The Effect Of Substituents Of Perylenediimide On Supramolecular Self-assembly And Properties

In the n-type organic semiconductor materials, the derivatives of perylene bisimide (PTCDIs)whichhave been got more and more attention. They are widely used in photovoltaic devices, organic field-effecttransistors, gas sensors, fluorescent probes of biological and medical fields. Many research groups havesynthesized Perylene compounds, which not only have neat appearance, but also have stable chemicalproperty. In this paper, by modifying PTCDIs, we have designed and synthesized a series of compoundsand further studied its behavior of self-assembly in solution and other related properties. The main researchwork includes:1. The designed and synthesized three compounds weret (1) N, N’-bis (decyl)-3,4:9,10-perylenediimide (PTCDI-C10),(2) N, N’-bis (decyl alkyl)-1,7-dibromo-3,4:9,10-perylene diimide(PTCDI-Br2C10) and (3) N, N’-bis (decyl)-1,7-two tert-butylphenol3,4:9,10-perylene diimide(PTCDI-BP2C10). And then we researched the self-assembly behavior of these compounds in chloroform/methanol binary mixed solvent, and the performance of micron/nanob-elts devices gas sensers. Theresults suggested that in the hydrazine hydrate (10ppm) atmosphere, PTCDI-BP2C12exhibited its bestsensitive performance, and the performance sensitivity of PTCDI-Br2C10is the worst. It proved that sidechain substituents have a significant effect on the gas sensors of PTCDIs, and this effect was achieved byadjusting the strap and the skeleton structure of the compounds.2.(1) N, N’-bis (1,7-dimethyloctyl)-1,7-dicyanoethyl3,4:9,10-perylene diimide(PTCDI-CNC10),(2) N, N’-bis (1,7-dimethyloctyl)-1,6,7,12-tetrachloro-3,4:9,10-perylene diimide(PTCDI-ClC10) were designed and synthesized. And we have reaserched the different electron withdrawingsubstituents influnced on these compounds self-assembled morphology and performance. Compared withPTCDI-ClC10, it found that PTCDI-CNC10had a lower sensitivity in hydrazine hydrate gas，but higherambient stability in air. It proved that different electron withdrawing substituent had a significant effect onthe gas-sensing sensors, and this effect was less dependent on the morphology and surface area of theassembly, but it was closely related with molecules,structure, energy level and energy band system.3. We have designed and synthesised three compounds,(1) N-octyl-N’-((4- aminophenyl)-β-D-glucoside)-3,4:9,10-perylene diimide (OBAG),(2) N-dodecyl-N’-((4-aminophenyl)-β-D-glucosi-de)-3,4:9,10-perylene diimide (DBAG) and (3) N-hexadecyl-N’-((4-aminophenyl)-β-D-glucos-ide)-3,4:9,10-perylene diimide (HBAG). And we researched that the differentlengths of the alkyl chain substituent have influenced on the circular dichroism spectra of these compoundsand the self-assembled morphology. It found that CD signals of HBAG and OBAG in the THF/H2O mixedsolution have inversed. However, the CD signals of DBAG had no inversion. It proved that alkyl chains ofdifferent lengths substituents had a significant impact on the formation of self-assembled morphology, andit caused by adjusting the interaction of hydrophobic and hydrophilic of the amphiphilic molecules;moreover, it also changed the intermolecular π-π stacking surface, and then lead to the differentconductivity.