Self-assembly Behavior And Gas Sensing Properties Of Chiral Perylenediimide

Perylene diimide derivatives(PTCDIs)are recognized as good organic dyes and optoelectronic materials in many fields,due to their higher fluorescence quantum ratios,visible light absorption,and good chemical inertness and photostability.The perylene imide derivatives are used as a typical n-type electron-deficient structure,and some of the gas(power supply)such as hydrazine hydrate,ammonia gas and the like can be detected with respect to the semiconductor sensor.In this paper,a series of molecules were synthesized by functionalization of perylene imide,and their self-assembly behavior and sensing properties were studied.The aim of this study is to further study the structure-function relationship of perylene imide derivatives and to promote its application in the field of gas sensors.Abstract The research contents include:1.Three different chiral groups substituted perylene imide derivatives:N,N'-bis(n-hexadecyl)-1,7-bis((S)-1-octyl-3-ol)-3,4,9,10-perylene diimide(SOT),N,N'-bis(n-hexadecyl)-1,7-bis((S)-3-butyl-2-ol)-3,4,9,10-perylenediimide(STB),N,N'-bis(n-dodecyl)-1,7-di((S)-1-phenyl-2-propyn-1-ol)perylene-3,4:9,10-tetracarboxyldiimide(SPP)was prepared and screened with selective response to a variety of substances,measured the higher selectivity and sensitivity of ammonia vapor response.This work mainly focuses on the substitution of three different chiral groups,which have a significant effect on the sensing performance by modulating the reduction potential,the crystalline structure,the ?-? overlap,and the ?-? stacking distance.This topic will analyze in detail the impact of these substituents on the sensing performance.2.Preparation of three perylene imide derivatives substituted with different heteroatoms at the bay: N,N'-bis(S-(+)-3,6-dimethyl-octyl)-3,4,9,10(PDI),N,N'-bis(S-(+)-3,6-dimethyl-octyl)-6,7-thio-3,4,9,10-perylene diimide(PDI-S),N,N'-bis(S-(+)-3,6-dimethyl-octyl)-6,7-selenium-3,4,9,10-perylene diimide(PDI-Se),and selected its selective response to a variety of substances,measured its hydrogen peroxide has a high selectivity and sensitivity.This work mainly focuses on the effect of the substitution of the heteroatoms at the bay level on the twist and self-assembly behavior of the perylene imide conjugated plane.It was found that PDI-S,with its smaller molecular spacing,favors the effect of electron transport to increase the charge transfer rate to compensate for its poor solubility,poor assembly morphology,low LUMO level defects,and thus the best performance.3.The perylene imide derivatives of three different substituents of the bay are prepared: N,N'-bis(S-(+)-3,6-dimethyl-octyl)-3,4,9,10-perylene diimide(PDI),N,N'-bis(S-(+)-3,6-dimethyl-octyl))-1,-nityl-3,4,9,10-perylene diimide(PDIN),N,N'-bis(S-(+)-3,6-dimethyl-octyl))-1,7-dinitro-3,4,9,10-perylene diimide(PDI2N),by detecting the response to gas sensing,found that PDIN has better performance.The study found that although the PDIN reduction level is slightly larger,but its molecular twist angle,molecular spacing and plane slip are the smallest,larger ?-? stacking area,is conducive to electron transport,improve the charge mobility.We would like a detailed analysis of the effects of different substituents,which will help to better understand the structural-performance relationship of organic semiconductors and to facilitate the design and improvement of their device performance.