1-bromo-3,4,9,10-tetra(n-butoxy-carbonyl)-perylene | 1080663-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-bromo-3,4,9,10-tetra(n-butoxy-carbonyl)-perylene
• 英文别名: 1-bromo-3,4,9,10-tetrakis(n-butoxycarbonyl)perylene；tetrabutyl 1-bromoperylene-3,4,9,10-tetracarboxylate
• CAS: 1080663-37-1
• 化学式: C₄₀H₄₃BrO₈
• 分子量: 731.681
• InChiKey: ZDRDYZVLUQRRHO-UHFFFAOYSA-N

物化性质

• 沸点：
  787.5±55.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  全氟辛基碘烷 、 1-bromo-3,4,9,10-tetra(n-butoxy-carbonyl)-perylene 在 铜 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以23%的产率得到Tetrabutyl 1-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)perylene-3,4,9,10-tetracarboxylate
  参考文献：
  名称：

  Core-Perfluoroalkylated Perylene Diimides and Naphthalene Diimides: Versatile Synthesis, Solubility, Electrochemistry, and Optical Properties

  摘要：

  By a strategy featuring perfluoroalkylation of the highly soluble intermediates and their further efficient transformations to target compounds, a versatile synthesis of core-perfluoroalkylated perylene diimides (PDIs) and naphthalene diimides (NDIs) was developed, and PDIs perfluoroalkylated at 1-position or 1,6-positions and core-perfluoroalkylated NDIs were first obtained. By esterification, perfluoroalkylation, hydrolysis, and condensation with amine, 1-perfluorooctyl-PDIs (7b, 7c, and 7e), 1,7-bis(perfluorooctyl)-PDIs (8a-c and 8e-g), 1,6-bis(perfluorooctyl)PDIs (8'e), a mixture of 1,7-bis(trifluoromethyl)-PDIs and 1,6-bis(trifluoromethyl)-PDIs (11b and 11'b), 11d and 11'd, in a ratio of 19:1), 2-perfluorooctyl-NDIs (20a-d), and 2,6-bis(perfluorooctyl)-NDIs (21a-21d) were efficiently synthesized. Five valuable intermediates-1-perfluorooctylperylene dianhydride (5), 1,7-bis(perfluorooctyl)perylene dianhydride (6) 1,6-bis(perfluorooctyl)perylene dianhydride (6'), 2-perfluorooctylnaphthalene dianhydride (18), and 2,6-bis(perfluorooctyl) naphthalene dianhydride (19)-were also obtained, and they can condense with many amines to produce PDIs containing different functional side chains on the imide nitrogen atoms. Solubility, electrochemistry, and optical properties of the above core-perfluoroalkylated PDIs and NDIs were investigated. Core-perfluoroalkylated 8e, 8f, 8'e, mixture of 11d and 11'd, 20b, and 20d with excellent solubility in common organic solvents are competitive as candidates as solution processable semiconductors. Core-perfluoroalkylated PDIs and NDIs with experimental LUMO energy of 4.04-4.34 eV demonstrate strong electron accepting ability. For core-perfluoroalkylated PDIs, the maximum absorptions display blue shifts of 6-18 nm and the maximum molar extinction coefficients decrease obviously relative to those of unsubstituted PDIs, and they inherit the strong fluorescence from the PDIs family, which makes them promising fluorescent dyes.

  DOI：

  10.1021/jo100231j
• 作为产物：
  描述：

  tetrabutyl perylene-3,4,9,10-tetracarboxylate 在 溴 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以25%的产率得到1-bromo-3,4,9,10-tetra(n-butoxy-carbonyl)-perylene
  参考文献：
  名称：

  二甲基氨基苯乙烯基BODIPY-per四羧酸衍生物二元化合物的实验和理论研究：合成，性质和DFT计算†

  摘要：

  合成了二甲基氨基苯乙烯基BODIPY - per四羧酸衍生物（PTAC和PBI）二联体OMePTAC-BODIPY，PTAC-BODIPY和PBI-BODIPY，并通过光谱和DFT方法对其进行了研究。UV-Vis吸收光谱表明，通过将per四羧酸衍生物掺入BODIPY嵌段中，从350nm至600nm区域的吸收系数显着提高。由于光诱导的电子转移效应，二元组的荧光被强烈淬灭。差分脉冲伏安图（DPV）用于评估二元组的能量水平。氧化峰几乎完全相同，位于0.53 eV对。Ag / AgCl的还原峰分别出现在OmePTAC-BODIPY，PTAC-BODIPY和PBI-BODIPY的-1.1 eV，-1.0 eV和-0.5 eV的正电位值上，表明二甲基氨基苯乙烯BODIPY的LUMO含量通过从BODIPY的介观位置改变受体单元，精确设计了-per四羧酸衍生物二元组。单线态氧（1 O 2）实验发现，随着电子受体单元电子亲和力的增加，1

  DOI：

  10.1039/c5ra25139g

文献信息

• A design concept of planar conjugated ladder oligomers of perylene bisimides and efficient synthetic strategy via regioselective photocyclization
  作者：Zhongyi Yuan、Yi Xiao、Xuhong Qian

  DOI：10.1039/b925605a

  日期：——

  By photocyclization, benzene, thieno[3,2-b]thiophene, and fluorene units were embedded between the two perylene units. Symmetric oligomeric perylene bisimide 6 displays broad absorption and strong electron-accepting ability.

  通过光环化，将苯，噻吩并[3,2-b]噻吩和芴单元嵌入两个per单元之间。对称的低聚per双酰亚胺6具有广泛的吸收能力和较强的电子接受能力。
• Fusing three perylenebisimide branches and a truxene core into a star-shaped chromophore with strong two-photon excited fluorescence and high photostability
  作者：Yuanpeng Xie、Xinfu Zhang、Yi Xiao、Youdi Zhang、Fan Zhou、Jing Qi、Junle Qu

  DOI：10.1039/c2cc31261a

  日期：——

  A novel star-shaped chromophore, Tr–PBI, was constructed by fusing three perylenebisimide branches and a truxene core. Tr–PBI exhibits high photostability and excellent two-photon properties: the maximum of δTPA is 11 000 GM at 990 nm and fluorescence quantum efficiency Φ is 0.40 in THF.

  一种新型星形发色团 Tr-PBI 是由三个过二亚胺分支和一个三亚甲苯核心融合而成。Tr-PBI 具有很高的光稳定性和出色的双光子特性：在 990 纳米波长下，δTPA 的最大值为 11 000 GM，在 THF 中的荧光量子效率Φ为 0.40。
• 苝四羧酸-氟硼吡咯二元染料及其制备方法
  申请人：黄河科技学院

  公开号：CN107057397A

  公开（公告）日：2017-08-18

  本发明公开了苝四羧酸‑氟硼吡咯二元染料及其制备方法，该二元染料具有如下结构通式Ⅰ和通式Ⅱ：式中的R1和R2为烷基，R3为烷氧基或氢基。本发明公开了三种新的化合物，拓展化合物的范围，为新化合物性能研究提供了基础。
• Modular Synthesis and Structure-Property Correlation of Pyrene - Rylene Dyes for Cellular Imaging
  作者：Tankut Türel、Gomathi Mahadevan、Suresh Valiyaveettil

  DOI：10.1002/ejoc.202000367

  日期：2020.6.16

  Propeller shape compounds with extended conjugation shows high fluorescent intensity in the solid state due to the suppressed aggregation. The synthesis and full characterization of four compounds having multiple photoactive units in conjugation with a central pyrene group are reported.

  由于抑制的聚集，具有延长的共轭的螺旋桨形状的化合物在固态下显示出高荧光强度。报道了四种具有多个光敏单元与中心pyr基共轭的化合物的合成和完整表征。
• Broad-band Chiral Absorbance of Visible Light
  作者：Sae Young Han、Rachael K. Mow、Amymarie K. Bartholomew、Fay Ng、Michael L. Steigerwald、Xavier Roy、Colin Nuckolls、Ren A. Wiscons

  DOI：10.1021/jacs.2c01650

  日期：2022.3.30

  the design of chiral chromophores. However, for dyes to be practically relevant in chiroptical applications, they must also absorb and/or emit chiral light over broad wavelength ranges. We investigate the interplay between molecular symmetry and broad-band chiral absorbance in a series of [6]helicenes. We find that an asymmetric [6]helicene containing two distinct chromophores absorbs chiral light

  手性吸光度和发射的放大是设计手性发色团的主要品质因数。然而，对于在手性光学应用中实际相关的染料，它们还必须在宽波长范围内吸收和/或发射手性光。我们研究了一系列 [6] 螺旋烯中分子对称性和宽带手性吸光度之间的相互作用。我们发现含有两个不同发色团的不对称 [6] 螺旋烯比这里研究的对称 [6] 螺旋烯在更宽的波长范围内吸收手性光。化学还原螺旋烯将 ECD 光谱的吸收边缘移动到近红外波长范围内，同时保持广泛的手性吸收，从而产生在整个可见光波长范围内吸收单手性光的 [6] 螺旋烯。