Synthesis And Investigation Of Perylene Derivative With Novel Structure

In this article, the development of application in photoelectric material of Donor-Acceptor organic molecular is investigated and presented. Moreover, through reading and researching plenty of literatures about photoelectric material, there are three bottleneck which seriously restrict the development of photoelectric material: (1) for most organic photoelectric material, the absorption of solar light spectra is limited. Due to the absorption of solar light is deficiently, other energy transformed from solar energy by organic photoelectric material are finite; (2) the process of transformation from optical energy to electric energy always accompanies electronic excitation, transmission and acceptance. And that the behavior of electron induces oxidation and reduction of compounds, which easily lead to the changes of organic compounds structure and performance resulting in low transformation efficiency. (3) due to low regularity of the structure of most organic compounds, the electron which transports in organic compounds is very easy to be scattered and trapped, causing low electron mobility.Perylene-3,4,9,10-tetracarboxylic acid bisimides (PBIs) represent a class of highly thermostable n-type semiconductors with relatively high electron affinity and excellent transport property. They have been proven to be good building blocks for constructing supramolecules and giant-molecular systems. Therefore, more and more attention has been being focused on the modification of perylene bisimide structures through synthetic routes to improve their chemical and physical properties, which is achieved by two strategies: the modification at the imide nitrogen or at the bay position of the perylene core. By nucleophilic substitution, 1,6,7,12-tetrabromoperyle- ne-3,4,9,10-tetracarboxylic acid bisanhydride which is obtained by reaction between perylene-3,4,9,10-tetracarboxylic acid bisanhydride and bromine, reacts with 2-ethylhexylamine, leading to N,N′-Di(2-ethylhexyl)-1,6,7,12-tetrabromoperylene-3,4, 9,10-tetracarboxylic acid bisimide which has a good solubility in the general organic solvents. Subsequently, through Stille coupling, a novelπ-conjugated polymer with structure close to planar is synthesized by link at the bay position of N,N′-Di(2-ethylh- exyl)-1,6,7,12-tetrabromoperylene-3,4,9,10-tetracarboxylic acid bisimide. The structu- re of the polymer is confirmed by FI-IR and NMR, and its optical properties are researched by UV-vis and Normalized emission spectra.In Stille coupling, the influence of number-average molecular weight of the compound by different reaction time and dosage of palladium catalyst is also investigaed. Through a series of experiments, when the reaction time is 72 hours and dosage of palladium catalyst is 52μmol, the largest number-average molecular weight is achieved. The low degree of polymerization for this kind of polymer is probably due to the highly tensile force caused by the geometric structure of such polymers close to plane.Due to plenty of perylene cores in target product, it is beneficial to packing between moleculars, which results in easily transport of electron. Moreover, because of the existence ofπ-conjugated structure, the gain and loss of a spot of electron has very little influence to the structure and properties of the compound. The analysis about UV-vis spectra of the polymer shows that the major absorption wavelength is 300nm-750nm which matches the wavelength of solar light. These data show that the polymer has a potential ability as n-type organic semiconductor material.Through three synthetic methods, three perylene imide linked siloxane are synthesized. Compared the three methods, it is best that propionic acid as solvent, and the synthetic method is discussed. The research of properties of the product represent that the product has good structure, thermal property and optical property.