以蒽为中心的有机共轭小分子的设计合成及其光学性质的研究

发布时间：2018-03-14 16:08

本文选题：蒽　切入点：压致荧光变色　出处：《青岛科技大学》2017年硕士论文　论文类型：学位论文

【摘要】：近些年,共轭有机小分子材料备受瞩目。它具有来源广泛、结构简单、易于纯化以及颜色饱和度高等特点,因此在光电领域具有广泛的应用。目前主要应用于记忆存储、有机电致发光器件(OLED)、有机光伏电池及化学传感器等方面。由于蒽与普通的芳环及芳杂环的电子结构不同,它的刚性大平面形成了一个大的共轭体系,具有高荧光性和高热稳定性,且蒽的2,6,9,10位可以键接上不同的功能基团,所以我们课题组一直致力于研究以蒽为中心的有机光电材料。本文就是以蒽为中心设计并合成了七个烷基链长度不同(C1-C7)的9,10-(二烷基氨基苯乙烯基)蒽衍生物(9,10-DSA)和4-(蒽-9-苯基菲并咪唑)苯胺(PTPAN)及4-(蒽-9-苯基恶二唑)苯胺(OTPAN),并研究了它们的光学性质,主要内容如下:1.我们将蒽的9,10位通过双键键接上不同长度的烷基链(C1-C7),得到一系列9,10-二苯乙烯基蒽衍生物(9,10-DSA),经过研究发现,烷基链长度会影响其光学性质。在固态下,通过对该系列化合物施加不同的作用力(剪切力/压应力、热回复、再剪切/再碾压、熏蒸),我们发现该系列化合物的位移大小与作用力及烷基链长度有明显的关系,并且这些现象是重复可逆的。这也就证明了我们合成的这一系列衍生物具有压致荧光变色(PFC)特性。2.我们设计合成了D-A-D结构的两个分子PTPAN、OTPAN,经过测试研究发现,这两个化合物均有溶剂化效应,从整体来看,最大荧光发射波长随着溶剂极性的增强而逐渐红移(分别红移95 nm、74 nm)且峰形逐渐变宽。PTPAN和OTPAN两种材料在不同溶剂中的荧光量子效率随溶剂极性的增大而降低,在乙腈中分别为0.220、0.251,在正己烷中分别为0.732、0.761。从热稳定性以及电化学数据来看,PTPAN优于OTPAN,是一种非常具有潜力的深蓝色荧光器件。
[Abstract]:In recent years, conjugated organic small molecular materials have attracted much attention. They are widely used in the field of optoelectronics, such as wide source, simple structure, easy purification and high color saturation. At present, they are mainly used in memory storage. Organic electroluminescent devices, organic photovoltaic cells and chemical sensors. Because anthracene has different electronic structures from ordinary aromatic and heterocyclic rings, its rigid large plane forms a large conjugate system. It has high fluorescence property and high thermal stability, and can bond with different functional groups at 2 ~ 6 ~ 9 ~ 9 ~ 10 position of anthracene. Therefore, our research group has been devoted to the study of anthracene centered organic optoelectronic materials. In this paper, we have designed and synthesized seven alkyl chain derivatives (9 (dialkylamino phenylethyl) anthracene) with different alkyl chain length (C _ 1-C _ 7). The optical properties of 4 (anthracene 9 phenanthroline imidazole) aniline (PTPAN) and 4 (anthracene 9 phenyl oxadiazole) aniline (OTPAN) were studied. The main contents are as follows: 1.The alkyl chain (C _ 1-C _ 7N) with different lengths is bonded to the 9 / 10 position of anthracene by double bonding to obtain a series of 9 ~ (10) -diphenylvinyl anthracene derivative (9 ~ (10)) -DSAN. It is found that the length of alkyl chain will affect the optical properties of anthracene, and the alkyl chain length will affect the optical properties of anthracene in solid state. By applying different forces (shear force / compressive stress, thermal recovery, reshear / rerolling, fumigation) to the series of compounds, we found that the displacement of the series compounds is obviously related to the action force and the length of alkyl chain. And these phenomena are repetitive and reversible, which proves that the series of derivatives we synthesized have the properties of pressure induced fluorescence discoloration (PFC). 2. We have designed and synthesized two molecules of D-A-D structure, PTPAN- OTPAN, and we have found that the two molecules of D-A-D structure are PTPAN- OTPAN. Both of these compounds have solvation effects, and as a whole, The maximum fluorescence emission wavelength gradually shifted red with the increase of solvent polarity (95 nm ~ 74 nm respectively) and the peak shape gradually widened. The fluorescence quantum efficiency of two kinds of materials, PTPAN and OTPAN, decreased with the increase of solvent polarity. In acetonitrile and n-hexane, 0.220 and 0.251, respectively. PTPAN is superior to OTPAN in thermal stability and electrochemical data, so it is a promising dark blue fluorescence device.
【学位授予单位】：青岛科技大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.3

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