CN110563734B - 一种吩嗪三唑类化合物的合成及其识别汞离子和钴离子的应用 - Google Patents
一种吩嗪三唑类化合物的合成及其识别汞离子和钴离子的应用 Download PDFInfo
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Abstract
本发明公开了一种吩嗪三唑1H‑[1,2,3]三唑[4,5‑b]吩嗪,是以二氨基吩嗪盐酸盐和NaNO2为原料,在酸性环境中反应而得。该吩嗪三唑可以作为荧光传感器同时在含水30%的体系中对Hg2+、Co2+进行双功能检测:即在吩嗪三唑的DMSO/H2O体系中加入12种常见的重金属阳离子,只有Hg2+的加入可使主体溶液的荧光变为亮黄色,且只有Co2+的加入可使主体溶液的荧光变为蓝绿色。滴定实验表明,该吩嗪三唑对Hg2+荧光响应的最低检测限为4.96×10‑7M,对Co2+荧光响应的最低检测限为3.33×10‑8M,因而对Hg2+、Co2+的检测具有很高的灵敏度。
Description
技术领域
本发明涉及一种吩嗪三唑类化合物的合成方法,尤其涉及一种吩嗪三唑1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的合成方法;本发明同时涉及该吩嗪三唑类化合物在含水体系中双功能检测Hg2+和Co2+ 的应用,属于化学合成技术领域和离子检测领域。
背景技术
水体中的无机汞离子通过微生物的作用可以转变成剧毒的甲基汞,由食物链进人人体,引起汞中毒事件。慢性汞中毒可使人性格变得胆小怕羞、孤独、厌烦、消极抑郁、易激怒,有时行为怪僻,自觉口内有金属味,口腔黏膜充血、牙龈红肿、牙齿松动、牙龈或口颊黏膜出现色素沉着,亦可出现“汞毒性震颤”,手指、舌、眼睑震颤最为常见,严重时可蔓延至颊肌、上肢、下肢,并出现手指书写震颤。钴是维生素B12组成部分,反刍动物可以在肠道内将摄入的钴合成为维生素B12,已观察到无机钴对刺激红细胞生成有重要的作用。有种贫血用叶酸、铁、B12治疗皆无效,有人用大剂量的二氯化钴可治疗这类贫血。然而,这么大剂量钴反复应用可引起中毒。钴对红细胞生成作用的机制是影响肾释放促红细胞生成素,或者通过刺激胍循环。还观察到供给钴后可使血管扩张和脸色发红,动物实验结果显示,甲状腺素的合成可能需要钴,钴能拮抗碘缺乏产生的影响。钴元素能刺激人体骨髓的造血系统,促使血红蛋白的合成及红细胞数目的增加。大多以组成维生素B12的形式参加体内的生理作用。钴刺激造血的机制为,钴元素可抑制细胞内呼吸酶,使组织细胞缺氧,反馈刺激红细胞生成素产生,进而促进骨髓造血。钴元素可促进脾脏释放红细胞,但经常注射钴制剂或暴露于过量的原始钴环境中,可引起钴中毒。因此能够在含水体系中检测Hg2+和Co2+具有重要的意义。
吩嗪及其衍生物最早的应用是染料,接着发现它们有生物活性,可以用作杀菌剂。近年来吩嗪在医药、农药、发色体、导体和电池材料等领域的应用越来越广泛。含氮杂环化合物有着独特的生物活性,毒性低,内吸性高,常被用作医药和农药的结构组成单元,在医药和农药合成方面起着重要的作用。其中三唑类化合物作为含氮杂环的重要组成部分,因其独特的结构特征而得到广泛的应用。然而,关于吩嗪三唑类化合物在离子检测方面的应用尚未见报道。
发明内容
本发明的目的是提供一种吩嗪三唑类化合物——吩嗪三唑1H-[1,2,3]三唑 [4,5-b] 吩嗪及其合成方法;
本发明的另一目的是提供该吩嗪三唑类化合物在含水体系中双功能检测Hg2+、Co2 +的应用。
一、吩嗪三唑类化合物及其合成
吩嗪三唑1H-[1,2,3]三唑 [4,5-b] 吩嗪,标记为PHTA,结构式为:
吩嗪三唑1H-[1,2,3]三唑 [4,5-b] 吩嗪的合成:将二氨基吩嗪盐酸盐溶解于30~37%的稀盐酸,加入NaNO2和水,先在0~4℃下搅拌反应2~3h,再在100℃下搅拌反应2~3h;反应结束后抽滤,烘干,即得目标产物1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)。
二氨基吩嗪盐酸盐与NaNO2的摩尔比为1:10。
图1为上述合成的PHTA的部分核磁氢谱图,图2为PHTA的部分核磁碳谱图,图3为1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的部分质谱图。可见吩嗪三唑1H-[1,2,3]三唑 [4,5-b] 吩嗪成功合成。
二、吩嗪三唑(PHTA)作为荧光传感器双功能检测Hg2+ 和Co2+
1、溶剂的选择
将主体PHTA用各种溶剂(THF、DMSO、DMF、MeCN、MeOH、EtOH、CHCl3、CCl4)配制成10ml,2×10-4mol/L的溶液,进行荧光扫描。结果发现,DMSO配制的主体溶液的荧光最强且溶解性最好,因此我们选择DMSO为溶剂(如图4)。
2、含水量的测定
将PHTA在25 ml的试管中配置成2×10-3mol/L的PHTA水溶液(DMSO);配置4×10- 3mol/L的Hg2+和Co2+水溶液(H2O配置),用移液管取比色管中的PHTA稀释溶液0.5 ml,Hg2+和Co2+水溶液0.5 ml,分别将其配置成不同含水比的溶液(0,10%,20%,30%,40%,50%,60%,70%,80%,90%)的溶液并进行荧光扫描。结果发现,在含水30%时PHTA对Hg2+和Co2+的荧光强度最强(如图5,图6),因此,我们确定本次实验的溶剂为DMSO/H2O(7: 3,v/v)。
3、荧光检测Hg2+
将PHTA在25 ml的试管中配置成2×10-3mol/L的PHTA水溶液(DMSO),放置备用。配置4×10-3mol/L的Hg2+水溶液(用Hg(ClO4)2·3H2O,H2O配置),用移液管取比色管中的PHTA稀释溶液0.5 ml,Hg2+溶液0.5 ml,蒸馏水1 ml用DMSO定容至5 ml(此时主体PHTA溶液的浓度为2×10-4mol/L),摇晃使其反应均匀后将其溶液倒入石英比色皿中,进行荧光扫描。并用相同的方法加入,扫描Fe3+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+和 Mg2+离子的溶液。
图7为PHTA以及在PHTA加入其他的金属阳离子的荧光光谱图(λ ex=450nm)。由图7可以看出,主体PHTA自身在365 nm的紫外灯下发出微弱的黄色荧光。在加入Hg2+后其荧光迅速变为亮黄色(3s)。同时,在荧光发射光谱中也可以观察到:当激发波长为450 nm时,PHTA微弱的黄色荧光(发射波长530nm)且荧光强度最大为33a.u。当加入Hg2+后,荧光强度增加到237a.u,荧光强度大约增加了7倍。因此,该吩嗪三唑PHTA能够作为识别Hg2+的荧光传感器。
荧光滴定实验:用0~6.92当量的Hg2+对PHTA做荧光滴定,检测主体不同浓度的Hg2+对主体PHTA的荧光光谱特性的影响(图8)。结果发现,随着溶液中Hg2+浓度的增加,PHTA荧光强度逐渐增强,在加入到6.92当量的Hg2+之后荧光强度达到最大值,为245a.u,再进行滴加强度便不再变化。同时,我们根据荧光滴定曲线做出了发射波长为530nm的荧光滴定散点图(图8插图),根据此散点图用3σ/m法做出了荧光拟合曲线(图9),并且计算出了主体分子PHTA对Hg2+荧光响应的最低检测限为4.96×10-7M。
4、荧光检测Co2+
将PHTA在25 ml的试管中配置成2×10-3mol/L的PHTA水溶液(DMSO),放置备用。配置4×10-3mol/L的Co2+水溶液(用Co(ClO4)2•6H2O,H2O配置),用移液管取比色管中的PHTA稀释溶液0.5 ml,Co2+溶液0.5 ml,蒸馏水1 ml用DMSO定容至5 ml(此时主体PHTA溶液的浓度为2×10-4mol/L),摇晃使其反应均匀后将其溶液倒入石英比色皿中,进行荧光扫描。并用相同的方法加入,扫描Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Ni2+,Cd2+,Pb2+,Zn2+, Cr3+和 Mg2+离子的溶液。
图9为PHTA以及在PHTA加入其他的金属阳离子的荧光光谱图(λ ex=450 nm)。由图可以看出,主体PHTA自身在365 nm的紫外灯下发出微弱的黄色荧光,在加入Co2+后其荧光迅速变为蓝绿色(3s)。同时,在荧光发射光谱中我们也可以观察到:当激发波长为450 nm时,PHTA微弱的黄色荧光(发射波长530nm)且荧光强度最大为33 a.u。当加入Co2+后,波长移动到497 nm处,且荧光强度增加到497a.u,荧光强度大约增加了15倍。因此,该吩嗪三唑PHTA能够作为识别Co2+的荧光传感器。
荧光滴定实验:用0~1.14当量的Co2+对PHTA做荧光滴定,检测主体不同浓度的Co2+对主体PHTA的荧光光谱特性的影响(图10)。结果发现,随着溶液中Co2+浓度的增加,PHTA荧光强度逐渐增强,在加入到1.14当量的Co2+之后荧光强度达到最大值,为498a.u,再进行滴加强度便不再变化。同时,我们根据荧光滴定曲线做出了发射波长为485nm的荧光滴定散点图(图10插图),根据此散点图用3σ/m法做出了荧光拟合曲线(图11),并且计算出了主体分子PHTA对Co2+荧光响应的最低检测限为3.33×10-8M。
5、荧光传感器PHTA识别Hg2+和 Co2+的机理
图12为PHTA滴加0.01当量、0.05当量、0.1当量、0.2当量、0.5当量、1.0当量、1.5当量、2.0当量和3.0当量Hg2+的部分核磁滴定氢谱图,由图12可以看出,通过在核磁滴定实验中滴加不同当量的Hg2+,三唑环中的活泼氢Hd逐渐消失,这说明加入Hg2+后三唑环上发生了去质子化作用。吩嗪环中的质子氢Ha没有发生移动,而Hb和Hc都向低场移动,这说明Hg2+的加入在吩嗪三唑PHTA的三唑环和邻近三唑环的苯环上作用。而且在PHTA和PHTA-Hg红外光谱图上也能清楚地看到-NH峰和苯环上的-CH峰都发生了变化。图13为PHTA与Hg2+的荧光工作曲线,可以看出,拐点在0.75处,证明PHTA和Hg2+ 是以2:5的络合比进行络合的。图14和图15为PHTA与Co2+的荧光工作曲线图,可以看到,在逐渐增大Co2+的含量时分别有两个拐点在出现在0.2和0.7处,说明PHTA和Co2+在Co2+含量小时是以4:1的络合比进行络合的,而当Co2+含量大时是以2:4的络合比进行络合的。图16为PHTA、PHTA-Hg和PHTA-Co的红外光谱图,发现-NH峰和苯环上的-CH峰发生变化,也就是说明PHTA和Co2+也在三唑环和邻近三唑环的苯环上作用。图17为PHTA的XRD谱图,图18为PHTA-Hg和PHTA-Co的XRD谱图,可以知道,在加入Hg2+后PHTA分子间距增大,说明有cation-π作用存在。通过比较PHTA和PHTA-Co的XRD谱图和红外光谱图发现,在加入Co2+后PHTA分子间距也增大,说明有也存在cation-π作用。
附图说明
图1为1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的部分核磁氢谱图。
图2为1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的部分核磁碳谱图。
图3为1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的部分质谱图。
图4为PHTA在不同溶剂下的荧光光谱图。
图5为在PHTA中分别加入2倍当量的Hg2+在不同含水比下的荧光强度柱状图。
图6为在PHTA中分别加入2倍当量的Co2+在不同含水比下的荧光强度柱状图。
图7为PHTA加入不同金属阳离子的荧光全扫描光谱(λ ex=450 nm)和在紫外灯照射下的溶液荧光变化图。
图8为在PHTA加入不同当量Hg2+的荧光滴定光谱曲线以及在560 nm处的荧光散点图。
图9为PHTA和Hg2+ 在560 nm处的荧光强度拟合曲线图。
图10为PHTA加入不同当量Co2+的荧光滴定光谱曲线以及在498 nm处的荧光散点图。
图11为PHTA和Co2+在498 nm处的荧光强度拟合曲线图。
图12为PHTA对于Hg2+的部分核磁滴定氢谱图。
图13为PHTA与Hg2+的荧光工作曲线图。
图14为PHTA和Co2+以4:1络合时荧光工作曲线图。
图15为PHTA和Co2+以2:4络合时荧光工作曲线图。
图16为PHTA、PHTA-Hg和PHTA-Co的红外光谱图。
图17为PHTA的XRD谱图。
图18为PHTA-Hg和PHTA-Co的XRD谱图。
具体实施方式
下面通过具体实施例对本发明1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的合成,以及其在DMSO/H2O (7: 3, v/v)体系对Hg2+和Co2+双功能检测的方法作进一步说明。
实施例1:1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的合成
(1)2-氨基吩嗪盐酸盐的合成:按文献【B. R.Yong, T. B.Wei, W. J.Qu, Q.Lin,Y. M.ZhangandH. Yao. New J. Chem., 2018,42, 14766-14771】合成;
(2)1H-[1,2,3]三唑 [4,5-b] 吩嗪(PHTA)的合成:取100mL圆底烧瓶将1mmol(0.2121g)2-氨基吩嗪盐酸盐中加入10mL 37%稀盐酸进行溶解,再加入10mmol (0.6899 g)NaNO2,30mL水,在0℃下搅拌反应3h,溶液为深棕色,且放出有味气体。之后将溶液升温至100℃搅拌反应3h,反应放出大量气体,且颜色变为深红色;待反应结束后抽滤,烘干,得到深褐色粉末即为目标产物PHTA。产率:94.6%。产物PHTA的表征数据为:1H NMR (600MHz,DMSO-d6) δ(ppm):16.60(s,1H),8.33-8.31(dd,1H),8.24-8.22 (d,1H), 8.05-8.04(m,2H), 8.03-7.99 (m,2H).13C NMR (DMSO-d6, 150 MHz), δ/ppm:143.29, 142.26,141.83, 133.62, 132.27, 130.71,129.79.ESI-MS C12H7N5+Hcalcd for 222.0774,found 222.0773。
PHTA的合成式如下:
实施例2、在DMSO/H2O (7: 3,v/v)体系对Hg2+和Co2+双功能荧光检测
在DMSO/H2O(7: 3,v/v)体系中加入12种常见的重金属阳离子Fe3+,Hg2+,Ag+,Ca2+,Cu2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cr3+,Mg2+的水溶液,若溶液的荧光变为亮黄色,说明加入的Hg2+,若溶液的荧光变为蓝绿色,说明加入的是Co2+,否则加入的是其他金属阳离子。
Claims (2)
2.如权利要求1所述吩嗪三唑类化合物作为荧光传感器在检测Hg2+和Co2+的应用,其特征在于:DMSO/H2O 体系中,H2O的体积百分数为20~50%。
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