CN113121385B - 一种可检测水中Fe3+、Al3+、Cu2+及Zn2+荧光分子传感器及应用 - Google Patents
一种可检测水中Fe3+、Al3+、Cu2+及Zn2+荧光分子传感器及应用 Download PDFInfo
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Abstract
本发明涉及有机化合物检测性能技术领域,公开了一种对水中Fe3+、Al3+、Cu2+及Zn2+四个金属离子具有不同光学检测信号的水杨‑芴分子传感器,其是以2,7二氨基芴和2,4‑二羟基苯甲醛为反应原料,通过一步缩合反应制备。由于该分子传感器内羟基与邻位亚胺基团双作用位点对金属离子展现较强的配位性能,结合其间烯醇异构互变特征,水杨‑芴分子对不同类型水中Fe3+、Al3+、Cu2+及Zn2+表现出不同的荧光检测信号,灵敏度高、选择性好,具有显著的应用价值;且其制备方法具有产率高、合成工艺简单,易于实施等优点,适合工业化推广,为本水杨‑芴分子传感器的推广应用创造了有利条件。
Description
技术领域
本发明涉及有机化合物检测性能技术领域,具体涉及一种可分析检测水中Fe3+、Al3+、Cu2+及Zn2+四个金属离子的多功能荧光分子传感器及其应用。
背景技术
水是人类生命的源泉,在自然界和人类的生存发展中有着举足轻重的位置。随着全球经济的迅猛发展,人类对水的需求量越来越大,但水资源的污染问题却越发严重,尤其是水资源中的重金属污染。重金属污染具有隐蔽性、长期性、积累性及不可逆性等特点,加上重金属毒性较大且在生物链中易于富集和扩大,因此水资源的重金属污染很大程度上已经危害到生态环境和人类的生存发展。重金属含量超标的污水灌溉土地后,不仅会导致农作物产量和质量下降,甚至会使植物枯萎、死亡;而进入到土壤中的重金属不能被分解或消失,但很容易被生物体内吸收,引起食物污染。被重金属污染的水及食物一旦被人们饮食后,重金属离子便可在体内不断累积,给人体造成严重伤害。如铁是人体必需的微量元素之一,但体内铁离子过多会引起肝功能异常、心肌损伤和糖尿病、肿瘤、骨质疏松等;脑组织内铝沉积过多,可使人记忆力减退、智力低下、行动迟钝;锌是参与免疫功能的一种重要元素,但是锌过量可抑制吞噬细胞的活性和杀菌力、降低人体免疫功能、使抗病能力减弱从而对疾病易感性增加;当人体内残存了大量铜之后,可导致新陈代谢紊乱、肝硬化、肝腹水甚至更为严重等等。因此,发展快速、便捷、灵敏的水中重金属离子检测方法对工农业生产、环境科学、生命科学等具有非常重要的意义。
目前,在水中重金属离检测领域,原子吸收光谱法、原子荧光光谱法、电感耦合等离子体法、电化学法等已被人们广泛使用。但该类检测方法样品一般需特殊处理,且所需检测耗时。荧光分子传感器因其灵敏度高、选择性好、成本低、易操作等特性,在环境科学检测等相关领域已得到越来越广泛的应用。荧光分子传感器通过巧妙设计,将发生在微观世界的分子识别信息转换为易于检测的光学信号,在分子水平上进行实时检测,结果精确、灵敏。人们基于不同的光学信号转换机制,已设计制备了数目众多、功能各异的金属离子荧光分子传感器。但目前大部分荧光分子传感器仅针对某一特定金属离子呈现灵敏的检测功能,功能较为单一,应用局限较大;且其具有制备工艺步骤复杂、产率低、成本高等技术不足,难以满足日益增长的市场需求。
芴荧光团具有高度共轭的刚性共平面结构,具有较高的光稳定性、结构易于修饰等优点,是优良的荧光信号基团;水杨醛腙的酚羟基与邻位亚胺基团之间烯醇互变异构可增加分子传感器灵敏度,使其与金属离子作用后导致超灵敏的光谱信号变化。鉴于此,刘菲课题组制备了鉴别Zn2+/Fe3+的芴荧光分子探针[J. Zhang, Z. Zhao, H. Shang, Q. Liu,F. Liu, New J. Chem., 2019, 43, 14179]; 陈玉婷等以冠醚为识别基团,制备了分析Cu2+/Fe3+/Mg2+的芴荧光分子探针[ F. Wang, C. Li,X. Zhang,A. Wang,L. Zhou,C. Jia,J. Xu, Y. Chen, Dyes and Pigments, 2019, 171, 107667]等等。但目前,芴-水杨醛构筑的、对水中四种金属离子具有灵敏检测功能的荧光分子传感器还没有被开发。
发明内容
本发明的技术目的在于提供一种对Fe3+、Al3+、Cu2+及Zn2+四种金属离子具有不同光学检测信号、且易于制备的水杨-芴荧光分子传感器。
本发明的另一技术目的在于提供一种可灵敏检测不同类型水中Fe3+、Al3+、Cu2+及Zn2+离子的方法,该方法具有灵敏、快速、简捷、易操作等优势。
为实现上述技术目的,本发明采用如下技术方案:
一种对Fe3+、Al3+、Cu2+及Zn2+离子具有不同光学检测信号的水杨-芴荧光分子传感器,其分子结构为:
一种对Fe3+、Al3+、Cu2+及Zn2+离子具有不同光学检测信号的水杨-芴荧光分子传感器,其制备方法如下:
将αmmol的2,4-二羟基苯甲醛、βmmol 2,7二氨基芴依次放入盛有δ mL无水乙醇的圆底烧瓶,随后加入γμL冰醋酸;升温至回流反应4-6小时;将反应所得混合物过滤、无水乙醇洗涤、干燥后,得到橘红色水杨-芴荧光分子传感器;α:β:γ: δ为2:1: 20:100。
水杨-芴分子传感器的制备反应式为:
本发明具有如下技术效果:本水杨-芴荧光分子传感器的酚羟基与邻位亚胺双重作用位点协同对金属离子具有较强的配位能力,结合其分子内的烯醇互变异构可增加分子传感器灵敏度,使其对Fe3+、Al3+、Cu2+及Zn2+离子展现出显著不同的荧光检测信号,选择性好、灵敏度高、具有较高的应用价值;本发明提供的水杨-芴荧光分子传感器制备过程,具有产率高、合成条件温和、制备工艺简单等优点,适合工业化实施,为本水杨-芴荧光分子传感器的推广应用创造了有利条件。
附图说明
图 1为实施例1-2所得化合物的核磁氢谱图。
图2为水杨-芴分子传感器在60%的二甲基亚砜蒸馏水溶液中对不同金属离子后的紫外吸收检测性能。
图3为水杨-芴分子传感器在60%的二甲基亚砜蒸馏水溶液中对不同金属离子后的荧光发射检测性能。
图4为水杨-芴分子传感器对自来水中Fe3+、Al3+、Cu2+及Zn2+的荧光检测性能。
图5为水杨-芴分子传感器对河水中Fe3+、Al3+、Cu2+及Zn2+的荧光检测性能。
具体实施方式
本发明所公开的一种对Fe3+、Al3+、Cu2+及Zn2+四种金属离子具有不同光学检测信号的水杨-芴荧光分子传感器,其分子结构为:
其可采用2,4-二羟基苯甲醛和2,7二氨基芴为反应原料,通过一步聚合反应来制得,合成反应式为:
实施例1
化合物A的制备:将2 mmol的2,4-二羟基苯甲醛、1 mmol 2,7二氨基芴依次放入盛有20 mL无水乙醇的圆底烧瓶,随后加入100 μL冰醋酸,升温至回流反应4小时;将反应所得混合物过滤、无水乙醇洗涤、干燥后,得到橘红色状化合物A,270 mg,产率为62%。
实施例2
化合物B的制备:将2 mmol的2,4-二羟基苯甲醛、1 mmol 2,7二氨基芴1 mmol 2,7二氨基芴依次放入盛有20 mL无水乙醇的圆底烧瓶,随后加入100 μL冰醋酸,升温至回流反应6小时;将反应所得混合物过滤、无水乙醇洗涤、干燥后,得到橘红色状化合物B,274 mg,产率为63%。
对实施例1、2分别获得的化合物A、B进行分析测定,二者核磁氢谱图一致,数据如下:在1H NMR (DMSO-d6, 400 MHz)中,包含4个OH质子信号峰:13.71 (s, 2H),10.28 (s,2H);2个C=N-碳上质子信号峰:8.91 (s, 2H);12个芳香环质子信号峰:7.95 (d, 2H ),7.61 (s, 2H ), 7.46 (m, 4H), 6.42 (d, 2H ),6.30 (s, 2H );2个芴基团上CH2-质子信号峰:4.00 (s, 2H ),其与水杨-芴化合物理论值基本一致。由此可确认化合物A、B的分子结构为:
实施例3
水杨-芴分子在60%DMSO蒸馏水溶液中对不同金属离子的紫外分析检测功能:在60%DMSO蒸馏水溶液中,浓度为2×10-5 mol/L的水杨-芴分子传感器最大吸收在392 nm附近;加入10倍摩尔量的Zn2+后,其最大吸收峰红移到402 nm位置附近并伴随着吸光度稍微增加; 10倍摩尔量Cu2+加入后,该分子在392 nm位置附近最大吸收稍微降低并红移到395 nm,同时其在290 nm位置附近吸收明显增加;加入Al3+离子后,该分子在392 nm位置附近最大吸收消失,同时在283 nm位置附近出现一新的强吸收;10倍摩尔量Fe3+离子加入后,该分子在392 nm位置附近最大吸收消失,同时在270-315 nm范围内出现一宽的吸收;其它金属离子如Co2+、Hg2+、Ag+、Mn2+、Ni2+、Cd2+、Li+、Na+、K+、Ba2+、Ca2+、Mg2+等加入后,该化合物在392 nm位置处最大吸收峰几乎没有明显变化。这些数据表明水杨-芴分子传感器对Fe3+、Al3+、Cu2+及Zn2+离子具有不同的紫外吸收检测潜能。
实施例4
水杨-芴分子在60%DMSO蒸馏水溶液中对不同金属离子的荧光检测性能:在60%DMSO蒸馏水溶液中,浓度为2×10-5 mol/L的水杨-芴分子传感器在512 nm位置附近有一最大荧光发射峰;加入10倍量的Zn2+后,其在512 nm位置的最大荧光发射蓝移到505 nm位置附近,荧光发射强度增加1.2倍;Al3+加入后,其最大荧光发射蓝移到415 nm位置附近,荧光强度增加1.9倍;加入Fe3+后,其在512 nm处最大荧光发射峰蓝移至414 nm处,但荧光发射强度降低; Cu2+加入后,其在512 nm处最大荧光发射峰蓝移至436 nm处,且荧光发射几乎被淬灭;其它金属离子如Co2+、Hg2+、Ag+、Mn2+、Ni2+、Cd2+、Li+、 Na+、K+、Ba2+、Ca2+、Mg2+等加入后,该化合物在512 nm位置处最大荧光发射几乎没有明显的变化。这些数据表明水杨-芴分子传感器对Fe3+、Al3+、Cu2+及Zn2+离子具有显著不同的荧光信号响应,具有识别这四种金属离子的潜能。
实施例5
水杨-芴分子传感器对自来水中Fe3+、Al3+、Cu2+及Zn2+离子的荧光检测性能:取一定体积的自来水样,用原子吸收光谱仪测定其不含Fe3+、Al3+、Cu2+、Zn2+等金属离子后,将其与DMSO配成60%DMSO自来水溶液待用。先将适量水杨-芴分子溶解在60%DMSO自来水溶液中,配成浓度为2×10-5 mol/L水杨-芴溶液;2分钟后其荧光发射光谱测试表明,水杨-芴分子在512 nm位置附近有一最大荧光发射峰;10倍摩尔当量Zn2+加入后,水杨-芴分子在512 nm位置的最大荧光发射蓝移到505 nm位置附近,荧光发射明显增强; Al3+加入后,其最大荧光发射蓝移到415 nm位置附近,荧光发射强度明显增加;Fe3+加入后,水杨-芴分子在512 nm处最大荧光发射峰蓝移至414 nm处,并伴随着荧光发射强度降低; Cu2+加入后,其在512 nm处最大荧光发射峰蓝移至436 nm处,且荧光发射显著降低。这些数据表明水杨-芴分子传感器对自来水中Fe3+、Al3+、Cu2+及Zn2+离子具有灵敏的荧光检测潜能。
实施例6
水杨-芴分子对河水中Fe3+、Al3+、Cu2+及Zn2+离子的荧光检测性能:从徒骇河中取一定体积的水样,用原子吸收光谱仪测定其不含Fe3+、Al3+、Cu2+、Zn2+等金属离子后,将其配成60%DMSO河水溶液待用。先将适量水杨-芴分子溶解在60%DMSO河水溶液中,配成浓度为2×10-5 mol/L水杨-芴溶液;2分钟后测试荧光发射光谱,发现水杨-芴分子在512 nm位置附近有一最大荧光发射峰;加入10倍Zn2+后,水杨-芴分子在512 nm位置的最大荧光发射蓝移到505 nm位置附近,荧光发射明显增强;加入Al3+后,其最大荧光发射蓝移到415 nm位置附近,荧光发射强度明显增加;Fe3+加入后,水杨-芴分子在512 nm处最大荧光发射峰蓝移至414nm处,并伴随着荧光发射强度降低; Cu2+加入后,其在512 nm处最大荧光发射峰蓝移至436nm处,且荧光发射显著降低。这些数据表明水杨-芴分子传感器对河水中Fe3+、Al3+、Cu2+及Zn2+离子具有灵敏的荧光检测潜能。
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