tetrabutyl 2,6-dibromonaphthalene-1,4,5,8-tetracarboxylate | 1224622-75-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tetrabutyl 2,6-dibromonaphthalene-1,4,5,8-tetracarboxylate
• 英文别名: 2,6-dibromo-1,4,5,8-tetra (n-butoxycarbonyl) naphthalene
• CAS: 1224622-75-6
• 化学式: C₃₀H₃₈Br₂O₈
• 分子量: 686.435
• InChiKey: VHBSZAKRTRRLLB-UHFFFAOYSA-N

物化性质

• 沸点：
  680.1±50.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  tetrabutyl 2,6-dibromonaphthalene-1,4,5,8-tetracarboxylate 在 copper(l) iodide 、 四(三苯基膦)钯 、 palladium on activated charcoal 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.5h， 生成 4,9-bis(4-hexyldodecyl)isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone
  参考文献：
  名称：

  可溶性perinone异构体作为p-i-n钙钛矿太阳能电池的电子传输材料

  摘要：

  我们合成了三种可溶性环萘酮异构体作为 p-i-n 钙钛矿太阳能电池中的电子传输材料。顺式异构体BBIN-2 具有比反式异构体更高的 LUMO 能级和电子迁移率。BBIN-2 器件显示出 19.36% 的最高功率转换效率，证明了环萘酮染料在钙钛矿太阳能电池中的潜力。

  DOI：

  10.1039/d3cc00862b
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 1,3-二溴-5,5-二甲基海因 、 硫酸 、 四正辛基溴化铵 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 14.0h， 生成 tetrabutyl 2,6-dibromonaphthalene-1,4,5,8-tetracarboxylate
  参考文献：
  名称：

  基于苯并噻二唑咪唑衍生物的强受体

  摘要：

  尽管有机半导体发展迅速，但开发高空气稳定性的n型有机半导体仍然具有挑战性。在此，报道了基于苯并噻二唑咪唑单元的新型强受体。结果表明，强受体BTI-NDI-BTI-a具有良好的溶解度和高电子亲和力（3.94 eV），并伴有一维滑移堆积晶体。值得注意的是，该材料在开发空气稳定的n型有机半导体材料方面具有广阔的潜力。

  DOI：

  10.3390/molecules29102262

文献信息

• Core-Perfluoroalkylated Perylene Diimides and Naphthalene Diimides: Versatile Synthesis, Solubility, Electrochemistry, and Optical Properties
  作者：Zhongyi Yuan、Jing Li、Yi Xiao、Zheng Li、Xuhong Qian

  DOI：10.1021/jo100231j

  日期：2010.5.7

  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.
• CONJUGATED POLYMERS
  申请人：INNOVATIONLAB GMBH

  公开号：US20170331043A1

  公开（公告）日：2017-11-16

  The invention relates to new conjugated semiconducting polymers containing thermally cleavable side groups. The thermally cleavable side groups are selected from among carbonate groups and carbamate groups, By thermally cleaving side groups, the solubility or the polymers can he reduced in a targeted manner. The polymers are used as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, organic photodetectors (OPDs), organic light emitling diodes (OLEDs), and organic field effect transistors (OFETs).
• Soluble perinone isomers as electron transport materials for p–i–n perovskite solar cells
  作者：Xinxin Zhang、Tianyu Xu、Ziqi Tian、Xiang He、Shengxiong Zhang、Ling Ai、Wenjun Zhang、Shiyong Liu、Weijie Song

  DOI：10.1039/d3cc00862b

  日期：——

  three soluble perinone isomers as electron transport materials in p–i–n perovskite solar cells. The cis-isomer BBIN-2 possesses higher LUMO level and electron mobility than the trans-isomers. The BBIN-2 devices showed the highest power conversion efficiency of 19.36%, demonstrating the potential of perinone dyes in perovskite solar cells.

  我们合成了三种可溶性环萘酮异构体作为 p-i-n 钙钛矿太阳能电池中的电子传输材料。顺式异构体BBIN-2 具有比反式异构体更高的 LUMO 能级和电子迁移率。BBIN-2 器件显示出 19.36% 的最高功率转换效率，证明了环萘酮染料在钙钛矿太阳能电池中的潜力。
• 10.3390/molecules29102262
  作者：Du, Hanyun、Chen, Bin、Zhang, Fengyuan

  DOI：10.3390/molecules29102262

  日期：——

  Despite the rapid progression of organic semiconductors, developing high-air-stability n-type organic semiconductors are still challenging. Herein, novel strong acceptors based on benzothiadiazoloimidazole units are reported. The results reveal that the strong acceptor BTI-NDI-BTI-a has good solubility and high electron affinity (3.94 eV), accompanied by 1D slipped-stacking crystals. Notably, the material

  尽管有机半导体发展迅速，但开发高空气稳定性的n型有机半导体仍然具有挑战性。在此，报道了基于苯并噻二唑咪唑单元的新型强受体。结果表明，强受体BTI-NDI-BTI-a具有良好的溶解度和高电子亲和力（3.94 eV），并伴有一维滑移堆积晶体。值得注意的是，该材料在开发空气稳定的n型有机半导体材料方面具有广阔的潜力。