Design, Synthesis, And Properties Of Rylene Diimides

Due to good photochemical and thermal stabilities, intense photoluminescence, high reduction potential and incredible carrier mobility, perylene-3,4:9,10-tetracarboxylic acid bisimides(PDIs) have extensively studied in organic field-effect transistors, organic solar cells, supramolecular self-assembly, chemical sensors, and a variety of optoelectronic devices. In recent years, the functionalization of PDI and photoelectric properties research is a hot spot in the organic semiconductor materials. Thus, appropriate modification would made PDIs, as promising organic semiconductors with incredible carrier mobility. Through the metal coupling and excessive metal catalytic reaction, we have made the bay and nonbay functionalization of PDIs, and a series of new organic semiconductors functional molecules have been synthesized.The main contents of this dissertation are as follows:Firstly, until now, there are only a few of reports on monobay-functionalization in PDIs, herein, we presented a highly regiospecific synthesis of 4Cldi PDI from tetrachloro-PDI in different amino acid promoted, Cu I-mediated reaction conditions, establishing a synthetic protocol to monobay-functionalized di PDIs. Further, OTFTs devices based on four tetrachlorinated di(perylene diimides)(4Cldi PDI) with different branching point of alkyl chains were carried out systematically studied on the relationship between film microstructure and charge transport. Incorporating a triply linked di PDI core with two-branched N-alkyl substituents results an electron mobility of up to 0.86 cm2V-1s-1.Secondly,Catalyzed by transition metal Ru and Ir, we implemented one step function the nonbay of PDI, and the introduction of boric acid ester, then converted to halogen, can got functionalization reaction intermediates, which will great enrich the synthetic chemistry of PDI. We using single bromine substitution of PDI nonbay compound as a raw material, through Ullmann coupling reaction, synthesized ? ?-PDI2. And its application in organic solar cells was studied.