using 2-methyl thiophene and diethyl succinate as raw materials, the optimum reaction conditions have been obtained by optimizing experimental conditiona, and the structures are characterized by 1H NMR, IR and MS.(2) Optical properties have been studied in the fulgide from (1). The results show that the compound has good photochromic properties, the open and close structure can be converted to each other under certain wavelength of light, which has a good reproducibility; the compound also has good thermal stability and fatigue resistance.(3) Two kinds of amino porphyrin compounds have been synthesized from hemin and TPP, the intermediate NO2TPP has been prepared through two different routes; This part is for the porphyrins into the fugide in preparation.(4) Through imidization reaction, NH2TPP and the fugide have been connected successfully by chemical bond and 5-{2-[1-(5-chloro-2-methyl-3-thienyl) ethylidene]-3-isopropylidene succinimide-N-phenyl}-10,15,30-triphenyl porphyrin has been obtained, photochromic properties of the final product has been studied in comparation with the UV-Vis spectra from (2). The results show that the obvious red shift occurs in the UV-Vis spectra of the compound after modification, the wavelength distance of two absorption bands becomes larger, which is helpful to realize non-destructive readout with the fluorescence property of porphyrin.