一种用于检测硫化氢的新型异长叶烷基吲唑类颜色比例型探针  

A Novel Isolongifolanylindazole Derivatives Colorimetric Probe for Naked-eye Detection of H_(2)S in Water Environment

作　　者：秦阿慧 巩帅 张燕[2] 高语 王忠龙 王石发[1,2] QIN A-Hui;GONG Shuai;ZHANG Yan;GAO Yu;WANG Zhong-Long;WANG Shi-Fa(Co-Innovation Center of Efficient Processing and Utilization of Forest Resources,Nanjing Forestry University,Nanjing 210037,China;College of Chemical-Engineering,Nanjing Forestry University,Nanjing 210037,China)

机构地区：[1]南京林业大学林业资源高效加工利用协同创新中心,南京210037 [2]南京林业大学化学工程学院,南京210037

出　　处：《分析化学》2021年第11期1845-1854,I0001-I0005,共15页Chinese Journal of Analytical Chemistry

基　　金：国家自然科学基金项目(No.32071707)资助。

摘　　要：以天然长叶烯的衍生物异长叶烷酮为原料,合成了一种异长叶烷基吲唑类颜色比例型探针5,5,9,9-四甲基-3-(4-硝基苯基)-2,4,5,6,7,8,9,9a-八氢-5a,8-桥亚甲基苯并\吲唑(简称BN)。此探针对硫化氢(H_(2)S)具有良好的选择性,在H_(2)S存在时,探针颜色由无色变为黄色,具有响应时间短(24 s)、灵敏度高(检出限为0.31μmol/L)等优点。采用核磁共振(^(1)H NMR)和高分辨质谱(HRMS)等对探针BN与H_(2)S的作用机理进行了研究,结果表明,探针BN分子中的硝基被H_(2)S还原为氨基,同时吡唑环上的氢原子也随之消失。利用密度泛函理论计算验证了探针BN对H_(2)S的光物理性质。此探针可附着在滤纸上,制成检测试纸,并成功应用于环境水样中H_(2)S的检测。Hydrogen sulfide(H_(2)S)plays crucial roles in various physiological process and daily life.However,excess H_(2)S is very harmful to health.Therefore,it is necessary to design a sensitive method for H_(2)S detection.In this work,a novel colorimetric probe 5,5,9,9-tetramethyl-3-(4-nitrophenyl)-2,4,5,6,7,8,9,9a-octahydro-5a,8-methanobenzo\indazole(BN)for naked-eye detection of H_(2)S was developed with longifolene derivative isolongifolenone as the starting material.This probe had great merits including rapid response time(0.4 min),high sensitivity(detection limit of 0.31μmol/L),and high selectivity for H_(2)S detection.The sensing mechanism was confirmed by ^(1)H NMR and HRMS.The experiment results showed that the—NO_(2) group was reduced into—NH 2 group by H_(2)S,and the hydrogen atom on the indazole ring disappeared as soon as probe BN contacted with H_(2)S.The photophysical properties of probe BN toward H_(2)S were examined by density functional theory calculation.Additionally,the probe BN could be loaded on filter paper and was successfully applied to detection of H_(2)S in environmental water samples.

关 键 词：异长叶烷酮 吲唑衍生物 比色型探针 硫化氢 

分 类 号：O657.3[理学—分析化学]