酮类甲醛荧光探针的合成及其光学性质
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摘要
设计合成了两种化合物4-氨基4-(4-甲氧基苯基)-3-丁烯-2-酮(1b)和4-氨基-4-(1,3-亚甲二氧基苯基-5-基)-3-丁烯-2-酮(2b),测试了其在不同甲醛含量下的紫外吸收光谱及单光子荧光光谱。当含有100μmol/L和5μmol/L的甲醛时,化合物1b和2b的紫外吸收峰强度分别达到其最大值。在单光子荧光方面,化合物1b的荧光发射峰位置在384 nm,与紫外吸收峰相比红移50 nm。化合物2b的荧光发射峰呈现出双峰形状,其发射峰位置分别在384 nm及411 nm左右。当加入15μmol/L的甲醛时,化合物2b的411 nm处的荧光发射峰明显增强,两峰的重叠程度降低,可作为检测甲醛的特征变化。以上数据表明,化合物1b和2b不仅能够对微量甲醛产生响应,也可作为一种理想平台为更进一步拓宽化合物1b和2b在监测生物体系中甲醛荧光生物成像上的应用奠定理论基础。
Two new vinylmethylketone derivative,4-amino-4-(4-methoxyphenyl) but-3-en-2-one(1 b) and 4-amino-4-(1,3-benzodioxol-5-yl) but-3-en-2-one(2 b) were synthesized and investigated as a possible fluorescent probe for formaldehyde detection. The linear absorption and fluorescent spectra of 1 b and 2 b in different formaldehyde concentration were investigated. The results indicate that the compound 1 b and 2 b have a intricate variation trend existing in UV-Vis absorption spectra and one-photon fluorescence spectra,respectively. In terms of single photon fluorescence,the fluorescence emission peak of compound 1 b is located at 384 nm,which is 50 nm red shift compared with UV absorption peak. The fluorescence emission peak of compound 2 b consists of two peaks located at 384 nm and 411 nm,respectively. When 15 μmol/L of formaldehyde is added,the fluorescence emission peak of the compound 2 b is obviously enhanced and the overlap degree of the twopeak is reduced,which can be used to detect the characteristics of formaldehyde. These results show that 4-amino-4-(4-methoxyphenyl) but-3-en-2-one(1 b) and 4-amino-4-(1,3-benzodioxol-5-yl) but-3-en-2-one(2 b) are able to be as a promising candidate for formaldehyde detection.
Two new vinylmethylketone derivative,4-amino-4-(4-methoxyphenyl) but-3-en-2-one(1 b) and 4-amino-4-(1,3-benzodioxol-5-yl) but-3-en-2-one(2 b) were synthesized and investigated as a possible fluorescent probe for formaldehyde detection. The linear absorption and fluorescent spectra of 1 b and 2 b in different formaldehyde concentration were investigated. The results indicate that the compound 1 b and 2 b have a intricate variation trend existing in UV-Vis absorption spectra and one-photon fluorescence spectra,respectively. In terms of single photon fluorescence,the fluorescence emission peak of compound 1 b is located at 384 nm,which is 50 nm red shift compared with UV absorption peak. The fluorescence emission peak of compound 2 b consists of two peaks located at 384 nm and 411 nm,respectively. When 15 μmol/L of formaldehyde is added,the fluorescence emission peak of the compound 2 b is obviously enhanced and the overlap degree of the twopeak is reduced,which can be used to detect the characteristics of formaldehyde. These results show that 4-amino-4-(4-methoxyphenyl) but-3-en-2-one(1 b) and 4-amino-4-(1,3-benzodioxol-5-yl) but-3-en-2-one(2 b) are able to be as a promising candidate for formaldehyde detection.
引文
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[3]袁帅,刘峥,赖丽燕,等.3种对苯二甲醛类巯基席夫碱分子荧光光谱的量子化学研究[J].发光学报,2013,34(5):585-589.YUAN S,LIU Z,LAI L Y,et al..Quantum chemical study on the fluorescence spectroscopy of three kinds of 1,4-phthalaldehyde schiff base molecule[J].Chin.J.Lumin.,2013,34(5):585-589.(in Chinese)
[4]周娴,董山山,董双石,等.基于Er3+∶YAl O3/Ti O2的可见光催化降解室内甲醛[J].发光学报,2015,36(7):769-774.ZHOU X,DONG S S,DONG S S,et al..Photocatalytic degradation of indoor formaldehyde by Er3+∶YAl O3/Ti O2photocatalyst under visible light irradiation[J].Chin.J.Lumin.,2015,36(7):769-774.(in Chinese)
[5]宋月,高春英,乔琳,等.顺序注射化学发光分析法测定空气中的甲醛[J].发光学报,2009,30(4):467-472.SONG Y,GAO C Y,QIAO L,et al..A sequential injection method coupled with chemiluminescence detection for the determination of formaldehyde in air[J].Chin.J.Lumin.,2009,30(4):467-472.(in Chinese)
[6]MAJUMDER P K,KUMAR V L.Inhibitory effects of formaldehyde on there-productive system of male rats[J].Indian J.Physiol.Pharmacol.,1995,39(1):80-82.
[7]SALTHAMMER T,MENTESE S,MARUTZKY R.Formaldehyde in the indoor environment[J].Chem.Rev.,2010,110(4):2536.
[8]UNZETA M,SOL M,BOADA M,et al..Semicarbazide-sensitive amine oxidase(SSAO)and its possible contribution to vascular damage in Alzheimer's disease[J].J.Neur.Transm.,2007,114:857-862.
[9]HAUPTMANM M,STEWART P A,LUBIN J H,et al..Mortality from lymphohematopoietic malignancies and brain cancer among embalmers exposed to formaldehyde[J].J.Natl.Cancer Inst.,2009,101:1696-1708.
[10]TASKINEN H K,KYYRCNEN P,SALLMN M,et al..Reduced fertility among female wood workers exposed to formaldehyde[J].J.Ind.Med.,1999,36:206-212.
[11]OIBERG M T.Formaldehyde and cancer an epidemiologic perspective[J].Adv.Chem.,1985,210:289-295.
[12]CLARY J J.Formaldehyde risk analysis[J].Adv.Chem.,1985,210:341-355.
[13]GOODE J W.Toxicology of formaldehyde[J].Adv.Chem.,1985,210:217-227.
[14]THORNDIKE J,BECK W S.Production of formaldehyde from N-5-methyltetrahydrofolate by normal and leukemic leukocytes[J].Cancer Res.,1977,37:1125-1132.
[15]TSUKADA Y,FANG J,WARREN M E,et al..Histone demethylation by a family of jmjc domain-containing proteins[J].Nature,2006,439:811-816.
[16]KALSZ H.biological role of formaldehyde,and cycles related to methylation,demethylation,and formaldehyde production[J].Rev.Med.Chem.,2003,3:175-192.
[17]SONG H,RAJENDIRAN S,KIM N,et al..A tailor desinged fluorescent‘turn-on’sensor of formaldehyde based on the BODIPY motif[J].Tetrahedron Lett.,2012,53(37):4913-4916.
[18]TANG Y,KONG X,LIU Z R,et al..A Lysosome-targeted turn-on fluorescent probe for endogenous formaldehyde in living cells[J].Anal.Chem.,2016,88(19):9353-9363.