【摘要】：由于具有出色的光致變色性質(zhì)、熱穩(wěn)定性和抗疲勞性,二芳烯最初在高密度信息存儲(chǔ)方面的潛在應(yīng)用引起了人們廣泛關(guān)注。近年來,基于二芳烯的多重調(diào)控?zé)晒忾_關(guān)和光化學(xué)傳感引起了人們的廣泛關(guān)注,這些新的功能將進(jìn)一步推動(dòng)二芳烯化合物的發(fā)展,對(duì)二芳烯的未來格局及應(yīng)用帶來全新的改變。目前,將二芳烯化合物作為光化學(xué)傳感器已經(jīng)成為一個(gè)新的研究熱點(diǎn),因此,設(shè)計(jì)合成新的對(duì)金屬離子有獨(dú)特響應(yīng)的二芳烯正受到了廣泛的關(guān)注。本論文通過分子設(shè)計(jì)、合成,將金屬離子識(shí)別基團(tuán)引入到含羥基的二芳烯分子中,構(gòu)建了具有多重調(diào)控以及離子識(shí)別性能的二芳烯衍生物。著重研究了這些二芳烯的多重調(diào)控性能和對(duì)金屬離子的光化學(xué)傳感性能,包括多重調(diào)控的熒光開關(guān)、金屬離子的熒光和比色傳感器以及分子邏輯電路的構(gòu)建等。具體研究內(nèi)容和研究成果如下:第1章綜述了光化學(xué)傳感器的研究進(jìn)展。結(jié)合二芳烯化合物的研究現(xiàn)狀,綜述了基于二芳烯的離子傳感器的研究進(jìn)展,提出研究課題。第2章設(shè)計(jì)合成了一種末端含水楊醛基團(tuán)的二芳烯化合物。系統(tǒng)研究了其在光和酸/堿作用下的多重相應(yīng)的光致變色性質(zhì)。研究結(jié)果顯示,該化合物具有優(yōu)異的光致變色性質(zhì)。去質(zhì)子化后,閉環(huán)態(tài)的最大吸收波長紅移了100 nm,熒光調(diào)制效率從30%提高到55%。第3章設(shè)計(jì)合成了一種不對(duì)稱的含雙-2-甲基吡啶胺的二芳烯化合物。系統(tǒng)地研究了其光致變色性質(zhì)以及其與Zn~(2+)的相互作用。研究結(jié)果顯示,該化合物在溶液和晶相中均表現(xiàn)出優(yōu)異的光致變色性質(zhì)。與Zn~(2+)的相互作用后,其熒光強(qiáng)度增強(qiáng)了2倍,并伴隨著熒光的顏色從黑色變成了亮藍(lán)色。證明了該化合物可以作為Zn~(2+)的熒光增強(qiáng)傳感器。第4章利用Mannich反應(yīng),將雙-2-甲基吡啶胺引入到末端含苯酚的二芳烯分子中。系統(tǒng)地研究了該化合物的光致變色性質(zhì)以及與金屬離子的相互作用。研究結(jié)果顯示,其閉環(huán)態(tài)與Cu~(2+)作用后,其最大吸收波長從558 nm藍(lán)移到504nm,吸收強(qiáng)度增加了3.3倍,并伴隨著溶液的顏色從紫色到紅色的顯著變化。通過滴定實(shí)驗(yàn)數(shù)據(jù)分析,該化合物可以作為Cu~(2+)的比色傳感器。第5章通過席夫堿單元,將二芳烯和8-氨基喹啉單元進(jìn)行連接,合成了一個(gè)新的二芳烯化合物。系統(tǒng)地研究了該化合物在光和化學(xué)試劑作用下的多重調(diào)控性質(zhì)。實(shí)驗(yàn)結(jié)果顯示,該化合物對(duì)Mg~(2+)和Ca~(2+)具有較高的選擇性和靈敏性,并表現(xiàn)出不同的熒光發(fā)射和顏色變化。證明了該化合物可以作為Mg~(2+)和Ca~(2+)的熒光/比色雙通道傳感器。此外,基于其多重調(diào)控性質(zhì),可以構(gòu)建一個(gè)單分子的組合邏輯電路。第6章結(jié)論與展望
[Abstract]:Due to their excellent photochromic properties, thermal stability and fatigue resistance, the potential applications of diarylenes in high density information storage have attracted much attention. In recent years, the multilevel control fluorescence switch and photochemical sensing based on diarylene have attracted wide attention. These new functions will further promote the development of diarylene compounds and bring new changes to the future pattern and application of diarylerene. At present, diarylene compounds as photochemical sensors have become a new research hotspot. Therefore, the design and synthesis of new diarylerenes which have unique response to metal ions have been paid more and more attention. Through molecular design and synthesis, the metal ion recognition group was introduced into diarylerenes containing hydroxyl groups, and the diaryene derivatives with multiple regulation and ion recognition properties were constructed. The properties of these diarylenes in multiplex regulation and photochemical sensing of metal ions are mainly studied, including multiplex fluorescent switches, fluorescence and colorimetric sensors of metal ions, and the construction of molecular logic circuits, etc. The research contents and results are as follows: chapter 1 summarizes the research progress of photochemical sensors. In this paper, the research progress of diarylene-based ion sensors is reviewed, and the research topics are put forward. In chapter 2, a kind of diarylerene with water-terminated salicylidene group was designed and synthesized. The photochromic properties of the photochromic agents under the action of acid / alkali are systematically studied. The results show that the compound has excellent photochromic properties. After deprotonation, the maximum absorption wavelength of the closed-loop state is redshifted from 30% to 55%, and the fluorescence modulation efficiency of 100 nm, is increased. In chapter 3, an asymmetric diarylene compound containing bis-2-methylpyridine was designed and synthesized. The photochromism and its interaction with Zn~ (2) were studied systematically. The results show that the compound exhibits excellent photochromic properties in both solution and crystalline phase. After interaction with Zn~ (2), the fluorescence intensity increased by 2 times, and the color of fluorescence changed from black to bright blue. It is proved that the compound can be used as a fluorescence enhanced sensor for Zn~ (2). In chapter 4, Mannich reaction was used to introduce bis-2-methylpyridine into the diarylenes containing phenol at the end. The photochromic properties of the compound and its interaction with metal ions were systematically studied. The results show that the maximum absorption wavelength shifts from 558 nm blue to 504 nm after the interaction of the closed-loop state with Cu~ (2), and the absorption intensity increases by 3.3 times, and the color of the solution changes significantly from purple to red. The compound can be used as a colorimetric sensor for Cu~ (2) by analyzing the titration data. In chapter 5, a new diaryene compound was synthesized by connecting diarene with 8-aminoquinoline unit by Schiff base unit. The multiple regulation properties of the compound under the action of light and chemical reagents were systematically studied. The experimental results show that the compound has high selectivity and sensitivity to Mg~ (2) and Ca~ (2), and shows different fluorescence emission and color change. It is proved that the compound can be used as Mg~ (2) and Ca~ (2) fluorescence / colorimetric dual channel sensors. In addition, a single molecular combinatorial logic circuit can be constructed based on its multiple modulation properties. Chapter 6 conclusion and Prospect
【學(xué)位授予單位】：南昌大學(xué)
【學(xué)位級(jí)別】：博士
【學(xué)位授予年份】：2016
【分類號(hào)】：TP212.2

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