Synthesize And Assembly Of Perylene Bisimide Modified By Melamine Moieties

As a kind of unique n-type organic semiconductor materials, perylene bisimideand its derivatives have a variety of derivative structure which poss unique optical,thermal and photochemical stability. So they are more suitable for the preparation ofphotoelectric functional material and can be applied to a variety of devices. Melamineis easy to be modified chemically. Because of its remarkable properties, which can beused as hydrogen bond donors and receptors Therefore, when the perylene bisimidewas modificeted by chemical method, the conditions for the preparation of the orderlyis low dimensional micro/nano materials structure should be explored, which can bean important basis project on the development of supramolecular chemistry. Four newperylene bisimide containing melamine group were designed and synthesized on thebasis of comprehensive literature. Then the factors of chemical structure, solvent typeand the assembly method were investigated. Findings are as follows：1. Perylene bisimide imide was functioned with2,4-2(laurel amino)-6-(1-aminoadipic amino)-1,3,5-triazine on both ends of a nitrogen atom. The morphologystructure of MPBI-1prepared by the phase transfer and rapid aggregation method,which was charactered by the ultraviolet-visible spectrophotometer and scanningelectron microscope detection methods. When methanol and chloroform was used astwo-phase solvent(volume ratio of1:4), the diameter of about100nm, length ofdozens of micron nanofibers was prepared using phase transfer method can; The samesystem when used fast solvent diffusion method, which is adopted to form a shortfibrous structure. That’s because limited by the self-assembly kinetics, the system wasfar from the aspects of size and regularity of the structure with the phase transfermethod.2. Perylene bisimide imide was functioned by alkyl-phenoxy and adipic aminobridge connect with2,4-2(laurel amino)-6-(1-amino adipic amino)-1,3,5–triazine on the bay-station and the ends of the imide nitrogen atoms.After themolecular structure was changed, the aggregation structure has changed a lot. Whenchloride and methanol was used as two-phase solvent(volume ratio of2:1), the1microns in diameter spheresd can be prepared using phase transfer and fast solventdiffusion, but the former neat degrees are significantly higher than the latter. Whenthe solvent system was changed, the state of aggregation structure can also be altered.As n-hexane and dichloromethane were used as two-phase solvent, the porous network structure can be prepared by using phase transfer method; And law assemble withsharp corners rectangular block structure can be seen with the fast solvent diffusion;After the good solvent changed with chloroform, the system can assemble to themicroporous structure3. When modification on the nitrogen atoms both ends of imide, the functionalmaterials can be got finally. First of all, the morphology structure can be prepared inmethylene chloride/methanol system using phase transfer and fast solvent diffusionmethod, then a shift from fibrous structure to microspheres morphology of processcan be observe; The pore morphology can be got in methylene chloride/n-hexanesystem;The same way,when chloroform was used as the "good" solvent, the systemdid not assemble characteristics of structure after the rapid solvent mixture method.The second, the types of solvents and solvent concentration on the influence ofself-assembly micelle discussed was diacussed. The results show that: in CHCl3solvent, MPBI-3assembles uniform honeycomb structure with diameter of1μmtypical round hole shape. Besides we found that the solvent boiling point andevaporation rate had a greater influence on the morphology structure of honeycombstructure.Finally, Through real-time monitoring imide derivatives MPBI-3growthchanges over time in Methylene chloride/methanol=1/1(vol ol) mixed solvent, Wefound that with the extension of time, the assembly structure integrated microspherestructure into dendritic structure, which evolved into fibrous structure in turn.4. When modification on the nitrogen atoms both ends of imide with the branchedchain groups of2,4-2(laurel amino)-6-(1-amino adipic amino)-1,3,5-triazine, theimpact to the length of alkyl chain imide functional materials can bestudied. The samewith MPBI-3, the compound can also be used in the above two methods of assemblyin methylene chloride and methylene chloride/n-hexane/methanol system formation offibrous and cellular structure respectively, but significantly less than the former inneat degrees. At the same time, MPBI-4in CHCl3solvent can also be assembled fromround hole shape honeycomb structure, the same as the morphology of MPBI-3neat.