Preparation And Characterization Of New Luminescent Amide,Sulfonamide And Triarylamine Molecules Bearing 9-Phenoxy-10-phenylanthracene Structure

In recent years,anthracene and its derivatives have received extensive research due to their interesting photophysical,photochemical,and biological properties.Currently,they are research objects in many fields,and their applications in biology,OLEDs,OFETs,polymeric materials,solar cells,and many other organic materials have been studied.Anthracene is a very importantπ-conjugated compound with photoluminescence properties,high fluorescence quantum yield,and excellent optical,electrical,and thermochemical properties.It is widely used in the field of organic luminescent materials.Therefore,starting from anthrone,this article conducts a one-step substitution reaction with 4-fluoronitrobenzene to obtain 9-phenoxy-10-phenylanthracene derivatives,further obtaining diamine monomers,gradually synthesizing 13 anthracene derivatives with fluorescence properties,determining their molecular structures,and testing and analyzing their optical,electrical,and thermal properties.The main contents are as follows:In Chapter 2 of this thesis,using anthrone as the starting material,the monomer 9-（4-nitrophenoxy）-10-（4-nitrobenzene）anthracene was synthesized by an affinity substitution reaction of anthrone with p-fluoronitrobenzene.It was further reduced with palladium carbon to obtain the intermediate 9-（4-aminophenoxy）-10-（4-aminobenzene）anthracene,which was then reacted with acetyl chloride,benzoyl chloride,4-fluorobenzoyl chloride 4-bromobenzoyl chloride and 4-methoxybenzoyl chloride undergo a Friedrich acylation reaction to obtain 9-（4-acetylaminophenoxy）-10-（4-acetylaminophenyl）anthracene（P1）,9-（4-benzamidophenoxy）-10-（4-benzamidophenyl）anthracene（P2）,9-[（4-fluorobenzamido）phenoxy]-10-[（4-fluorobenzamido）phenyl] anthracene（P3）,9-[（4-bromobenzamido）phenoxy]-10-[（4-bromobenzamido）phenyl] anthracene（P4）Five luminescent molecules of 9-[（4-methoxybenzamido）phenoxy]-10-[（4-methoxybenzamido）phenyl]anthracene（P5）;The research results show that these five small molecules have stable fluorescence,with the maximum emission wavelength of P2-P5 compounds around 450 nm,belonging to the blue light region,and the maximum emission wavelength of P1 around 500 nm,belonging to the blue green light region.The maximum emission wavelength of the five compounds is minimally affected by the polarity of the solution.The thermal weight loss temperature of 5%of the five compounds is above 350℃,and they have good thermal stability.In Chapter 3 of this thesis,using a synthesis method similar to that in Chapter 2,the intermediate of 9-（4-aminophenoxy）-10-（4-aminobenzene）anthracene was subjected to a Friedelmann acylation reaction with ethanesulfonyl chloride,benzenesulfonyl chloride,p-methylbenzenesulfonyl chloride,and p-cyanobenzenesulfonyl chloride,respectively,to construct four luminescent molecules,specifically:9-（4-methanesulfonamidophenoxy）-10-（4-methanesulfonamidophenyl）anthracene（P6）,9-（4-benzenesulfonamidephenoxy）-10-（4-benzenesulfonamidephenyl）anthracene（P7）,9-[（4-methylbenzenesulfonamide）phenoxy]-10-[（4-methylbenzenesulf onamide）phenyl]anthracene（P8）,9-[（4-cyanobenzenesulfonamide）phenoxy]-10-[（4-cyanobenzenesulfonamide）phenyl]anthracene（P9）.The test results show that the maximum emission wavelengths of the four small molecules are concentrated in the blue region,and the maximum emission wavelength is minimally affected by the polarity of the solution.The four THF containing solutions are significantly inhibited by Fe³⁺and have high sensitivity to different concentrations of Fe³⁺.Except for compound P6,the thermal weight loss temperature of the remaining 3 small molecules of 5%is above 200℃.In Chapter 4 of this thesis,based on the research in the previous two chapters,intermediate weight nitridation of 9-（4-nitroaminophenoxy）-10-（4-aminobenzene）anthracene was followed by reaction with potassium iodide to obtain 9-（4-iodophenoxy）-10-（4-iodobenzene）anthracene intermediates,followed by substitution reactions with diphenylamine,carbazole,phenothiazine,and phenoxazine to synthesize 9-（diphenylamine）phenoxy-10-（diphenylamine）phenylanthracene（P10）,9-（9-carbazolyl）phenoxy-10-（9-carbazolyl）phenylanthracene（P11）,9-（10-phenothiazinyl）phenoxy-10-（10-phenothiazinyl）phenylanthracene（P12）,9-（10-phenothiazinyl）phenoxy-10-（10-phenothiazinyl）phenylanthracene（P13）.The results showed that the maximum emission wavelength of P10 compound was in the blue light region,the maximum emission wavelength of P11 compound was in the yellow light region,the maximum emission wavelength of P12 and P13 compound was in the green light region,and the maximum emission wavelength of P10 and P11 small molecules was slightly affected by the polarity of the solution.P12 and P13 small molecules had a significant red shift in the toluene solution with a small opposite polarity.