2种烷基取代吖啶酮磺酰氯紫外荧光衍生剂的合成及其光谱性质

Synthesis and spectral quality of two alkylation acridone sulfochlorides ultraluminescence derivatization agents

目的以吖啶酮为原料,合成N-甲基吖啶酮-3-磺酰氯(MASC)和N-乙基吖啶酮-3-磺酰氯(EASC)2种新型紫外荧光衍生剂。方法经N位上烷基化修饰和氯磺化合成MASC和EASC,用紫外、核磁共振、质谱等技术对其进行结构表征,并将MASC、EASC与衍生剂丹磺酰氯(DNS-Cl)的紫外吸收及荧光强度相比较。结果通过紫外、核磁共振、质谱等技术证明了二者即为目标化合物,EASC、MASC与DNS-Cl的摩尔吸光系数之比分别为UVEASC-257 nm/UVDNS-Cl-323 nm=7.57、UVMASC-257 nm/UVDNA-Cl-323 nm=7.75,荧光量子效率之比分别为Φf(EASC)/Φf(DNS-Cl)=4.70、Φf(EASC)/Φf(DNS-Cl)=5.42,与二乙胺衍生的衍生物荧光强度之比分别为If(EASC)/If(DNS-Cl)=97.82、If(MASC)/If(DNS-Cl)=103.38。结论EASC和MASC有较强的紫外吸收与荧光强度,有望用于含氨基类化合物的痕量测定。

Objective To synthesize two novel ultraluminescence derivatization agents which include N-methyl acridone-3-sulfonyl chloride（MASC） and N-ethyl acridone-3-sulfonyl chloride（EASC） taking acridone as raw materials.Methods EASC and MASC were synthesized by the reaction of alkylation on N position and chlorosulfonation with chlorosulfonic acid.The structures of compouds were characterized by UV-Vis,nuclear magnetic resonance（NMR）and mass spectrum（MS）techniques.Then ultraviolet absorption and fluorescence intensity of MASC and EASC were compared with danayl chloride（DNS-Cl）.Results The target compouds were characterized by UV-Vis,NMR and MS techniques.Ratios of molar absorptivity were UVEASC-257 nm/UVDNS-Cl-323 nm=7.57,UVMASC-257 nm/UVDNA-Cl-323 nm=7.75.Ratios of fluorescence quantum yield were Φf（EASC）/Φf（DNS-Cl）=4.70,Φf（EASC）/Φf（DNS-Cl）=5.42;ratios of fluorescence intensity of diethylamine derivatives were If（EASC）/If（DNS-Cl）=97.82,If（MASC）/If（DNS-Cl）=103.38（at the same derivative condition）.Conclusion EASC and MASC have high UV absorptivity and fluourscence intensity,and they can be used to the trace determinate of amine-compouds.