N-cyclohexyl-1,7-bis(pyrrolidin-1-yl)-perylene-3,4-imide-9,10-anhydride | 404871-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-cyclohexyl-1,7-bis(pyrrolidin-1-yl)-perylene-3,4-imide-9,10-anhydride
• 英文别名: 18-Cyclohexyl-11,22-dipyrrolidin-1-yl-7-oxa-18-azaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 404871-18-7
• 化学式: C₃₈H₃₃N₃O₅
• 分子量: 611.697
• InChiKey: FEMBNUNZKLEUKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  46
• 可旋转键数：
  3
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-1,7-bis(pyrrolidin-1-yl)-perylene-3,4-imide-9,10-anhydride 在 氢氧化钾 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以61%的产率得到1,7-dipyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisanhydride
  参考文献：
  名称：

  Ultrafast Photoinduced Charge Separation Resulting from Self-assembly of a Green Perylene-based Dye into π-Stacked Arrays

  摘要：

  Condensation of 3,4.5-tris(n-dodecyloxy)aniline with the green chromophore 1,7-bis(N-pyrrolidinyl)perylene-3,4,9, 10-tetracarboxylic dianhydride yields N,N'-bis(3,4,5-tris(n-dodecyloxy)phenyl)-1,7-bis(N-pyrrolidinyl)perylene-3,4;9,10-bis(dicarboximide), 5PDI-TAP, which absorbs light strongly from 550 to 750 rim. 5PDI-TAP dissolves readily in methylcyclohexane (MCH), resulting in self-assembly into H-aggregates. Small-angle X-ray scattering data obtained on 10(-4) M solutions of 5PDI-TAP in MCH show that the aggregates are pi-stacked monodisperse pentamers. Femtosecond transient absorption spectroscopy on solutions of (5PDI-TAP)(5) in MCH shows evidence of charge separation occurring with tau less than or equal to 150 fs, between adjacent stacked members of 5PDI-TAP within the pentamer followed by charge recombination with tau = 860 ps. Transmission electron microscopy of 5PDI-TAP films cast from solution show isolated bundles of columnar aggregates. (5PDI-TAP)(n) is a potentially useful material for organic photovoltaics because efficient photoinduced charge veneration is an intrinsic property of the assembly.

  DOI：

  10.1021/jp044796q
• 作为产物：
  描述：

  N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxylic dianhydride 在 氢氧化钾 作用下， 以 水 、 异丙醇 为溶剂， 反应 26.75h， 生成 N-cyclohexyl-1,7-bis(pyrrolidin-1-yl)-perylene-3,4-imide-9,10-anhydride
  参考文献：
  名称：

  Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

  摘要：

  A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylenE! bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N'-Dicyclohexyl- 1,7-dibromoperylene bisimide 1, 7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure l,'7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a-c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.

  DOI：

  10.1021/jo048880d

文献信息

• Energy Transfer in Calixarene-Based Cofacial-Positioned Perylene Bisimide Arrays
  作者：Catharina Hippius、Felix Schlosser、Myroslav O. Vysotsky、Volker Böhmer、Frank Würthner

  DOI：10.1021/ja058007+

  日期：2006.3.1

  steady state and time-resolved fluorescence spectroscopy. Upon excitation of the inner orange dye at 490 nm of array 3, strong fluorescence emission of the outer green perylene bisimide (PBI) chromophore at 744 nm is observed. The fluorescence excitation spectra of compounds 3 and 4 (lambdadet = 850 nm) show all absorption bands of the parent chromophores (e.g., all perylene units contribute to the emission

  多发色苝双酰亚胺-杯[4]芳烃阵列的合成具有多达五个苝单元（包含橙色、紫色和绿色苝双酰亚胺发色团）和单发色模型化合物的合成是通过随后对单 Boc 功能化杯[4]进行酰亚胺化来实现的具有三种不同类型的苝双酰亚胺染料单元的芳烃接头。用紫外/可见光吸收和稳态和时间分辨荧光光谱研究了所有化合物的光学性质。在阵列 3 的 490 nm 处激发内部橙色染料后，观察到外部绿色苝双酰亚胺 (PBI) 生色团在 744 nm 处发出强荧光。化合物 3 和 4（λdet = 850 nm）的荧光激发光谱显示了母体发色团的所有吸收带（例如，所有苝单元都有助于绿色 PBI 的 S1 状态的发射）。因此，在不存在（tauD = 5.1 ns）和存在受体（tauDA = 0.8 ns）的情况下，荧光发射和激发光谱以及荧光寿命的时间分辨数据表明苝双酰亚胺染料之间的有效能量转移过程单位。对于双发色阵列 4，计算出的能量转移率为
• Excited-State Symmetry Breaking in Cofacial and Linear Dimers of a Green Perylenediimide Chlorophyll Analogue Leading to Ultrafast Charge Separation
  作者：Jovan M. Giaimo、Alexey V. Gusev、Michael R. Wasielewski

  DOI：10.1021/ja026422l

  日期：2002.7.1

  intradimer electron transfer occurs in cof-5PDI2 in toluene with tau = 0.17 ps followed by charge recombination to the ground state with tau = 222 ps. Similar measurements on lin-5PDI2 reveal that photoinduced electron transfer does not occur in toluene, but occurs in more polar solvents such as 2-methyltetrahydrofuran, wherein tau = 55 ps for charge separation and tau = 99 ps for charge recombination

  受其分子结构限制为对称 pi 堆叠几何形状的发色二聚体的光激发通常产生独立于溶剂极性的准分子，而具有边到边垂直 pi 系统的二聚体在高极性溶剂中经历激发态对称性破坏，导致二聚体内部电荷分离. 我们提供了对称性在 1,7-双（吡咯烷-1'-基）-苝-3,4:9,10-双（二甲酰亚胺）（5PDI）的对称共面二聚体的最低激发单线态破坏的直接证据在低极性溶剂甲苯中定量产生自由基离子对。这种二聚体，cof-5PDI2，是通过将两个 5PDI 发色团通过酰亚胺基团连接到呫吨间隔物上而合成的。为了比较，线性对称二聚体 lin-5PDI2，制备了其中 5PDI 发色团通过它们的酰亚胺之间的 NN 单键端对端连接。lin-5PDI2 内的 5PDI 生色团的边缘到边缘 pi 系统彼此垂直。两种 5PDI 二聚体的基态吸收光谱均显示激子耦合，这与 5PDI 生色团相对于彼此的取向一致。用 700 nm、100
• Rigid Oligoperylenediimide Rods: Anion–π Slides with Photosynthetic Activity
  作者：Alejandro Perez-Velasco、Virginie Gorteau、Stefan Matile

  DOI：10.1002/anie.200703749

  日期：2008.1.18
• Electron-Donating Perylene Tetracarboxylic Acids for Dye-Sensitized Solar Cells
  作者：Yuki Shibano、Tomokazu Umeyama、Yoshihiro Matano、Hiroshi Imahori

  DOI：10.1021/ol070556s

  日期：2007.5.1

  Novel perylene imide derivatives with both electron-donating and bulky substituents have been synthesized for dye-sensitized solar cells. The power conversion efficiency reached 2.6%, which is the highest value among perylene-sensitized TiO2 solar cells.
• Ultrafast Photoinduced Charge Separation Resulting from Self-assembly of a Green Perylene-based Dye into π-Stacked Arrays
  作者：Michael J. Fuller、Louise E. Sinks、Boris Rybtchinski、Jovan M. Giaimo、Xiyou Li、Michael R. Wasielewski

  DOI：10.1021/jp044796q

  日期：2005.2.1

  Condensation of 3,4.5-tris(n-dodecyloxy)aniline with the green chromophore 1,7-bis(N-pyrrolidinyl)perylene-3,4,9, 10-tetracarboxylic dianhydride yields N,N'-bis(3,4,5-tris(n-dodecyloxy)phenyl)-1,7-bis(N-pyrrolidinyl)perylene-3,4;9,10-bis(dicarboximide), 5PDI-TAP, which absorbs light strongly from 550 to 750 rim. 5PDI-TAP dissolves readily in methylcyclohexane (MCH), resulting in self-assembly into H-aggregates. Small-angle X-ray scattering data obtained on 10(-4) M solutions of 5PDI-TAP in MCH show that the aggregates are pi-stacked monodisperse pentamers. Femtosecond transient absorption spectroscopy on solutions of (5PDI-TAP)(5) in MCH shows evidence of charge separation occurring with tau less than or equal to 150 fs, between adjacent stacked members of 5PDI-TAP within the pentamer followed by charge recombination with tau = 860 ps. Transmission electron microscopy of 5PDI-TAP films cast from solution show isolated bundles of columnar aggregates. (5PDI-TAP)(n) is a potentially useful material for organic photovoltaics because efficient photoinduced charge veneration is an intrinsic property of the assembly.