本文選題：水楊醛類席夫堿 + 分子內(nèi)氫鍵　； 參考：《渤海大學(xué)》2017年碩士論文

【摘要】：近年來出現(xiàn)了一種新型的分子,在高濃度狀態(tài)下能夠發(fā)出強(qiáng)的熒光,這類分子統(tǒng)稱為聚集誘導(dǎo)發(fā)光(AIE)分子,其具有很好的聚集態(tài)熒光效率,因此在新型的發(fā)光材料和生物傳感器等領(lǐng)域有著非常廣闊的應(yīng)用前景。Tong課題組發(fā)現(xiàn)具有AIE性質(zhì)的水楊醛類席夫堿化合物,可以形成分子內(nèi)氫鍵組成六元環(huán)結(jié)構(gòu)。我們以此為出發(fā)點(diǎn)設(shè)計(jì)合成了水楊醛類與鄰羥基胺類席夫堿衍生物,其同樣具有良好的聚集誘導(dǎo)發(fā)光的性質(zhì),并且能夠?qū)N-,Al~(3+),Zn~(2+),Mg~(2+),Fe~(3+),Cr~(3+),Cu~(2+)離子具有很好的識(shí)別能力,因此獲取了一些有意義的實(shí)驗(yàn)結(jié)果:1、以1-萘甲醛和鄰氨基苯硫酚為底物制備了席夫堿L1。通過熒光信號(hào)的改變發(fā)現(xiàn)探針分子L1在二甲基亞砜(DMSO)溶劑中對(duì)鐵離子具有很好的選擇性,同時(shí)還具有良好的抗干擾能力。2、以9-蒽甲醛和2-氨基4-硝基苯酚為原料合成了席夫堿L2。通過調(diào)控溶劑體系中水的含量檢測(cè)L2的熒光信號(hào)變化,結(jié)果證明分子L2具有很好的聚集熒光增強(qiáng)的性質(zhì)(AIE),同時(shí)在乙醇和水混合體系中(3:7)能夠高效選擇性識(shí)別CN-,表現(xiàn)出熒光增強(qiáng)。檢測(cè)限為1.02×10-4 M,并且不受其它離子的干擾,具有很好的選擇性。3、用鄰氨基苯酚分別與5-氯水楊醛與5-溴水楊醛反應(yīng)合成了席夫堿L3和L4。改變?nèi)軇w系中水的含量,比較熒光信號(hào)的改變,結(jié)果表明L3和L4都具有AIE性質(zhì)。在純水體系中L3對(duì)Zn~(2+)具有很好的識(shí)別能力,表現(xiàn)為熒光信號(hào)增強(qiáng),通過1:1結(jié)合方式,檢測(cè)限為4.51×10-5 M。同時(shí)在純水體系中L4對(duì)Al~(3+)具有較好的選擇性,表現(xiàn)為熒光增強(qiáng)現(xiàn)象,結(jié)合模式為1:1,其它離子對(duì)L4識(shí)別Al~(3+)沒有干擾,檢測(cè)限為5.21×10-5 M。4、以2-氨基苯并咪唑分別與5-甲基水楊醛和5-溴水楊醛反應(yīng)制備了席夫堿L5和L6,實(shí)驗(yàn)結(jié)果證明L5和L6均具有聚集熒光增強(qiáng)的性質(zhì),而且在乙醇溶劑中L5對(duì)鋅離子具有良好的識(shí)別能力并發(fā)出強(qiáng)的熒光;而在DMSO中L6能夠選擇性識(shí)別Mg~(2+),通過1:1的方式結(jié)合,檢測(cè)限達(dá)到了3.49×10-5 M。5、利用2-羥基-1-萘甲醛分別和2-(4-氨基苯基)苯并噻唑,2-(2-羥基-4-氨基苯基)苯并噻唑反應(yīng)合成了席夫堿L7和L8,研究在不同水含量體系中L7和L8的熒光變化,發(fā)現(xiàn)L7和L8都具有AIE性質(zhì)。在DMSO中,L7可以高效識(shí)別三價(jià)離子(Al~(3+),Fe~(3+),Cr~(3+)),以1:1模式結(jié)合,且識(shí)別三價(jià)離子不受其他離子干擾,檢測(cè)限分別達(dá)到了1.49×10-5 M(Al~(3+)),2.88×10-5 M(Cr~(3+)),2.12×10-5 M(Fe~(3+))。在DMSO與水的混合體系中(1:1),L8通過1:1結(jié)合有效的識(shí)別Cu~(2+),且其不受其它離子的干擾影響,具有很好的抗干擾能力,檢測(cè)限達(dá)到了1.48×10~(-6) M。
[Abstract]:In recent years, a new type of molecule has emerged, which can emit strong fluorescence at high concentration. This kind of molecule is called agglomeration induced luminescence (AIEs) molecule, and it has good fluorescence efficiency of aggregation state.Therefore, the new luminescent materials and biosensors have a very broad application prospect. Tong team found that salicylaldehyde Schiff base compounds with AIE properties can form intramolecular hydrogen bonds to form six-member ring structures.Therefore, some significant experimental results were obtained, and Schiff base L1 was prepared by using 1-naphthalene formaldehyde and o-aminophenol as substrates.By changing the fluorescence signal, it was found that the probe molecule L1 had a good selectivity for iron ion in the solvent of dimethyl sulfoxide (DMSO), and also had good anti-interference ability .2.Schiff base L _ 2 was synthesized from 9-anthracene formaldehyde and 2-amino-4-nitrophenol.By adjusting the water content in solvent system to detect the change of fluorescence signal of L2, the results show that L2 has the property of agglomeration and fluorescence enhancement. At the same time, the molecular L2 can selectively recognize CN-in ethanol and water mixture system with 3: 7) and exhibit fluorescence enhancement.The detection limit is 1.02 脳 10 ~ (-4) M, and it has good selectivity. The Schiff base L _ 3 and L _ 4 were synthesized by the reaction of o-aminophenol with 5-chlorosalicylaldehyde and 5-bromosalicylaldehyde, respectively.By changing the content of water in the solvent system and comparing the changes of fluorescence signals, the results show that both L _ 3 and L _ 4 have AIE properties.In pure water system, L3 has a good ability to recognize Zn~(2. The fluorescence signal is enhanced. The detection limit is 4.51 脳 10 ~ (-5) M by 1:1 combination.At the same time, L4 has a good selectivity for Al~(3 in pure water system, which shows fluorescence enhancement. The binding mode is 1: 1, and the other ions have no interference with L4 to recognize Al~(3.The detection limit was 5.21 脳 10 ~ (-5) M.4.Schiff base L _ 5 and L _ 6 were prepared by the reaction of 2-aminobenzimidazole with 5-methylsalicylaldehyde and 5-bromosalicylaldehyde, respectively.Moreover, L5 has good ability to recognize zinc ion and emit strong fluorescence in ethanol solvent, while L6 can selectively recognize Mg~(2 ion in DMSO and bind it by 1:1.The detection limit was 3.49 脳 10 ~ (-5) M. 5. Schiff base L _ 7 and L _ 8 were synthesized by the reaction of 2-hydroxy-1-naphthalene formaldehyde and 2-oxo-4-aminophenyl) benzothiazole, respectively. The fluorescence changes of L7 and L8 in different water content systems were studied.It is found that both L7 and L8 have AIE properties.In DMSO, L7 can efficiently identify the trivalent ions, which can be combined in 1:1 mode, and the detection limit is 1.49 脳 10 ~ (-5) M(Al~(3 / L ~ (2.88 脳 10 ~ (-5)) M(Cr~(3 ~ (2. 12) 脳 10 ~ (-5) M(Fe~(3, and the detection limit is 1.49 脳 10 ~ (-5) M(Al~(3 / L ~ (-1) and 2.88 脳 10 ~ (-5) M(Cr~(3 / L ~ (-1) respectively.In the mixed system of DMSO and water, 1: 1 / L ~ (8) can effectively identify Cu~(2 ~ (2 +) by 1:1, and it is not affected by other ions, so it has good anti-interference ability, and the detection limit is 1.48 脳 10 ~ (-1) ~ (-6) M, and the detection limit is 1.48 脳 10 ~ (-1) ~ (-1) 路m ~ (-1) ~ (-1).
【學(xué)位授予單位】：渤海大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O657.3

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相關(guān)期刊論文 前3條

1 邊延江;王璐瓊;曹福祥;湯立軍;;兩種聚集熒光增強(qiáng)化合物的合成及性能研究[J];化學(xué)研究與應(yīng)用;2016年02期

2 Qianqian Li;Zhen Li;;AIE probes towards biomolecules: the improved selectivity with the aid of graphene oxide[J];Science China(Chemistry);2015年12期

3 邊延江;王璐瓊;溫馨;湯立軍;;三種席夫堿聚集熒光增強(qiáng)性質(zhì)及構(gòu)效關(guān)系的研究[J];化學(xué)研究與應(yīng)用;2014年12期

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