Synthesis And Photophysical Process Of Perylene Diimide Derivatives

Perylene diimide has excellent optical,thermal and chemical stability,strong and broad absorption in visible region,nearly 100%fluorescence quantum yield,low price,easy modification of chemical structure and excellent photoelectric properties.These advantages make it widely used in several fields of organic solar cells,organic solid-state photovoltaic devices,organic field effect transistors and so on.In this paper,as one of the organic industrial dye,perylene diimide was used as the skeleton,and the substituent ullazine were connected at the bay and ortho positions of perylene diimide to construct D-A perylene diimide derivatives.The structures of these molecules were confirmed by ¹HNMR,¹³CNMR and mass spectrometry,and the photophysical properties of these molecules were studied by femtosecond transient absorption spectroscopy.It mainly includes the following aspects:1.Perylene diimide derivatives with different substitution positions were designed and synthesized by introducing ullazine structural unit into the bay of perylene diimide,and named as B-PDI-1U and F-PDI-1U,respectively.The basic optical characterization and structural identification of these molecules were carried out,and their photophysical processes were explored by means of femtosecond transient spectroscopy.The singlet oxygen production ability of these molecules was analyzed,and the singlet oxygen quantum yields of compounds B-PDI-1U and F-PDI-1U were0.76 and 0.82,respectively,which indicated that these two compounds could be used as type Ⅱ photosensitizers.2.The two-photon absorption properties of perylene diimide derivatives synthesized in this paper were determined by two-photon induced fluorescence method,and the target product F-PDI-1U was confirmed to have two-photon absorption properties.The conjugated product F-PDI-1U has high fluorescence quantum yield and excellent two-photon absorption capacity,and this molecule is expected to show great application prospects in the fields of three-dimensional fluorescence microscopic imaging,optical information storage or photodynamic therapy.3.Perylene diimide derivatives with different substitution positions and numbers were designed by introducing structural units such as ullazine,anthraquinone and benzanthrone into the bay position and ortho position of perylene diimide,and named as O-PDI-1U,O-PDI-3U,O-PDI-4U,B-PDI-AQ,O-PDI-AQ,B-PDI-BZAT,O-PDI-BZAT.These molecules were characterized by optical and structural identification,and their photophysical processes were explored by femtosecond transient spectroscopy.The singlet oxygen was produced by sensitizing oxygen to the compounds with triplet excitons.It was found that the singlet oxygen quantum yields of compounds B-PDI-AQ,O-PDI-AQ,B-PDI-BZAT and O-PDI-BZAT were 0.48,0.58,0.63 and 0.58respectively.