芳香双炔醇的合成及其对硝基苯的荧光猝灭研究  

Synthesis of aromatic double alkynol and the fluorescence quenching effect of nitrobenzene

作　　者：刘健[1,2] 吴红波[3] 赵杰[1,2] 王新颖[1,2] 

机构地区：[1]安徽理工大学能源与安全学院,安徽淮南232001 [2]安徽理工大学煤矿安全高效开采省部共建教育部重点实验室,安徽淮南232001 [3]安徽理工大学化工学院,安徽淮南232001

出　　处：《安全与环境学报》2013年第4期161-163,共3页Journal of Safety and Environment

基　　金：国家自然科学基金项目(51004003);安徽省教育厅自然科学基金重点项目(KJ2010A091)

摘　　要：以9,10-二溴蒽和2-甲基-3-丁炔-2-醇为原料,通过Sonogashira钯催化偶联反应,合成9,10-二(2-甲基-3-丁炔-2-醇)蒽,并对其紫外和荧光性能进行了研究。通过试验和高斯理论研究了该化合物对硝基苯的荧光响应。结果表明,该物质表现出较高的荧光量子效应,荧光量子产率达到55%。该化合物与硝基苯之间存在能量传输,使该物质发生荧光猝灭,有望用于微痕量爆炸物的检测。This paper takes as its targets the exploration of the compound＇s ultraviolet and the fluorescent properties in the tetrahydrofuran solution and the fluorescence response of nitrobenzene effect to the resultant through experiments and study of Gaussian theory.As a result of our study,we have successfully synthesized aromatic double alkynol,9,10-bis（2-methyl-3-butyne-2-alcohol） anthracene by way of Sonogashira Reaction with the raw materials of 9,10-dibromoanthracene and 2-acetylene-2-methyl-3-butyl alcohol,with the relative high yield of the reaction,whose structure is characterized by FTIR and HNMR.The results of our experiments show that the characteristic UV absorption peaks of the compound were found located in 383 nm,407 nm,429 nm whereas its fluorescence emission peaks were situated in 439 nm,464 nm,493 nm.Thus,the results prove high fluorescence quantum yield to 55% with the diphenyl anthracene taken as a standard reference parameter.This also serves as a prerequisite for the compound used as fluorescence material in the analysis test.The compound is also found having a gradually fluorescent quenching effect when nitrobenzene is added to its tetrahydrofuran solution,which was ascribed to energy transfer between the slackened electronic nitrobenzene and the rich electronic resultant,particularly,when the electron-donating hydroxyl group introduced as the terminal group of the resultant can help to enhance the energy transfer between the compound and the nitro compounds.The calculation based on Gaussian theory reveals that the HOMO energy level of nitrobenzene is-7.75 eV while the LUMO energy level is-2.91 eV,which are lower than those of the HOMO energy level（-4.99 eV） and LUMO energy level（-1.97 eV） of 9,10-bis（2-methyl-3-butyne-2-alcohol） anthracene.In the dimer of nitrobenzene and the compound,the electronics of excited state in the resultant helps to cross the threshold of the LUMO energy level of nitrobenzene,and then go back to the ground state of the compound from LUMO energy level

关 键 词：有机化学 芳香双炔醇 光谱 硝基化合物 荧光猝灭 

分 类 号：TJ55[兵器科学与技术—军事化学与烟火技术]