本文關(guān)鍵詞： 三芳基硼 雙功能熒光探針 汞離子 氟離子 pH　出處：《山東大學(xué)》2016年碩士論文　論文類型：學(xué)位論文

【摘要】：Hg2+作為毒性最大的重金屬離子之一,對(duì)環(huán)境以及人體健康造成了極大的危害；F-以氟化物的形式廣泛分布在自然界中,對(duì)生態(tài)環(huán)境以及人體健康起著重要的作用；此外,pH作為人體健康的重要指標(biāo)之一,在細(xì)胞的各種代謝過(guò)程中起著重要的作用。為此,建立有效的檢測(cè)Hg2+、F-以及pH的方法具有重要的意義。相比于傳統(tǒng)的分析方法,如原子吸收光譜法、高效液相色譜法、電化學(xué)分析法等,熒光檢測(cè)具有高靈敏度、高選擇性和簡(jiǎn)單方便等優(yōu)點(diǎn),受到越來(lái)越多的關(guān)注。雖然目前已報(bào)道了很多檢測(cè)Hg2+、F-和pH的熒光探針?lè)肿?但能夠同時(shí)檢測(cè)兩種物質(zhì)的雙功能化熒光探針還非常有限。在最近的研究中,我們課題組設(shè)計(jì)合成了一種基于三芳基硼的F-比率熒光探針BN,2-二米基硼基-2'-(N,N-二甲氨基)聯(lián)苯,三芳基硼中心和F-的絡(luò)合可以引起熒光大幅度的藍(lán)移(165 nnm),進(jìn)而可以實(shí)現(xiàn)對(duì)F-的比率熒光檢測(cè)。值得注意的是,BN的氨基對(duì)位親電取代活性較高,為此我們希望通過(guò)在此位置引入可以檢測(cè)其他離子的官能團(tuán)以實(shí)現(xiàn)對(duì)氟離子和其他離子的同時(shí)檢測(cè)�；谶@一設(shè)計(jì)思想,我們開(kāi)展了一下兩方面的工作：首先,我們通過(guò)甲�；肴┗�,再與硫醇縮合,在BN氨基的對(duì)位引入了對(duì)Hg2+有響應(yīng)的硫縮醛,合成了化合物BN-S,作為同時(shí)檢測(cè)Hg2+和F-的雙功能化比率熒光探針。BN-S中存在著分子內(nèi)電荷轉(zhuǎn)移,不僅在有機(jī)相中會(huì)發(fā)射強(qiáng)的熒光,而且即使在水相中形成納米聚集體的狀態(tài)下熒光也很強(qiáng)。Hg2+的加入可以誘導(dǎo)硫縮醛發(fā)生脫保護(hù)反應(yīng)生成醛基,使體系的最大發(fā)射波長(zhǎng)發(fā)生藍(lán)移,顏色由黃綠色變?yōu)榫G色。而氟離子的加入,打斷了體系中的pπ-π*共軛,可以使體系熒光發(fā)生大幅度的藍(lán)移,熒光顏色由黃色變?yōu)樗{(lán)色。因此BN-S可以作為同時(shí)檢測(cè)Hg2+和F-的雙功能化比率熒光探針,此外,BN-S對(duì)Hg2+的檢測(cè)可以以納米聚集體形式在水相中進(jìn)行。其次,我們又通過(guò)溴代反應(yīng)及Suzuki偶聯(lián)反應(yīng),在BN的氨基對(duì)位引入了對(duì)H+有響應(yīng)的吡啶環(huán),合成了熒光分子1,2,3,以實(shí)現(xiàn)同時(shí)對(duì)氟離子和pH的熒光檢測(cè)。這些研究結(jié)果為深入研究BN的光學(xué)性質(zhì),以它為基本單元進(jìn)行官能團(tuán)修飾設(shè)計(jì)合成各種不同的雙功能化熒光探針提供了一定的理論依據(jù)。
[Abstract]:One of the most toxic heavy metal ions as Hg2+, caused great harm to the environment and human health; F- in the form of fluoride is widely distributed in nature, on the ecological environment and human health plays an important role; in addition, pH as important health indicator, it plays an important role in various metabolic processes cells. Therefore, the establishment of effective detection of Hg2+, the significance of F- and pH analysis method. Compared with traditional methods, such as atomic absorption spectrometry, high performance liquid chromatography, electrochemical analysis, fluorescence detection with high sensitivity, high selectivity and advantages such as simple and convenient, more and more concern. Although there has been reported a lot of detection of Hg2+, F- and pH fluorescent probe molecules, but also can detect double function of two kinds of material of the fluorescent probe is very limited. In a recent study In our group, we designed and synthesized a three arylboron F- ratio fluorescent probe based on BN, 2- two -2'- (N, Mickey boron based N- two dimethylamino biphenyl), complex three arylboron center and F- can cause large amplitude fluorescence blue shift (165 NNM), which can be achieved on the the F- ratio of fluorescence detection. It is worth noting that the amino BN para electrophilic substitution of higher activity, so we hope that through the introduction of functional groups in this position can detect other ions to achieve the detection of fluoride ion and other ions at the same time. This design based on the idea, we carried out two aspects: first of all, we introduce the formyl aldehyde with thiol condensation in Para BN amino thioacetals are introduced on the responses of Hg2+, compound BN-S, at the same time as the dual function of detection of Hg2+ and F- ratio of fluorescence probe.BN-S exists in intramolecular charge transfer Shift, not only in the organic phase will emit strong fluorescence, and the formation of nano aggregates even in aqueous solution under the condition of fluorescence is also very strong with the addition of.Hg2+ can occur deprotection reaction of aldehyde acetal induced by sulfur, the maximum emission wavelength of the blue shift system, color from yellow green color is green. The fluoride added P, interrupted pi conjugation in the system, can make the fluorescence system has the large scale blue shift, fluorescent color from yellow to blue. So BN-S can be used as a dual function of detection of Hg2+ and F- at the same time, the ratio of fluorescence probe, in addition, the detection of Hg2+ BN-S can be carried out in the form of nano aggregates in aqueous phase. Secondly, we through bromination reaction and Suzuki coupling reaction, the amino para BN introduced a pyridine ring on the response of the H+, the synthesis of fluorescent molecules 1,2,3, to achieve simultaneous fluorescent detection of fluoride ion and pH test. These research The results provide a theoretical basis for in-depth study of the optical properties of BN and the design and synthesis of various bifunctional fluorescent probes based on its basic unit functionalization.

【學(xué)位授予單位】：山東大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2016
【分類號(hào)】：O657.3

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本文編號(hào)：1450617