树枝状Silole化合物的合成及光电性能研究
摘要
本论文设计并合成了一个含silole与苯乙炔构成共轭的树枝状低聚物1,3,5-三siloles基苯,在合成目标物树枝的过程中共采用三种合成路线。首先采用三乙炔基苯与氯代不对称silole化合物反应以期制得树枝结构,由于目标树枝产物的产率低,中间体活性低等原因,此路线不适合作为树枝的合成路线；第二条路线利用三溴苯为原料,制得单个三异丙基硅保护的三乙炔基苯与溴代不对称silole反应,该路线由于在脱保护基时破坏了底物,因此也不适合作为树枝的合成路线；第三种合成路线采用三甲基氯化硅保护三乙炔基苯的单个炔基,再与不对称溴代silole反应制得树枝化合物,脱去保护基后与三碘苯反应得到目标产物1,3,5-三siloles基苯。
对目标化合物及副产物进行结构表征(1H NMR,13C NMR, EI或ESI),并对各化合物进行光电性能测试,其中包括紫外-可见吸收光谱、荧光光谱的测试,进一步研究发现目标化合物存在聚集诱导发光增强(AIEE)效应,当溶剂中不良溶剂水的比例增加到70%及以上时,化合物的荧光强度明显增强。
该类树枝状Silole低聚物对PA、TNT等多硝基易爆物,具有荧光淬灭检测效应,对PA和TNT的Stern-Volmer荧光淬灭常数分别为8762 M-1和5704 M-J,检测限达到1ppm。
A dendrimers polymer named 1,3,5-trisilolesbenzene was designed and synthesized, it included Silole dendrons and phenylacetylene. For the dendron we have designed three synthetic routes. Firstly, we designed the reaction between triethynylbenzene and 1,1-dimethyl-3,4-diphenyl-2-Cl-5-phenylethynylsilole, the first route is not proper because of the low yield of the target and the low activity. Secondly, we designed the reaction between 1-triisopropylsilylethynyl-3,5-ethynylbenzene and 1,1-dimethyl-3,4-diphenyl-2-Br-5-phenyl-ethynylsilole. The second route is not proper because of the substrate is destroyed when deprotection. Thirdly, we desigined the protective group was trimethylchlorosilane, after deprotection, the latter reacted with triiodo-benzene to obtain the target dendrimer 1,3, 5-trisiloles-benzene.
The compounds were confirmed by1H NMR,13C NMR, El or ESI. Their optoelectronic property, such as UV-vis, Fluorescent, were also studied. These compounds have good AIEE effect, when water was added up to 70%, the fluorescent become stronger.
Their fluorescent were quenched in present of PA or TNT, the Stern-Volmer constant for PA and TNT was 8762 M-1and 5704 M-1 respectively, and the limit of detection is lppm. It means that they can be used as sensor to detected nitroaromatic explosives.
对目标化合物及副产物进行结构表征(1H NMR,13C NMR, EI或ESI),并对各化合物进行光电性能测试,其中包括紫外-可见吸收光谱、荧光光谱的测试,进一步研究发现目标化合物存在聚集诱导发光增强(AIEE)效应,当溶剂中不良溶剂水的比例增加到70%及以上时,化合物的荧光强度明显增强。
该类树枝状Silole低聚物对PA、TNT等多硝基易爆物,具有荧光淬灭检测效应,对PA和TNT的Stern-Volmer荧光淬灭常数分别为8762 M-1和5704 M-J,检测限达到1ppm。
A dendrimers polymer named 1,3,5-trisilolesbenzene was designed and synthesized, it included Silole dendrons and phenylacetylene. For the dendron we have designed three synthetic routes. Firstly, we designed the reaction between triethynylbenzene and 1,1-dimethyl-3,4-diphenyl-2-Cl-5-phenylethynylsilole, the first route is not proper because of the low yield of the target and the low activity. Secondly, we designed the reaction between 1-triisopropylsilylethynyl-3,5-ethynylbenzene and 1,1-dimethyl-3,4-diphenyl-2-Br-5-phenyl-ethynylsilole. The second route is not proper because of the substrate is destroyed when deprotection. Thirdly, we desigined the protective group was trimethylchlorosilane, after deprotection, the latter reacted with triiodo-benzene to obtain the target dendrimer 1,3, 5-trisiloles-benzene.
The compounds were confirmed by1H NMR,13C NMR, El or ESI. Their optoelectronic property, such as UV-vis, Fluorescent, were also studied. These compounds have good AIEE effect, when water was added up to 70%, the fluorescent become stronger.
Their fluorescent were quenched in present of PA or TNT, the Stern-Volmer constant for PA and TNT was 8762 M-1and 5704 M-1 respectively, and the limit of detection is lppm. It means that they can be used as sensor to detected nitroaromatic explosives.
引文
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