Design, Synthesis And Properties Study Of A New Unsymmetrical Perylene Diimide Derivative

Perylene and its derivatives have very excellent photochemical stability and theirabsorption band is so broad that they can absorb from the visible to the infrared regionlight. Perylene and its derivatives are a kind of high performance photoelectronicfunctional materials. Their self-assembly compound have a wide range of applications,such as organic solar cells, organic electroluminescent devices, organic field-effecttransistors and liquid crystal and other fields. Therefore, design and synthesis of anew-style perylene diimide derivative molecule with high solubility, and investigation intophotoelectric properties of self-assembly aggregation structure have already become a hottopic in the field of scientific community.In this study, we have designed and synthesised two new perylenediimides withdifferent end groups: N, N’-(3,4,5-three-dodecyloxy alkoxy-1-aminophenyl)-3,4,9,10-perylene tetracarboxylic diimide (BIPI) and N-(3,4,5-three-dodecyl-1-amino-phenyl)-N’-(4-amino-pyridine)-3,4,9,10-perylene tetracarboxylic diimide (PDPI) and characterizedtheir molecular structure by FT-IR and1H NMR. For exploring their morphologies, thenwe tested its UV-Vis absorption spectra, polarized light microscopy, X-ray, field emissionscanning electron microscopy.By thermal analysis test we know that PDPI and BIPI have a good thermal stability,and when use polarized light microscope observe them, we can see columnar liquidcrystalline phase texture; By X-ray diffraction, from the Bragg equation we estimate thedistance of adjacent two layers.In this article, we obtained different sizes BIPI and PDPI crystals by solution castingand saturated solution diffusion methods. Then we observed their crystal morphology bypolarizing microscopy, and explored different molecular structures, different solvents,different solution concentrations and different growth patterns on the crystal size andmorphology. The results indicate that the larger concentration, the better the solubility, andthe easier the crystal growth due to the improved accumulation capacity of perylenederivatives; In addition, compared with PDPI, BIPI is easier to get a larger size and more neat crystals.