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Synthesis And Properties Of AIE Materials Based On Triped-Naphthalimide And Functionalized Pillararene

Posted on:2021-04-17Degree:MasterType:Thesis
Country:ChinaCandidate:G F GongFull Text:PDF
GTID:2381330623482105Subject:Organic Chemistry
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Aggregation-Induced Emission?AIE?was first proposed by Ben-Zhong Tang in2001.It refers to that some molecules don't emit light or emit weak light in dilute solution,but their fluorescence significantly enhance in aggregated state.Because the AIE effect is the opposite of the conventional Aggregation-Induced Quenching?ACQ?effect,and as a new luminescence phenomenon,the AIE effect has been widely favored by scientific researchers.In addition,although more and more chemosensors have been reported in recent years,the design of novel sensor for high selectively and sensitively detecting and efficiently separating the target guest have always been the focus and difficulty.It is worth mentioned that AIE will provide new ideas for the design of sensors with high selectivity and sensitivity.In view of these,this paper mainly reviews the research progress of the AIE-based fluorescent materials at home and abroad in recent years.On this basis,and based on the interests of our group in the construction of AIE-based supramolecular materials,we constructed some kinds of AIE-based supramolecular materials based on trinaphthimide and its functionalized pillar[5]arene,and further studied their applications in the detection and separation for anions and cations.Interestingly,we found and proposed two new ultra-sensitive response mechanisms,and provided effective design ideas for the construction of highly selective,ultra-responsive materials from different research perspectives.This paper will discuss the research progress,construction and performance research of AIE materials from four chapters.In chapter 1,we introduce the research progress of AIE materials based on tetraphenylethene,triphenylamine,naphthalimide,macrocyclic compounds et al in the past 20 years,and describe their applications in chemical sensors,biological imaging,organic optoelectronic materials and so on.On the basis of these studies,we summarize and put forward our research topic and design ideas.In chapter 2,we synthesized the naphthalimide-functionalized tripodamide compound TNA,and studied its response to anions and cations in solution.The study found that F-could induce sensor?TNA?to result in supramolecular polymerization and form fibrous supramolecular polymers?TNA-F?,which is accompanied by the aggregation-induced emission enhancement effect?AIEE?.In this process,the detection of F-by TNA can reach the level of ultra-sensitive detection(LOD=8.67×10-9 M).Meanwhile,the solid powder of TNA could act as an efficient adsorbing material for the removal of F-from water?adsorption rate?85%?.Interestingly,the fluorescence of the fibrous supramolecular polymer?TNA-F?was quenched after the addition of Fe3+,and the fluorescence could be recovered again after the addition of F-.This process could be continuously cycled for more than three times.Meanwhile,the test kits based on TNA and TNA-F could also conveniently and quickly detect F-and Fe3+.This method of constructing supramolecular polymer by anion induction provides an effective way for the design of supramolecular polymer and the construction of ultra-sensitive and responsive materials.In chapter 3,in order to study the assembly performance of naphthalimide-functionalized tripodamide compound TNA?renamed TC?and guest?containing electron-rich groups?,the naphthalimide-modified pillar[5]arene?SPND?was synthesized,supramolecular assembly of SPND and TC was carried out in pure DMSO solution.It was found that the pillar[5]arene group of SPND and the naphthalimide group of TC were assembled by exo-wall?-?interactions into a green fluorescent supramolecular organo-gel?ST-G?with AIE performance.Interestingly,the ST-G could achieve ultrasensitive detection of arsenite?AsO2-?in water through the competition of lone pair-?and exo-wall?interactions(LOD=1.7×10-9 M).The xerogel powder of ST-G also could serve as an adsorption material to separate AsO2-from the aqueous solution of AsO2-.Meanwhile,the ST-G based film could serve as a test kit for effectively detecting AsO2-.This competitive recognition mechanism provides a new idea for the design of ultrasensitive sensitive materials.In chapter 4,in order to study the assembly performance of naphthalimide-functionalized tripodamide compound TNA and guest?containing electron-deficient group?.We synthesized tri-?4-amino pyridine?-functionalized tripodal amide derivative guest?G?,and used TNA and G for supramolecular self-assembly.It was found that TNA and G could form stable supramolecular gel TG in DMSO/H2O system with blue fluorescence,accompanied by AIE effect.Interestingly,the TG could achieve selective detection of CN-and Fe3+,in addition,the metal organic gel TG-Fe was formed after adding Fe3+into TG,which could respond to H2PO4-selectively.The LODs of TG for CN-,Fe3+and H2PO4-are in the range of 4.93×10-9-7.80×10-8 M.In addition,the xerogel of TG could adsorb and separate Fe3+from aqueous solution,the adsorption rate is 96%.Meanwhile,the test film based on TNA and TNA-F could also conveniently and quickly detect CN-,Fe3+and H2PO4-.The experiment provides an effective way for the design of intelligent stimulus response materials and the detection of multi-analytes.
Keywords/Search Tags:Aggregation-induced emission, Naphthalimides, Pillararene, Self-assemble, Ultrasensitive detection
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