Design, Synthesis, And Property Of Organic Semiconductors Based On Derivatives Of Perylene Diimides

Organic semiconductors have been paying much attention in the past few years due to their many varieties, low cost and easy to manufacture, developed n-type material with novel structure, high mobility and stability have been the important challenges of this industry. Perylene diimides(PDI) derivatives as a traditional n-type organic semiconductor material receive more and more attention. In this paper, basing on molecule and material design principle, we synthesized a series of derivatives of perylene diimides derivatives, and the target compound was characterized by UV-Vis, fluorescence spectroscopy, electrochemical testing.First,with 3,4,9,10-Perylene tetracarboxylic butyl as starting material, through nitrification, reduction, reaction with butyraldehyde to produce Schiff base, photocyclization with the sunlight, hydrolysis reaction, amination,the PDI derivatives PS-8,12,18 and PS-8',12',18'were synthesized. UV-Vis absorption and Cyclic voltammetry (CV) measurements were performed and the energy levels was calculated. The results indicated that the enlargement along the short axis leaded to a broad absorption not only annelated 3,4,9,10-Perylene tetracarboxylic butyl derivatives but also annelated PDI derivatives. Although their maximum absorption wavelength was blue shift, the absorption range of 3,4,9,10-Perylene tetracarboxylic butyl derivatives was enlarged from 400-500nm to 280-450nm, and the PDI derivatives had a wide absorption at 300-500nm. Electrochemical testing and gaussian calculation show that annelated PDI derivatives maintain the planarity of PDI, and the introduction of N atom reduced the HOMO and LUMO energy level,so they have a stronger ability of accepting electrons.Second, organic two-photon absorption materials have more advantages than inorganic two-photon absorption material, such as low cost,easy for making and integration device ect. Therefore, there is a broad application for this with strong two-photon absorption materials. Basing on the principle of two-photon absorption materials design, molecule FT and PT have been synthesized with ferrocene and pyridine as the electron donor, terephthalonitrile as the electron acceptor, double band asπ-conjugated bridges. The target compound was characterized by high resolution mass spectrometry, nuclear magnetic resonance spectra, UV-Vis, fluorescence spectroscopy. FT has a broad absorption in visible region. It's maximum absorption wavelength is 520 nm. And it's absorbency declines with the increase of the solvent polarity. PT has only one wide absorption band at 300-400nm, it's fluorescence emission is in 397nm.