Synthesis And Properties Of Porphyrin Derivatives Modified By Aggregation-Induced Emission Molecules

Porphyrins are known as an excellent near-infrared-emissive fluorescence material.However,the ?-? conjugated coplanar structure of porphyrin derivatives usually produces strong aggregation at high concentration and solid state,causing fluorescence quenching,which greatly limits their application in biological imaging and fluorescence materials and the like.By introducing aggregation-induced emission(AIE)units on the porphyrin skeleton,a novel AIE porphyrin derivative can be obtained by introducing AIE units on the porphyrin skeleton,which is of great significance for the design and synthesis of porphyrin derivatives with strong fluorescence under aggregation and biological application development.In this thesis,a series of simple AIE molecules,such as diphenylacrylonitrile molecules and tetrastyrene molecules,were used as raw materials to synthesize a series of novel porphyrin derivatives with AIE molecules on the porphyrin skeleton through etherification and other reactions.The luminescence properties of porphyrin derivatives and their potential application in cell imaging properties were investigated.The main contents are as follows:In the fisrt chapter,a novel porphyrin derivative with diphenylacrylonitrile unit was designed and synthesized.The results of photophysical properties showed that the introduction of four diphenylacrylonitrile units on the porphyrin skeleton can make the porphyrin emit fluorescence in the solid powder state and there was a fluorescence resonance energy transfer(FRET)effect between the diphenylacrylonitrile unit and the porphyrin core.In addition,the target product had good HeLa cells imaging performance and good biocompatibility by comparison with those traditional porphyrins with aggregation-caused quenching(ACQ).In the second chapter,a novel porphyrin derivative with a tetraphenylene unit on the porphyrin skeleton was obtianed.The novel porphyrin derivative with tetraphenylethylene unit had obvious AIE effect in different water content solutions.And there was also a FRET effect between the tetraphenylethylene unit and the porphyrin nucleus.Meanwhile,the target product exhibited low biotoxicity and good HeLa cells imaging performance.In the following chapter,by introducing diphenylacrylonitrile unit with a long alkoxy chain on the porphyrin skeleton,a novel porphyrin derivative was designed and synthesized.The results suggested that there was still a FRET effect between the diphenylacrylonitrile unit and the porphyrin nucleus by introducing the alkoxy chain into diphenylacrylonitrile.Besides,this target product had an AIE effect as well.In the fourth chapter,by introducing diphenylacrylonitrile unit with an ester group chain on the porphyrin skeleton,a novel porphyrin derivative was designed and synthesized.The investigation of photophysical properties suggested that the introduction of ester-based chains enabled the porphyrin to emit red light in a solid state and the FRET effect between cyano stilbene unit and porphyrin nucleus also can be founded.Moreover,the porphyrin maximum emission wavelength was red-shifted after the introduction of ester-based chains.