CN113061237B - 一种苯基噻咯基共轭微孔聚合物及其制备方法、应用 - Google Patents
一种苯基噻咯基共轭微孔聚合物及其制备方法、应用 Download PDFInfo
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- CN113061237B CN113061237B CN202110331019.4A CN202110331019A CN113061237B CN 113061237 B CN113061237 B CN 113061237B CN 202110331019 A CN202110331019 A CN 202110331019A CN 113061237 B CN113061237 B CN 113061237B
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- microporous polymer
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- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 16
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Abstract
本发明公开了一种苯基噻咯基共轭微孔聚合物。本发明还公开了上述苯基噻咯基共轭微孔聚合物的制备方法，包括如下步骤：取物质A、三聚氯氰，在催化剂存在下，进行傅‑克芳基化反应，得到苯基噻咯基共轭微孔聚合物。本发明还公开了上述苯基噻咯基共轭微孔聚合物作为荧光传感材料的应用。本发明合成的苯基噻咯基共轭微孔聚合物具有良好的化学稳定性和热稳定性，且在其他物质存在的情况下，能够选择性地荧光传感邻硝基苯酚；检测方法操作简便、信号直观、灵敏度高、选择性好，可实时原位检测。
Description
技术领域
本发明涉及荧光传感检测技术领域，尤其涉及一种苯基噻咯基共轭微孔聚合物及其制备方法、应用。
背景技术
邻硝基苯酚(o-NP)是硝基苯酚的异构体之一，它对人类、动物、植物、微生物和厌氧细菌产生了显著的毒性作用，对健康构成了重大风险。其毒性被认为是由于硝基基团很容易被酶还原成硝基阴离子自由基、亚硝基和羟胺衍生物，而这些衍生物具有细胞毒性、致突变性和致癌性(J.Mol.Sci.2008,9,316–326)。邻硝基苯酚是颜料、橡胶化学品、木材防腐剂、照相化学品和杀菌剂生产中的化学中间体，具有剧毒，对生物体的生长和代谢活动有更严重的影响，甚至污染爆炸地点附近的土壤(Sensor.Actuat.B-Chem.2016,237,487–494；J.Environ.Manage.2008,86,291–296)。在低浓度下，邻硝基苯酚对水的味道和气味有不同的影响，因而引起环境方面的特别关注(Sensor.Actuat.B-Chem.2016,237,487–494；Sep.Purif.Technol.2009,70,199–206)。因此，开发一种能够快速、经济有效地检测低浓度邻硝基苯酚的新方法，是环境和健康保护的迫切需求。
人们提出了几种测定环境样品中邻硝基苯酚的仪器分析技术，包括高效液相色谱(Sensor.Actuat.B-Chem.2008,135,61–65)、紫外-可见和荧光光谱技术(Anal.Chim.Acta2001,426,185–195；Talanta 1997,44,1319–1327；J.Hazard.Mater.2007,146,421–427)、毛细管区带电泳(Talanta 2004,1,135–139)、电化学技术(Sensor.Actuat.B-Chem.2016,237,487–494；J.Environ.Manage.2008,86,291–296；Talanta 2009,1,97–102)。在上述技术中，荧光检测由于其仪器简单、成本低、快速和高灵敏度而变得非常流行(Chem.Soc.Rev.2014,43,5815–5840；J.Mater.Chem.A 2015,3,92–96；Sensor.Actuat.B-Chem.2016,226,273–278；New J.Chem.2014,38,5695–5699)。
共轭微孔聚合物(CMPs)是重要的一类多孔有机聚合物，由于具有永久的多孔性和扩展的共轭体系，在荧光传感邻硝基苯酚中具有潜在的应用前景。之前，我们课题组制备了一些共轭微孔聚合物，并研究了它们对邻硝基苯酚的荧光传感性能。如三苯胺基共轭微孔聚合物(Sensor.Actuat.B-Chem.2017,244,334–343；J.Mater.Chem.A 2017,5,7612–7617；J.Mater.Chem.A,2018,6,2808–2816；Environ.Sci.Pollut.Res.2020,27(16),20235–20245；Eur.Polym.J.2019,115,37–44)、苯醌基共轭微孔聚合物(Micropor.Mesopor.Mat.2016,231,92–99)、含苝荧光基团的共轭微孔聚合物(J.Macromol.Sci.A 2019,56(11),1004–1011；New J.Chem.2020,44,19663–19671)、含聚集诱导发光(AIE)基团——四苯基噻吩基共轭微孔聚合物(Polym.Chem.2018,9,777–784)。
噻咯是一组五元硅环，具有特别低的最低未占分子轨道(LUMO)能级和σ*–π*共轭结构(J.Am.Chem.Soc.1996,118,11974)。噻咯表现出一些吸引人的特点，如具有较高的电子接受性、快速的电子迁移率、聚集诱导发光和高度有效的光致发光等(J.Inorg.Organomet.Polym.2009,19,249)。最近的研究表明，噻咯已经成为有价值的芳香杂环来构建各种功能聚合物。一些噻咯小分子不可能实现的新的化学性能和物理性能，可用含噻咯基聚合物来实现(J.Inorg.Organomet.Polym.2009,19,249)。六苯基噻咯(hexaphenyl-silole)具有聚集诱导发射效应(J.Mater.Chem.2012,22,6374–6382)。蒋加兴等制备了苯基噻咯基超交联有机聚合物网络，能捕获CO2(Polymer 2014,55,5746-5750；J.Appl.Polym.Sci.2018,135,45907)。但目前尚未见到苯基噻咯基共轭微孔聚合物的有关报道。
发明内容
基于背景技术存在的技术问题，本发明提出了一种苯基噻咯基共轭微孔聚合物及其制备方法、应用，本发明扩大现有共轭微孔聚合物的品种，本发明设计合成的苯基噻咯基共轭微孔聚合物具有良好的化学稳定性和热稳定性，且在其他物质存在的情况下，能够选择性地传感邻硝基苯酚；检测方法操作简便、信号直观、灵敏度高、选择性好，可实时原位检测。
本发明提出了一种苯基噻咯基共轭微孔聚合物，其结构如式(I)、式(II)或式(III)所示：
本发明还提出了上述苯基噻咯基共轭微孔聚合物的制备方法，包括如下步骤：取物质A、三聚氯氰，在催化剂存在下，进行傅-克芳基化反应，得到苯基噻咯基共轭微孔聚合物，其中，物质A的结构式如以下结构式中的至少一种：
优选地，在惰性气体氛围中进行傅-克芳基化反应。
优选地，傅-克芳基化反应的温度为40-100℃。
优选地，傅-克芳基化反应的时间为5-30h。
优选地，催化剂、物质A、三聚氯氰的摩尔比为(1-99):(0.139-13.75):(0.278-27.5)。
优选地，催化剂为三氯化铝、三氟化硼、三溴化铁中的至少一种。
优选地，反应溶剂为二氯甲烷、1,2-二氯乙烷、氯仿中的至少一种。
上述傅-克芳基化反应后，提纯得到苯基噻咯基共轭微孔聚合物，提纯方法为：傅-克芳基化反应后，固液分离，洗涤固体，抽提，干燥得到苯基噻咯基共轭微孔聚合物；干燥方式优选真空干燥，干燥温度优选50-120℃；抽提时间可以为24h等。
上述洗涤、抽提用溶剂可以为甲醇、氯仿等。
本发明还提出了上述苯基噻咯基共轭微孔聚合物作为荧光传感材料的应用。
优选地，所述苯基噻咯基共轭微孔聚合物作为荧光传感材料用于选择性荧光传感邻硝基苯酚。
有益效果：
本发明制得的苯基噻咯基共轭微孔聚合物具有良好的化学稳定性和热稳定性，并且具有优异的荧光性质，在其它硝基芳香族化合物(简称NACs)、苯酚和单质碘存在的情况下，能够选择性地传感邻硝基苯酚；检测方法操作简便、信号直观、灵敏度高、选择性好，可实时原位检测。
附图说明
图1为实施例1中苯基噻咯基共轭微孔聚合物的激发光谱和发射光谱图。
图2为实施例1中苯基噻咯基共轭微孔聚合物荧光传感不同物质的相对荧光强度(I0/I)对比柱状图。
图3为实施例1中苯基噻咯基共轭微孔聚合物荧光传感邻硝基苯酚在紫外灯下的荧光效果图。
图4为实施例1中苯基噻咯基共轭微孔聚合物对邻硝基苯酚的选择性荧光传感。
图5为实施例1中苯基噻咯基共轭微孔聚合物对邻硝基苯酚选择性荧光传感的荧光效果图。
具体实施方式
下面，通过具体实施例对本发明的技术方案进行详细说明。
实施例1
一种苯基噻咯基共轭微孔聚合物的制备方法，包括如下步骤：
将六苯基噻咯(0.8081g，1.5mmol)，三聚氯氰(0.5532g，3mmol)，无水AlCl3(1.4401g，10.8mmol)加入到无水二氯甲烷(30mL)中，在室温条件下搅拌均匀；并且通上氮气，置于油浴中加热到60℃，反应24h，然后冷却至室温，抽滤，固体产物用甲醇、氯仿各洗3遍，再用甲醇、氯仿在索氏提取器中各抽提取24h，最后在真空干燥箱中50℃干燥，得到苯基噻咯基共轭微孔聚合物，记为THPS。
实施例2
一种苯基噻咯基共轭微孔聚合物的制备方法，包括如下步骤：
将1,1-二甲基-2,3,4,5-四苯基噻咯(0.6219g，1.5mmol)，三聚氯氰(0.3690g，2mmol)，无水AlCl3(1.4401g，10.8mmol)加入到氯仿(30mL)中，在室温条件下搅拌均匀；并且通上氮气，置于油浴中加热到80℃，反应20h，然后冷却至室温，抽滤，固体产物用甲醇、氯仿各洗3遍，再用甲醇、氯仿在索氏提取器中各抽提取24h，最后在真空干燥箱中60℃干燥，得到苯基噻咯基共轭微孔聚合物，记为TTPS。
实施例3
一种苯基噻咯基共轭微孔聚合物的制备方法，包括如下步骤：
将1-甲基-1,2,3,4,5-五苯基噻咯(0.7150g，1.5mmol)，三聚氯氰(0.4613g，2.5mmol)，无水AlCl3(1.4401g，10.8mmol)加入到无水二氯乙烷(30mL)中，在室温条件下搅拌均匀；并且通上氮气，置于油浴中加热到100℃，反应16h，然后冷却至室温，抽滤，固体产物用甲醇、氯仿各洗3遍，再用甲醇、氯仿在索氏提取器中各抽提取24h，最后在真空干燥箱中100℃干燥，得到苯基噻咯基共轭微孔聚合物，记为TPPS。
实验1
取实施例1制得的苯基噻咯基共轭微孔聚合物THPS进行检测，结果如图1所示，图1为实施例1中苯基噻咯基共轭微孔聚合物的激发光谱和发射光谱图。
由图1可以看出，实施例1制得的苯基噻咯基共轭微孔聚合物THPS的发射光谱的激发波长为392nm时，发射光谱的最大吸收峰为509nm。
实验2
取实施例1制得的苯基噻咯基共轭微孔聚合物，对单质碘、硝基芳香族化合物(简称NACs)、苯酚(PhOH)进行荧光传感，其中，硝基芳香族化合物有：邻硝基苯酚(o-NP)、间二硝基苯(m-DNB)、硝基苯(NB)、对硝基甲苯(p-NT)、苦味酸(PA)、对二硝基苯(p-DNB)、二硝基甲苯(DNT)、2,4-二硝基苯酚(DNP)、间硝基苯酚(m-NP)、对硝基苯酚(p-NP)。
具体检测方法为：
S1、使用荧光分光光度计，测定浓度为0.2mg/mL苯基噻咯基共轭微孔聚合物THPS的1,4-二氧六环分散液的荧光发射光谱，通过不断地激发-发射过程，找到最佳激发波长λex＝375nm，并记录荧光发射光谱和其最高发射峰处的荧光强度记作I0；
S2、取适量浓度为0.1mol/L的单质碘、硝基芳香族化合物或苯酚溶液滴加到浓度为0.2mg/mL苯基噻咯基共轭微孔聚合物THPS的1,4-二氧六环分散液中，混合均匀，使分散液中单质碘、硝基芳香族化合物或苯酚的浓度为1.0×10-3mol/L，在相同激发波长下，测试荧光发射光谱，并记录荧光发射光谱和其最高发射峰处的荧光强度记作I；结果如图2所示，图2为实施例1中苯基噻咯基共轭微孔聚合物荧光传感不同物质的相对荧光强度(I0/I)对比柱状图。
由图2可以看出，除碘、苦味酸和2,4-二硝基苯酚外，其他物质对苯基噻咯基共轭微孔聚合物THPS荧光淬灭较小。表明苯基噻咯基共轭微孔聚合物对邻硝基苯酚有较好的选择性。
实验3
取实施例1制得的苯基噻咯基共轭微孔聚合物THPS，配置浓度为0.2mg/mL的1,4-二氧六环分散液，加入邻硝基苯酚，使邻硝基苯酚浓度为1.0×10-3mol/L；用波长为365nm紫外灯照射添加邻硝基苯酚前后的分散液，结果如图3所示，图3为实施例1中苯基噻咯基共轭微孔聚合物荧光传感邻硝基苯酚在紫外灯下的荧光效果图，其中，THPS为苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液，THPS+o-NP为添加邻硝基苯酚的苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液。
从图3中可直接观察到，邻硝基苯酚能明显地淬灭苯基噻咯基共轭微孔聚合物的荧光。
实验4
取实施例1制得的苯基噻咯基共轭微孔聚合物THPS，配置浓度为0.2mg/mL的1,4-二氧六环分散液，分别添加邻硝基苯酚、其他硝基芳香族化合物、苯酚或碘，使邻硝基苯酚、其他硝基芳香族化合物、苯酚或碘的浓度为1.0×10-3mol/L，然后在375nm的激发波长下，测定各溶液的荧光发射光谱，其中，其他硝基芳香族化合物为p-NT、DNT、DNP、m-NP、p-NP、m-DNB、p-DNB、NB、PA。
结果如图4所示，图4为实施例1中苯基噻咯基共轭微孔聚合物对邻硝基苯酚的选择性荧光传感，其中，THPS为苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液，THPS+其他NACs/I2/PhOH为添加其他硝基芳香族化合物、碘或苯酚的苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液，THPS+其他NACs/I2/PhOH+o-NP为添加其他硝基芳香族化合物、碘或苯酚，以及添加邻硝基苯酚的苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液。
从图4可以看出，当加入1.0×10-3mol/L其他硝基芳香族化合物、苯酚或碘时，苯基噻咯基共轭微孔聚合物荧光强度变化较小，但是当加入1.0×10-3mol/L邻硝基苯酚时，苯基噻咯基共轭微孔聚合物荧光强度明显降低。表明苯基噻咯基共轭微孔聚合物在其他硝基芳香族化合物、苯酚或碘存在下能选择性地荧光传感邻硝基苯酚。
用紫外灯照射上述实验4所述各分散液，结果如图5所示，图5为实施例1中苯基噻咯基共轭微孔聚合物对邻硝基苯酚选择性荧光传感的荧光效果图，其中，THPS为苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液，THPS+NACs/I2/PhOH为添加其他硝基芳香族化合物、碘或苯酚的苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液，THPS+NACs/I2/PhOH+o-NP为添加其他硝基芳香族化合物、碘或苯酚，以及添加邻硝基苯酚的苯基噻咯基共轭微孔聚合物的1,4-二氧六环分散液。
从图5可以直观地看出，其他硝基芳香族化合物、苯酚和碘不能淬灭苯基噻咯基共轭微孔聚合物的荧光，而邻硝基苯酚在上述分析物存在下，能选择性地淬灭苯基噻咯基共轭微孔聚合物的荧光。
上述实验中，苯基噻咯基共轭微孔聚合物材料的分散液的浓度可以为0.1-1.0mg/mL；荧光分光光度计的测试电压可以为220-700V，狭缝宽度可以为5-20nm。
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。
Claims (10)
1.一种苯基噻咯基共轭微孔聚合物，其特征在于，其结构如式(I)、式(II)或式(III)所示：
2. 一种如权利要求1所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，包括如下步骤：取物质A、三聚氯氰，在催化剂存在下，进行傅-克芳基化反应，得到苯基噻咯基共轭微孔聚合物，其中，物质A的结构式如以下结构式中的至少一种：
3.根据权利要求2所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，在惰性气体氛围中进行傅-克芳基化反应。
4.根据权利要求2或3所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，傅-克芳基化反应的温度为40-100 ℃。
5. 根据权利要求2或3所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，傅-克芳基化反应的时间为5-30 h。
6.根据权利要求2或3所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，催化剂、物质A、三聚氯氰的摩尔比为(1-99): (0.139-13.75): (0.278-27.5)。
7.根据权利要求2或3所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，催化剂为三氯化铝、三氟化硼、三溴化铁中的至少一种。
8.根据权利要求2或3所述苯基噻咯基共轭微孔聚合物的制备方法，其特征在于，反应溶剂为二氯甲烷、1,2-二氯乙烷、氯仿中的至少一种。
9.一种如权利要求1所述苯基噻咯基共轭微孔聚合物作为荧光传感材料的应用。
10.根据权利要求9所述苯基噻咯基共轭微孔聚合物作为荧光传感材料用于选择性荧光传感邻硝基苯酚。
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| DE10234188A1 (de) * | 2002-07-26 | 2004-02-12 | Infineon Technologies Ag | Oktupolare Moleküle als organische Halbleiter |
| WO2004058841A2 (en) * | 2002-10-05 | 2004-07-15 | The Regents Of The University Of California | Synthesis and use of inorganic polymer sensor for detecting nitroaromatic compounds |
| WO2005103653A1 (fr) * | 2004-04-09 | 2005-11-03 | Commissariat A L'energie Atomique | Capteurs chimiques comprenant des polymeres conjugues fluorescents comme materiaux sensibles, et leur utilisation pour la detection ou le dosage de composes nitres |
| JP2019172608A (ja) * | 2018-03-28 | 2019-10-10 | 三菱ケミカル株式会社 | １，３，５−トリアジン化合物、該化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
| CN110504106A (zh) * | 2019-08-14 | 2019-11-26 | 辽宁大学 | 一种基于傅-克反应的π-共轭多孔碳材料及其制备方法和应用 |
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| DE10234188A1 (de) * | 2002-07-26 | 2004-02-12 | Infineon Technologies Ag | Oktupolare Moleküle als organische Halbleiter |
| WO2004058841A2 (en) * | 2002-10-05 | 2004-07-15 | The Regents Of The University Of California | Synthesis and use of inorganic polymer sensor for detecting nitroaromatic compounds |
| WO2005103653A1 (fr) * | 2004-04-09 | 2005-11-03 | Commissariat A L'energie Atomique | Capteurs chimiques comprenant des polymeres conjugues fluorescents comme materiaux sensibles, et leur utilisation pour la detection ou le dosage de composes nitres |
| JP2019172608A (ja) * | 2018-03-28 | 2019-10-10 | 三菱ケミカル株式会社 | １，３，５−トリアジン化合物、該化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
| CN110504106A (zh) * | 2019-08-14 | 2019-11-26 | 辽宁大学 | 一种基于傅-克反应的π-共轭多孔碳材料及其制备方法和应用 |
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