Supramolecular Self-assembly And Properties Of Bay-substituted Perylene-diimide

The molecular arrangement of organic semiconductors can be efficiently adjust-ed by controlling intermolecular non-covalent interactions,which is essential to or-ganic electronic devices’performance improving.Owing to its directional ability and dynamically reversibility,hydrogen-bond can provide strong self-assembly driving force between molecules to form highly ordered structure.In this dissertation,four perylene bisimide compounds with 3,4,5-tris（dodecyloxy）-1-benzamide as hydro-gen-bonding functional group are synthesized.They are N,N’-bis（3’,4’,5’-tris（dodecyloxy）-1-benzamide）-3,4:9,10-perylene diimide（PDIH）,and its dibromo（PDI-Br）,dicyano（PDI-CN）and diphenyl（PDI-Ph）substituted derivatives.All target compounds have been characterized by nuclear magnetic resonance（NMR）and mass spectrum（MS）.The photophysical,lyotropic self-assembly,thermophysical and electrochemical properties of target compounds have been studied comprehensively.It is much more easier for small bay substituent with small core twist angle to form 1D crosslinked wire self-assembly aggregates,for its strong intermolecular interaction intensity.The intermolecular interaction of target compounds are gradually decreased in the order of PDIH>PDI-CN>PDI-Br>PDI-Ph.All compounds possess good thermal stabability with high decomposition temperatures（T_d）vary from 361℃ to 402℃.The LUMO levels of target compounds are below 4.0 eV,their energy gaps are aroud 2.0 eV,which endue them proper potential as air-stable n-type organic semi-conductors.Whereafter,the OFETs devices of target compounds are fabricated via spin coating with chloroform/THF as solvent.Their performance are optimized by annealing.It shows that,annealing PDIH at 120℃,PDI-Br PDI-CN and PDI-Ph at100℃ for 12 h can achieve their best device performance,whose electron mobilities are about 10^-510^-4 cm²V^-1s^-1,on/off ratio at about 10¹00.