Modification Of Several Perylene Derivatives And The Nature Of Research

Inspired by intriguing application in molecular electronics, light energy conversion, photocatalysis, and artificial photosynthesis, the photoinduced energy and electron transfer in donor-acceptor systems attract extensive attention. As an important class of functional materials, perylene bisimide derivative possess many advantages of stable structure, oustanding photoelectron properties, high thermal stability and exhibit wide absorption and emission bands in the visible region, which can be widely used in organic solar cell, organic solid state photovoltaic device, organic thin-film field-effect transistor and so on. In this paper, a series of symmetric and asymmetric perylene bisimide derivatives have been designed and synthesized. Three chapters were included in present thesis.The research of synthesis, propertis and applications of these perylene bisimide derivatives have been reviewed in Chapter 1. The asymmetric synthesis of these compounds is the novel innovation.1,7-asymmetrically substituted 3,4:9,10-perylenebis(dicarboximide) dyes (2a, 2b, and 3) with electron donor or acceptor groups have been synthesized in good yields under mild conditions in Chapter 2. The compounds were studied in detail with electrochemistry and steady-state spectroscopy of these perylene bisimides to show the electron effects of the substitutions. The strong electron donating pyrrolidinyl/p- tert-butylphenoxy and electron withdrawing bromine substitutes led to a serious deviation from intrinsic electronic structure of the perylene bisimide core. Futhermore, the packing behaviors both in solid state and in solution were investigated with scanning electron microscopy and absorption spectra respectively. These results were in good agreement with the theory calculations at B3LYP/6-31G* level and made them a valuable addition to the family of robust perylene-based chromophores that can be used to develop new photoactive charge transport materials.We have discussed the direct introduction substituting group on the carbon atom of perylene have been able bring the obvious influence effects for the entire molecular electrochemistry and the photochemistry characteristic, and the introduction of the substitution groups that increases dissolve on the imide nitrogen atom usually not to be able brings too many obvious changes to their absorption and the emmision characteristic. An alternative way to solve the problems is in presented in Chapter 3, we expected direct introduction of electronic substituting groups on the haighly soluble phenoxy-perylene, development the absorption scope of organic functional materials in visible region, causes the UV-vis absorption spectrums of these compounds red shift to near-infrared and the infrared region.