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以苝四酸酐为原料合成了1,7-二溴-3,4,9,10-苝四酸酐(PeryBr2)、N,N′-二(十二烷基)-1,7-二溴-3,4,9,10-苝四羧酸二酰亚胺(DD-PeryBr2)和N,N′-二(十二烷基)-1,7-二对叔丁基苯氧基-3,4,9,10-苝四羧酸二酰亚胺(DD-PeryBp2) 3种苝四羧酸二酰亚胺类化合物,并对其结构和性能利用紫外-可见吸收光谱、傅立叶红外光谱、核磁共振、质谱、热分析和荧光光谱测试技术进行了表征和测试。 结果表明,DD-PeryBp2能很好的溶于甲苯、氯仿、四氢呋喃等常用有机溶剂。 紫外可见最大吸收波长和荧光最大发射波长分别为548和576 nm。 DD-PeryBp2具有很好的热稳定性,质量损失5%时的温度为433 ℃。 相似文献
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制备了两类酰胺位置含有吸电子基团的苝酰亚胺衍生物N,N′-双(三氟乙基)-1,7-二溴-3,4,9,10-苝二酰亚胺(PTCDI-3F)和N,N′-双(七氟丁基)-1,7-二溴-3,4,9,10-苝二酰亚胺(PTCDI-7F),并测定了其气敏传感性能.结果表明,两类苝酰亚胺衍生物在水合肼气氛中(10ppm)的灵敏度变化值基本相同、电阻均降低约4个数量级.其原因在于两者具有相同的最低空轨道能级.这表明酰胺位取代基对苝酰亚胺衍生物气敏传感性能的影响较小. 相似文献
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应用密度泛函理论研究了四种二萘嵌苯二酰亚胺(PDI)(N,N'-二萘嵌苯-3,4,9,10-四羧酸二酰亚胺(1), N,N'-二(3-氯苯甲基)二萘嵌苯-3,4,9,10-四羧酸二酰亚胺(2), N,N'-二(3-氟苯甲基)二萘嵌苯-3,4,9,10-四羧酸二酰亚胺(3)和N,N'-二(3,3-二氟苯甲基)二萘嵌苯-3,4,9,10-四羧酸二酰亚胺(4))半导体材料的最高占据轨道和最低未占据轨道能量、离子化能和电子亲和能以及在电荷传导过程中的重组能. 与化合物2-4的最高占据轨道和最低未占据轨道能量变化相同, 在PDI分子外围引入氯苯甲基或氟苯甲基后导致化合物2-4的绝热电子亲和能有不同程度的增加. 应用Marcus电子传导理论, 计算了这四种半导体材料应用于有机场效应晶体管在电子传递过程中的电子耦合和迁移率. 计算结果表明:这四种化合物相对于金属金电极而言具有较小的电子注入势垒, 是优良的n型半导体材料. 计算的这四种半导体材料的电子传输迁移率分别为5.39, 0.59, 0.023和0.17 cm2·V-1·s-1. 通过研究化合物分子在还原过程中几何结构变化和在化合物3晶体中不同类型的电子传递路径, 合理地解释了化合物1-4在有机场效应晶体管电荷迁移过程中具有较高的电子迁移率. 相似文献
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本文以3,4,9,10-苝四羧酸酐为原料合成了3,4,9,10-苝四羧酸和N,N′-二((3-二甲氨基)丙基)-3,4,9,10-苝二酰亚胺,这两个苝系衍生物在水溶液中的溶解度和荧光效率并不高,但是在不同的pH值条件下,两个衍生物形成了水溶性较强的PTCA阴离子和PMI阳离子,并且具有不同的荧光性质。实验结果显示:PTCA在pH 10.0的碱性环境中显示出较强的蓝色荧光,PMI在pH 5.0的弱酸性环境中显示出较强的黄色荧光,并且根据测试的荧光光谱推测了两种具有相同发色团、相似结构的衍生物在不同pH环境中可能存在分子或离子的堆积模式及发光模式。本文还探讨了PTCA阳离子在pH 6.0缓冲溶液中,作为离子型荧光探针对部分金属离子的识别。 相似文献
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合成了三种新型的有机电子受体: N,N'-二(2-氟代苯基)-3,4,9,10-苝四羧基二酰亚胺(D2MFPP)、N,N'-二(3-氟代苯基)-3,4,9,10-苝四羧基二酰亚胺(D3MFPP)和N,N'-二(4-氟代苯基)-3,4,9,10-苝四羧基二酰亚胺(D4MFPP). 利用元素分析、傅立叶变换红外(FTIR)等方法表征了它们的分子结构, 用紫外-可见光吸收光谱(UV-Vis)、X射线衍射(XRD)和原子力显微镜(AFM)等手段研究了氟代位置对苝酰亚胺薄膜聚集态结构的影响, 发现氟代使苝酰亚胺的聚集态发生变化, 且不同位置的氟代对其影响也不一样. 除了分子结构的影响, 外场条件也会产生很大的作用. 通过制备场效应晶体管研究了其电子传输性能, 发现氟代后器件的空气稳定性有明显提高. 相似文献
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不同氟取代基对苝酰亚胺电子迁移率的影响 总被引:1,自引:0,他引:1
利用空间电荷限制电流(SCLC)法测试了二种氟代苝酰亚胺的电子迁移率, 一种是N,N'-二(五氟代苯基)-3,4,9,10-苝四羧基二酰亚胺(1), 另一种是N,N'-二(1,1-二氢十五氟代辛基)-3,4,9,10-苝四羧基二酰亚胺(2). 结果发现, 化合物2的电子迁移率要比1高1~2个数量级. UV-Vis, XRD, SEM和AFM等表征手段证明, 这一现象可以用不同的氟取代基导致不同的聚集态结构来解释: 对于化合物1而言, 苯环平面与苝环平面之间存在大的夹角, 破坏了苝酰亚胺分子的平面性, 再加上刚性的氟代苯环大的空间位阻作用, 化合物1分子无法依靠相邻苝环之间的重叠排列而结晶, 只能无序堆积形成非晶膜; 与之相反, 在化合物2分子中苝环上的端基是柔性的锯齿状氟代烷基链, 空间位阻小, 化合物2分子能通过相邻苝环之间相互接近而形成的π-π偶合作用而结晶, 因此有利于电子在苝酰亚胺分子间的跳跃传输. 相似文献
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Designed and synthesized a new highly water soluble N,N1-bis(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)-perylene -3,4,9,10-tetracarboxylic diimide from 2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethanamine and perylene-3,4,9,10- tetracarboxylic dianhydride.The compound was characterized by 1H,13C,2D NMR,mass and IR techniques.The compound is highly fluorescent with good solubility in water and other polar solvents. 相似文献
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Silly F Shaw AQ Castell MR Briggs GA 《Chemical communications (Cambridge, England)》2008,(16):1907-1909
The mixing of perylene-3,4,9,10-tetracarboxylic diimide (PTCDI) and 1,3,5-triazine-2,4,6-triamine (melamine) at room temperature in a ratio of 3 : 4 on Au(111) leads to the formation of a new chiral "pinwheel" structure. 相似文献
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Kouhei Watanabe Ayano Taniguchi Daiki Kaji Nobuyuki Hara Tomomasa Hosoya Aoba Kanesaka Takunori Harada Hiroyuki Nishikawa Yoshitane Imai 《Tetrahedron》2019,75(21):2944-2948
Organic fluorescent molecules are gaining importance because of their potential applications in many devices. Optically active N,N′-bis((1R)-1-naphthylethyl)perylene-3,4,9,10-tetracarboxylic diimide [(R,R)-1-BNP] and N,N′-bis((1R)-2-naphthylethyl)perylene-3,4,9,10-tetracarboxylic diimide [(R,R)-2-BNP] and their antipode, [(S,S)-1-BNP and (S,S)-2-BNP], emit aggregation-induced enhanced (AIEnh) circularly polarized luminescence (CPL) on both a solid organic polymer film (poly(methyl methacrylate)) and solid inorganic KBr pellet. An opposite chirality is essential for generating CPL of inverted sign. However, a pair of enantiomeric organic molecules may not always be easy to prepare. Interestingly, the chiral perylene fluorophores synthesized in this study can emit both positive and negative AIEnh-CPL in the solid state, depending on their position on the naphthylene groups. In addition, no CPL was observed in these compounds from their dilute solutions. 相似文献
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苝四羧酸二酰亚胺系有机光导材料的光敏性与结构的关系研究 总被引:2,自引:0,他引:2
用AM1和CNDO方法优化得PTCAs可能存在的稳定结构.对比晶体结构发现化合物3-5晶体中以成键能较高的共面结构存在,该结构有利于形成分子的紧密堆积.最小二乘法拟合结果表明单取代化合物的光敏性与分子激发跃迁能(△EL-H)存在定量构效关系(QSPR),r>0.95;双取代化合物的光敏性与从CGL到CTL的空穴注入效率(△ET-G)存在QSPR,r>0.97.表明光电转换两个过程在不同类型PTCAs的光敏性产生过程中占据的作用不同:分子激发难易是影响单取代化合物光敏性的主要因素;而空穴注入效率是影响双取代化合物光敏性的主要因素. 相似文献
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V. V. Semenov N. V. Zolotareva E. Yu. Ladilina S. A. Lermontova L. G. Klapshina I. S. Grigor’ev M. A. Lopatin A. I. Kirillov T. I. Kulikova G. A. Domrachev 《Russian Journal of General Chemistry》2011,81(7):1496-1506
The reaction of perylene-3,4,9,10-tetracarboxylic acid dianhydride with 3-aminopropyltriethoxysilane and hexamethyldisilazane
was investigated. A possibility of obtaining a new dye resistant to UV light and heating (up to 300°C), consisting of structural
fragments of perylene-3,4,9,10-tetracarboxydiimede, diethoxysiloxane, and 3-aminopropylethoxysiloxane was demonstrated. A
compound obtained in 43% yield by heating (7 h, 180–200°C) perylene-3,4,9,10-tetracarboxylic acid dianhydride with excess
3-aminopropyltriethoxysilane in the presence of catalytic amounts of zinc acetate is an oligomer appropriate for the solgel
process, displays strong luminescence in the red spectral region (540–620 nm), and has good film-forming properties. The participation
of hexamethyldisilazane consists in binding water molecules formed in the reaction of perylene-3,4,9,10-tetracarboxylic acid
dianhydride with 3-aminopropyltriethoxysilane and in the formation of trimethylsilanol which replaces a part of the EtO groups
at the silicon atoms by a more bulky Me3SiO groups, causing significant increase in the solubility of the dye in organic solvents and silicon sol-gel monomers. The
hydrolysis of silicon-containing dye and subsequent dehydration of the resulting gel lead to the formation of insoluble xerogel. 相似文献
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Tam-Chang SW Iverson IK Helbley J 《Langmuir : the ACS journal of surfaces and colloids》2004,20(2):342-347
The chromonic liquid-crystalline properties of bis-(N,N-diethylaminoethyl)perylene-3,4,9,10-tetracarboxylic diimide dihydrochloride in an aqueous solution were investigated by polarized light microscopy and 2H NMR spectroscopy. Both techniques indicate a narrow I + N biphasic region and a broad N phase region at concentrations ranging from approximately 6.9 to approximately 30 wt % at room temperature. Optical microscopy indicates that a hexagonal M phase exists at higher concentrations. The variation of the I --> N + I and N + I --> N transition temperatures with concentration was studied by 2H NMR spectroscopy. Finally, the effects of temperature and concentration on the order parameter of the N phase were investigated by 2H NMR using a tetra-deuterated derivative. A value of 0.97 was obtained for the N phase at its upper concentration limit. 相似文献
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Nucleophilic substitution of N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxydiimide (PTCDI) with an excess of corresponding alkanol in the presence of sodium hydride or anhydrous potassium carbonate at 85-100 degrees C provided both di(alkoxy)- and mono(alkoxy)-substituted PTCDI compounds, namely, N,N'-dicyclohexyl-1,7-di(alkoxy)perylene-3,4:9,10-tetracarboxydiimide (3) and N,N'-dicyclohexyl-1-bromo-7-alkoxyperylene-3,4:9,10-tetracarboxydiimide (2). Starting from mono(alkoxy)-substituted PTCDI, nucleophilic substitution with thiol, thiophenol, or alkylamine led to the formation of unsymmetrical 1,7-di(substituted) PTCDI compounds (7-10). For the purpose of comparative studies, symmetrical di(substituted) N,N'-dicyclohexyl-1,7-di(alkylthio)perylene-3,4:9,10-tetracarboxydiimide (4), N,N'-dicyclohexyl-1,7-di(thiophenyl)perylene-3,4:9,10-tetracarboxydiimide (5), and N,N'-dicyclohexyl-1,7-di(alkylamine)perylene-3,4:9,10-tetracarboxydiimide (6) have also been prepared by a similar nucleophilic substitution. These newly prepared PTCDI compounds have been characterized by a wide range of spectroscopic methods in addition to elemental analysis. Electronic absorption and fluorescence studies revealed that the absorption and emission bands as well as the fluorescence quantum yield can be tuned continuously over a large range by incorporating substituents with different electron-donating abilities. 相似文献