Synthesis And Property Of Fluorescent Carbazole And Phenothiazine Derivatives Based On 1,3,5-Tribenzoylbenzene

The Aggregation-induced emission(AIE)phenomenon has applied in organic light-emitting materials rapidly since the view of AIE effect presented by Tang's group in 2001.The features of AIE molecules which switch to high-efficiency luminescence emition in state of aggregation has overcome the shortcomings of traditional luminophores aggregation-caused quenching(ACQ).This anomaly overcome the shortcomings of conventional luminophores aggregation-caused quenching(ACQ)effect.The molecule featuring AIE character break the limitations of conventional luminophores in application(organic light-emitting element must be doped in application,the concentration of molecules applied in fluorescence detection can not be high,etc.),so it applied in the field of organic light emitting materials has vast development prospects.Phenothiazine and carbazole has been widely applied in optical materials because they have a good hole transport ability.Carbazole molecules exhibit a planar structure and phenothiazine are non-planar structure on the spatial configuration and both of them are electron-rich group,so it plays an important role in the design and synthesis of optical materials.In this dissertation,1,3,5-tribenzoylbenzene acting as matrix fraction was first introduced into the AIE phenomenon,carbazole and phenothiazine were substituent groups.Based on these concepts we successfully design and synthesize two types of organic fluorescent molecules with D-?-A and D-A structure,the electron donor(D)is carbazolyl or phenothiazinyl,electron acceptor(A)is carbonyl group and fluorine atom in the structure.The AIE and other properties were studied and results shows:1.The carbazolyl modified compound MCDFBB and DCMFBB having aggregation-induced emission enhancement(AIEE)characters and compounds MCDFBB,DCMFBB and TCBB have solid fluorescence,its colors are green-yellow,palegreen and cyan.2.Among the three substituted phenothiazinyl modified compounds DPMFBB,TPBB having AIE character and also have solid fluorescence,its colors are orange-yellow and orange.3.The emission spectra of the molecules featuring AIE and AIEE characters have redshift with tetrahydrofuran/water mixed solvent polarity changes with different fractions of water demonstrated the presence of intramolecular charge transfer effect(ICT).That may caused by the restriction of intramolecular rotations and twisted intramolecular change transfer effects.HOMO and LUMO orbital distribution by computation chemistry could demonstrated it.4.TGA shows MCDFBB,DCMFBB,TCBB,MPDFBB,DPMFBB and TPBB have high thermal decomposition temperature and computational chemistry indicate that the compounds have a very small energy gap between first singlet excited state and the first excited triplet state could be explained that they have delayed fluorescence properties and having a potential application as light emitting photovoltaic element non-doped emitting layer materials with AIE and delayed fluorescence characters.