CN113880727B - 一种对酸性环境具有双荧光检测信号的分子传感器及应用 - Google Patents
一种对酸性环境具有双荧光检测信号的分子传感器及应用 Download PDFInfo
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Abstract
本发明提供了一种对酸性环境具有双荧光检测信号的分子传感器及应用，涉及有机功能材料检测技术领域。本发明公开的分子传感器，是以2‑氨基芴和对‑二苯胺基苯甲醛为反应原料，基于醛氨之间的亲核加成反应制备；该分子传感器同时含有二苯胺基及亚胺两类质子作用位点，其对酸性环境表现出灵敏的“关‑开‑关”双重荧光检测信号，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
本发明涉及有机材料检测功能技术领域，具体涉及一种对酸性环境具有双重荧光响应信号的三苯胺-芴单席夫碱分子传感器及其在检测领域应用。
背景技术
随着社会的发展，环境污染问题是全球共同关注的一个热点，亦是我国经济和社会可持续发展面临的主要问题之一。例如特定的pH值条件在当前工农业生产过程中具有非常重要的应用。然而当酸性或碱性过高的工业废水排放到自然界后，对土壤及整个水系的污染严重，有时会造成植物枯萎、动物死亡，给生态系统和人类生存环境造成巨大危害。此外，人体内通常通过机体体液的缓冲体系及各器官的相互调节，维持有机体内恒定的pH环境，使生物体内各功能正常进行。一旦体内pH值偏离正常水平可引起细胞失活、导致人体内正常机能紊乱，进而会引发炎症、阿尔兹海默症、恶性肿瘤等重大疾病。因此，发展高效、便捷的pH值检测方法对工农业生产、环境科学等都有重要的意义。
在诸多检测方法中，灵敏度高、成本低、易操作的荧光分子传感器受到越来越多的关注。荧光分子传感器通过巧妙设计将发生在微观世界的识别过程转换为易于检测的光学信号，在分子水平上实现了原位、实时、灵敏的检测过程。因此，荧光分子传感器成为检测各领域pH变化的强有力工具。基于不同的检测机制，人们已发明了数目众多、功能各异的pH荧光分子传感器。但目前已制备的pH荧光分子传感器检测信号大多呈单一方向变化，即随着酸性环境增强/减弱，荧光信号只是强度增加或降低；荧光信号强度随溶液酸性环境改变而呈现“关-开-关”双向变化的超灵敏分子传感器较少研究。而在人们工作、生活中对动态pH变化灵敏检测的需求越来越高，开发出快捷灵敏、易于制备、成本低的pH荧光分子传感器是当前各监测领域所迫切需求的。
芴荧光团较高的摩尔消光系数、良好的光稳定性、结构易于修饰等优点，是优良的荧光信号基团。易于合成的亚胺-C=N-基团具有较强的质子络合能力；当-C=N-基团中氮原子与质子络合后，可诱导灵敏的荧光强度或双通道光谱变化。人们通过对-C=N-基团周边的取代修饰，合成了系列具有不同识别性能及光学转变机制的荧光分子传感器[X. Ma, J.Cheng, J. Liu, X. Zhou, H. Xiang, New J. Chem., 2015, 39, 492; F. Wang, C.Li,X. Zhang,A. Wang,L. Zhou,C. Jia,J. Xu, Y. Chen, Dyes and Pigments, 2019,171, 107667]。但芴荧光团构筑、易于制备、对酸性环境具有灵敏的“关-开-关”双重荧光响应的分子传感器研究较少。
发明内容
本发明的技术目的在于提供一种对酸性环境具有双重荧光响应信号、且易于制备的三苯胺-芴单席夫碱分子传感器。
本发明的另一技术目的在于提供一种可动态检测人们工作、生活废水中酸性pH值方法，该方法具有高效、快捷、简便、灵敏、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：
一种对酸性环境具有双重荧光检测信号的三苯胺-芴单席夫碱分子传感器，其分子结构为：
一种对酸性环境具有双重荧光检测信号的三苯胺-芴单席夫碱分子传感器，制备方法如下：
在N2保护条件下，将αmmol对-二苯胺基苯甲醛、βmmol 2-氨基芴放入盛有γmL无水乙醇的圆底烧瓶后升温至回流，继续回流反应6-10小时；将反应所得混合物过滤、无水乙醇洗涤、干燥后，得到橘红色三苯胺-亚胺芴分子传感器；α:β:γ为1:1:20。
三苯胺-芴单席夫碱分子传感器的制备反应式为：
本发明具有如下技术效果：本三苯胺-芴单席夫碱分子传感器受体单元同时含有二苯胺基及亚胺两个质子作用位点，随着溶液酸性环境不断增强，该分子在384 nm位置最大荧光发射强度先明显增加然后又降低，对酸性环境呈现出灵敏的“关-开-关”双重荧光检测信号，具有较高的应用价值；本发明提供的三苯胺-芴单席夫碱分子传感器的制备过程，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，为本三苯胺-芴单席夫碱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 为三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液中加入不同浓度HCl的荧光发射光谱。
图3 为三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液中加入不同浓度HAc的荧光发射光谱。
图4 为三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液中同时加入10倍HCl和10倍不同金属离子的荧光发射光谱。
具体实施方式
本发明所公开的一种对酸性环境具有双重灵敏检测信号的三苯胺-芴单席夫碱分子传感器，其分子结构为：
其可采用2-氨基芴和对-二苯胺基苯甲醛为反应原料，通过一步聚合反应来制得，合成反应式为：
实施例1
在N2保护条件下，将1 mmol对-二苯胺基苯甲醛、1 mmol 2-氨基芴放入盛有20 mL无水乙醇的圆底烧瓶后升温至回流；继续回流反应6小时；将反应所得混合物过滤、无水乙醇洗涤、干燥后，得到橘红色粉末状化合物A，226.7 mg，产率为52%。
实施例2
在N2保护条件下，将1 mmol对-二苯胺基苯甲醛、1 mmol 2-氨基芴放入盛有20 mL无水乙醇的圆底烧瓶后升温至回流；继续回流反应10小时；将反应所得混合物过滤、无水乙醇洗涤、干燥后，得到橘红色粉末状化合物B，228.9 mg，产率为52.5%。
对实施例1-2分别获得的化合物A及B 进行分析测定，二者的核磁氢谱图一致，数据如下：在1H NMR (CDCl3, 400 MHz)中，包含1个C=N-碳上质子信号峰：8.63 (s, 1H)；21个芳香环质子信号峰：7.95 (t, 2H ), 7.87 (d, 2H ), 7.61 (d, 1H), 7.51 (s, 1H ),7.44 (t, 5H ), 7.35 (s, 1H), 7.33 (t, 1H )，7.,22 (t, 4H), 7.18 (d, 2H ), 7.02(d, 2H ),；2个CH2-质子信号峰：3.98 (s, 2H )，其与三苯胺-芴单席夫碱分子理论值基本一致。由此可确认化合物A及B的分子结构为：
实施例3
三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液水溶液对不同浓度盐酸的荧光检测性能：在浓度为2×10-5 mol/L的三苯胺-芴单席夫碱分子传感器95%乙腈水溶液里分别加入不同浓度的HCl，二者摩尔当量比分别为1:0、1:1、1:2、1:3、1:4、1:5、1:6、1:7、1:8、1:9、1:10、1:15、1:20、1:25、1:30、1:35、1:40、1:45、1:50、1:55、1:60、1:65、1:70、1:75、1:80、1:90、1:100、1:500。系统的光谱性质研究表明：随着溶液中HCl物质的量不断增加，从0→10→100倍，三苯胺-芴单席夫碱分子传感器自由状态时384 nm弱荧光发射强度先是显著增加然后又被淬灭。这些研究表明，三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液中对酸性环境具有灵敏的“关-开-关”的双荧光信号检测潜能。
实施例4
三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液对不同浓度醋酸的荧光检测性能：在浓度为2×10-5 mol/L的三苯胺-芴单席夫碱分子传感器95%乙腈水溶液里分别加入不同浓度的HAc，二者物质的量比例分别为1:0、1:2、1:4、1:6、1:8、1:10、1:12、1:16、1:20、1:30、1:40、1:50、1:60、1:70、1:80、1:90、1:100、1:200。系统的荧光发射光谱性质研究表明：随着溶液中醋酸物质的量不断增加，从0→20→200倍，三苯胺-芴单席夫碱分子传感器弱荧光发射强度先是明显增加然后又降低，甚至淬灭，表明三苯胺-芴单席夫碱分子传感器在95%乙腈水溶液里对醋酸导致的酸性环境具有灵敏的“关-开-关”双重荧光信号检测潜能。
实施例5
三苯胺-芴单席夫碱分子传感器在不同金属离子存在时对不同酸性环境的荧光检测性能：在三苯胺-芴单席夫碱分子传感器95%乙腈水溶液里加入10倍摩尔当量的盐酸后，再分别加入10倍摩尔量的K+、Na+、Ba2+、Ca2+、Mg2+、Cd2+、Hg2+、Mn2+、Ni2+、Zn2+、Co2+、Cu2+等金属离子，由其荧光发射光谱的变化可发现：10倍盐酸加入后，该荧光化合物在384 nm位置处最大荧光发射强度明显增加；K+、Na+、Ba2+、Ca2+、Mg2+、Cd2+、Hg2+、Mn2+、Ni2+、Zn2+、Co2+、Cu2+等金属离子加入三苯胺-芴单席夫碱分子传感器-HCl混合体系后，该体系强的荧光发射基本不变，表明即使在金属离子存在时，三苯胺-芴单席夫碱分子传感器对酸性环境具有良好的检测潜能。
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1.一种三苯胺-芴单席夫碱分子传感器在酸性环境检测中的非诊断性应用；其特征在于所述三苯胺-芴单席夫碱分子传感器结构如下：
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