Several Studies, Synthesis And Properties Of Functional Organic Compounds Based On Perylene

Perylene dyes have found widespread applications ranging from industrial pigments to components of molecular photonic devices. As an important class of functional materials, perylene bisimide derivatives 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 derivatives which have excellent photoelectronic properties have been designed and synthesized. Four chapters were included in this article, and the main contents of each chapter will be described in the followings.The research of synthesis, propertis and applications of these perylene bisimide derivatives together with the synthesis of perylene monoimide derivatives have been reviewed in Chapter 1. The applications of the perylene derivatives, especially used as the materials of solar cells were emphasized. The thesis aims to design and synthesize a series of novel perylene detivatives with excellent photoelectronic properties.A series of perylene monoimide derivatives have been synthesized in Chapter 2. An efficient method has been develeped to synthesize perylene monoimide from commercially available perylene dianhydride. Three kinds of perylene monoimides have been synthesized in this chapter.Bromination of perylene bisimide dyes have been developed from the commercially available perylene dianhydride. Novel perylene bisimides were obtained by substitution of the bromine atoms with electron donor or acceptor groups in good yields under mild conditions in Chapter 3. The absorption spectra indicate that their absorption bands undergo a significant bathochromic shift along with band broadening with the increase of the aromatic systems.A novel substitution reaction of perylene bisimides has been developed in Chapter 4. A series of Ph2PO group substituted perylene bisimides have been synthesized firstly by reaction of lithium diphenylphosphide with corresponding PBI dyes. The substituted group is attached to the PBI core atα-position instead of usual substitution of halogen atom at bay-area. Owing to the shield or deshield effect of the Ph2PO group, the adjacent proton on perylene core and the tertiary proton at a nearer cyclohexyl group shift significantly in 1H-NMR spectra. The substitution results in a slight red-shift both in absorption and emission spectra and keeps the high fluorescence of the PBI dyes. This reaction develops a new method to modify PBI dyes.