Synthesis And Properties Of The Functional Silacyclopentadiene Derivatives

Aggregation-caused quenching(ACQ) refers to the normal fluorescent phenomenon that fluorescent substances are emissive strongly in their good solvents but nonemissive in their poor solvents or in aggregated state.This phenomenon is not conducive to the practical application of organic fluorescent substances in solid state or in aggregated state. Therefore, the researchers in order to solve this problem to do a lot of research work. They find a normal fluorescent phenomenon which is aggregation-induced emission(AIE). That is to say, some organic fluorescent molecule are nonemissive or emit weakly in their good solvents but emit strongly in their poor solvents or in aggregated state. In recent few years, organic compounds with AIE effect are a new type of light-emitting materials which have attracted much attention. Silicon miscellaneous cyclopentadiene(silole) derivatives is a typical AIE organic compounds. In this paper, a series of organic compounds containing silole unit have been designed and synthesized. The structure, photophysical properties, thermostabilities, piric acid explosive detection etc. of the new compounds have been investigated. The mainly work are summarized as follows:(1) The new compound is combined a ACQ pyrene with a AIE 1-methyl-2,3,4,5-tetraphenylsilole. Through Karstedt catalytic hydrosilylation reaction, AIE silole derivative containing pyrene unit has been designed and synthesized. The research results on the structure, photophyscial properties and thermostabilities of this compound indicate that the hydrosilylation reaction is a trans-addition reaction; The new fluorescent compound belongs to P-1 space group of triclinic crystal system; The absorption spectrum of the compound solid film is different from that of the solution-state in tetrahydrofuran(THF). But their maximum ultraviolet absorption wavelength are also at 359nm. It begins weightlessness in 265℃. The temperature of Td10 is 370℃. The severe weightlessness phenomenon takes place from 370-495℃. So it has good thermal stability.(2) The new compound is combined a ACQ anthracene with a AIE 1-methyl-2,3,4,5-tetraphenylsilole. Through H2PtCl6·6H2O catalytic hydrosilylation reaction, AIE silole derivative containing anthracene unit has been designed and synthesized. The research results on the structure, photophyscial properties and thermostabilities of this compound indicate that the absorption spectrum of the compound solid film is similar to that of the solution-state in tetrahydrofuran(THF). But their maximum ultraviolet absorption wavelength are different. The maximum ultraviolet absorption wavelength of the solution-state in THF is at 374nm and that of solid film is at 375nm. It begins weightlessness in 265℃. The temperature of Td10 is 370℃. The severe weightlessness phenomenon takes place from 370-495℃. So it has good thermal stability.(3) The new type of chiral compound is synthesiszed through combing an ACQ (R)-(+)-1,1’-binaphthol with an AIE 1-methyl-2,3,4,5-tetraphenylsilole. Through Karstedt catalytic hydrosilylation reaction, AIE silole derivative containing (R)-(+)-1,1’-binaphthol unit has been designed and synthesized. The research results on the structure, photophyscial properties, thermostabilities, piric acid explosive detection and circular dichroism spectrum of this compound indicate that its maxium ultraviolet absorption wavelength are at 340nm. With the increasing of water content, the fluorescent intensity increased. The fluorescence emission wavelength is at 490nm. It has remarkable AIE effect. Under different excitation wavelength, the fluorescent emission spectrum of the new compound is similar to that of 1-methyl-2,3,4,5-tetraphenylsilole. But the fluorescent emission wavelength may, or may not be the same. It begins weightlessness in 265℃. The temperature of Td10 is 370℃. The severe weightlessness phenomenon takes place from 370-495℃. So it has good thermal stability. The new compound keeps the three-dimensional structure of (R)-(+)-1,1’-binaphthol in solution-state and aggregated state so that it has a strong chiral signal. It has good sensitivity to picric acid. The fluorescence quenching can be detected at a picric acid concentration of 1 ppm. It has a chiral in their good solvent or aggregated state.