Synthesis,Properties And Applications Of BN-Fluoranthenes

Fluoranthene is a representative member of the Cyclopenta-Fused Polyaromatic Hydrocarbons(CP-PAHs),which are widely used in the field of organic synthesis and optoelectronic material,and it is also subunit of C60.Modification of the fluoranthene has attracted a lot of attentions.Introduction of heteroatoms precisely into polycyclic aromatic hydrocarbons(PAHs)is one of the effective strategies to tune the properties of PAHs.Replacement of C=C units with an isoelectronic and isosteric B=N units can effectively adjust the photoelectric properties of PAHs without changing the molecular structure.In this thesis,we focused on the development and reactivity of BN-fluoranthene and its derivatives,as well as their application value in the field of optoelectronic materials.In the first part,we designed and synthesized the “parental” BN-fluoranthene 1.Its reactivity towards Br2 is symmetrically investigated.We also studied the regioselectivity by means of theoretical calculations.Afterward,we synthesized the chlorinated BN-fluoranthene 12 a,by introducing chlorine atom in the early stage of synthesis.A series of BN-fluoranthenes were obtained by metal catalyzed crosscoupling reaction of 12 a.The obtained set of X-ray structures elucidated the solid-state structure of these BN-fluoranthenes.The aromaticity of the BN-fluoranthenes was quantified by nuclear independent chemical shift(NICS)calculations.In the second part,we performed photophysical studies,theoretical calculations,and Aggregation-Induced Emission(AIE)characterization on selected BN-fluoranthene and its derivatives(1,12 ah,12ak and 12al).It is shown that the BN-fluoranthenes bearing tri-arylamines have characteristic AIE properties.And these results indicated the BN-aromatic can be utilized in the field of AIE functional luminescent materials.On the other hand,we performed thermogravimetric analysis,theoretical calculations and photophysical studies on four fluoranthene derivatives with different substituents(1,12 a,12aa and 12al),and fabricated UV-OLED light-emitting devices using these four compounds as light-emitting layers.The results show that the introduction of different substituent groups has a large impact on the performance of the OLED devices.Devices based on 1,12 a,12aa emit deep-blue light,while device base on 12 al emit green light.In summary,the thesis focus on the synthesis and derivation of BN-fluoranthene.We also explored the AIE properties and OLED application of selected BN-fluoranthenes.These studies gave insight for the further application of BN-fluoranthenes.