BODIPY衍生物與TPE冠醚主客體作用研究
發(fā)布時間:2018-05-05 16:14
本文選題:氟硼二吡咯 + 四苯乙烯 ; 參考:《南京理工大學》2017年碩士論文
【摘要】:超分子化學,它是一門涵蓋化學,生物學、材料學、物理學、信息科學等多學科交叉的學科。由超分子化學衍生出來很多相關學科,如超分子光學材料、超分子化學材料、超分子納米材料等。超分子化學可以用于,控制超分子納米粒子的聚集與分散,光電信號的處理、分子機械與器件的構造、刺激響應型超分子材料構建以及生理體內(nèi)藥物的運載和控釋等方面。本論文中,我們設計并合成了通過醚鍵將四苯乙烯(TPE)和二苯并-24-冠-8(DB24C8)連接在一起,構建一種對稱的具有聚集誘導發(fā)光性能的主體分子M1。同時我們設計并合成了以氟硼二吡咯(BODIPY)為母體結構的亞胺類BODIPY衍生物作為熒光客體分子M2。合成的所有分子都經(jīng)過1H-NMR,13C-NMR和MS等表征手段確定其結構。主體分子M1結構當中包含一個四苯乙烯結構,而具有該結構的化合物一般都有聚集誘導發(fā)光效應,兩個冠醚空穴為客體分子的進入創(chuàng)造了較大的可能性。客體分子M2具有BODIPY母體結構,而BODIPY類化合物在有機溶液中具有優(yōu)良的熒光性能。本文中客體分子M2帶有較長側鏈除了能夠更好的與冠醚空穴作用,另外一個性能是在水溶液中不會出現(xiàn)熒光猝滅效應。然后,我們研究了主體分子M1和客體分子M2在THF/H20= 1:9(V/V)的溶液中主客體相互作用行為。研究發(fā)現(xiàn)主體分子M1與客體分子M2之間存在熒光共振能量轉移現(xiàn)象,并且是從聚集誘導發(fā)光向非聚集誘導發(fā)光進行能量轉移。通過熒光滴定和核磁滴定實驗進一步確定了其主體分子M1與客體分子M2在中性,酸性和堿性條件下主客體作用的可能性,研究表明,該主客體系統(tǒng)的熒光共振能量轉移效率受酸堿度影響很小。該高pH穩(wěn)定性的熒光共振能量轉移體系的發(fā)現(xiàn)對于熒光分子開關、熒光探針、太陽能電池吸光材料的設計與開發(fā)具有十分重要意義。
[Abstract]:Supramolecular chemistry, it is a multidisciplinary subject covering chemistry, biology, materials science, physics, information science and so on. Many related subjects are derived from supramolecular chemistry, such as supramolecular optical materials, supramolecular chemical materials, supramolecular nanomaterials and so on. Supramolecular chemistry can be used to control the aggregation and dispersion of supramolecular nanoparticles, the processing of photoelectric signals, the construction of molecular machinery and devices, the construction of stimulative supramolecular materials and the delivery and controlled release of drugs in vivo. In this thesis, we have designed and synthesized a symmetric host molecule M1 with aggregation induced luminescence by binding tetrastyrene (TPE) with dibenzo-24-crown-8 (DB24C8) by ether bond. At the same time, we have designed and synthesized imines BODIPY derivatives with fluoroborate dipyrrolidine (BODIPY) as the fluorescent guest molecule M2. All the synthesized molecules were characterized by 1H-NMR-13C-NMR and Ms. The structure of the host molecule M1 contains a tetrastyrene structure, and the compounds with this structure generally have aggregation induced luminescence effect. Two crown ether holes create a great possibility for the entry of the guest molecule. The guest molecule M2 has the BODIPY matrix structure, while the BODIPY class compounds have excellent fluorescence properties in organic solution. In this paper, the guest molecule M2 has a long side chain which can interact with crown ether hole better, and another property is that there is no fluorescence quenching effect in aqueous solution. Then, we study the host-guest interaction between host molecule M1 and guest molecule M2 in THF / H20 = 1: 9 V / V) solution. It is found that there is a phenomenon of fluorescence resonance energy transfer between host molecule M1 and guest molecule M2, and the energy transfer is from agglomeration induced luminescence to nonaggregation induced luminescence. The possibility of host and guest interaction between host molecule M1 and guest molecule M2 in neutral, acidic and alkaline conditions was further determined by fluorescence titration and nuclear magnetic titration. The fluorescence resonance energy transfer efficiency of the host and guest system is very little affected by pH. The discovery of the fluorescence resonance energy transfer system with high pH stability is of great significance for the design and development of fluorescent molecular switches, fluorescent probes and absorbent materials for solar cells.
【學位授予單位】:南京理工大學
【學位級別】:碩士
【學位授予年份】:2017
【分類號】:O641.3
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