3,8-dibromophenanthridin-6(5H)-one | 23818-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,8-dibromophenanthridin-6(5H)-one
• 英文别名: 3,8-dibromo-5H-phenanthridin-6-one；3,8-Dibrom-phenanthridon；3,8-dibromo-5H-phenanthridin-6-one
• CAS: 23818-37-3
• 化学式: C₁₃H₇Br₂NO
• 分子量: 353.013
• InChiKey: YGNOBSNWUISURG-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±35.0 °C(Predicted)
• 密度：
  1.848±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,8-dibromophenanthridin-6(5H)-one 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,8-dibromo-6-((2-octyldodecyl)oxy)phenanthridine
  参考文献：
  名称：

  调节分子内电荷转移和共振效应，实现高性能全聚合物太阳能电池的超宽带隙共轭聚合物

  摘要：

  全聚合物太阳能电池（APSC）由于卓越的稳定性和机械灵活性而受到越来越多的关注。然而，APSC 的功率转换效率 (PCE) 落后，归因于有效聚合物供体 ( PD ) 有限。特别是高性能PD的报道还很少见。具有超宽带隙，这对于最大限度地收集高能光子以实现更好的光利用是必不可少的。在此，强调了分子内电荷转移和醌型共振效应在调节供体-受体共轭材料带隙中的重要性，并报道了一种基于苯基/吡啶稠合菲啶（PD）部分的新型聚合物供体PBPD。因此，PBPD 具有高达 2.24 eV 的超宽光学带隙和 487-523 nm 的强吸收率，这恰好遵循太阳光谱的最强辐射。高能光子的放大光利用使基于PBPD:PY-IT的APSC具有15.29%的高功率转换效率，在超宽带隙P D的APSC中名列前茅，挑战了典型的PD s 带隙约为 1.80 eV。得益于PBPD独特的光响应和分子取向，含有PBPD的三元APSC获得了

  DOI：

  10.1002/adfm.202301701
• 作为产物：
  描述：

  2,7-二溴-9-芴酮 在 sodium azide 、 硫酸 作用下， 反应 2.0h， 以76%的产率得到3,8-dibromophenanthridin-6(5H)-one
  参考文献：
  名称：

  基于5-烷基菲咯啶-6（5H）-1和6-烷氧基菲啶的异构体合成中等带隙π共轭聚合物

  摘要：

  通过对前体3,8-dibromophenanthrindi-6（5H）-one进行烷基化反应，合成了由5-烷基菲咯啉-6（5H）-1（PN）和6-烷氧基菲啶（PO）异构体组成的两种新型二溴单体。通过NMR光谱确认了分子结构。中带隙共轭聚合物PDBTPN和PDBTPO是利用PN和PO这两种异构体作为供电子单元，二噻吩苯并[2,1,3]二噻唑作为电子接受单元而构建的。所得聚合物表现出类似的吸收谱，其光学带隙为1.90 eV，而PDBTPO表现出略高的吸收系数。循环伏安法测量表明，这些聚合物具有相对较深的最高占据的分子轨道能级，约为-5.70 eV。基于这两种聚合物的聚合物太阳能电池显示出相对较高的开路电压，约为0.90V。所有器件均表现出中等性能，基于PDBTPO的最佳功率转换效率为3.77％。基于PDBTPO的器件的功率转换效率比基于PDBTPN的器件略高，这可以归因于前者具有更高的空穴迁移率和更有利的薄膜形态。©2016

  DOI：

  10.1002/pola.28079

文献信息

• Complex aryl copolymer compounds and polymer light emitting devices made by using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2325226A1

  公开（公告）日：2011-05-25

  The present invention provides a compound which is (a) represented by the below formula (23-1), (23-2), (23-3), (24-1), (24-2), (24-3), or (25): in the formula, X13 represents a boron atom, a nitrogen atom, or a phosphorus atom; Y3 and Y4 each independently represent a halogen atom, alkylsulfonate group, arylsulfonate group, arylalkylsulfonate group, boric ester group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated methyl group, boric acid group, formyl group, or vinyl group; R45, R46, R47, R48, R49, and R50, each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, acyl group, acyloxy group, amide group, imide group, Imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, aryl ethynyl group, carboxyl group, or cyano group; R46, and R47, or R48 and R49 may be connected mutually to form a ring; R51 represents an alkyl group, aryl group, arylalkyl group, or a monovalent heterocyclic group; Z3 represents a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, substituted amino group, substituted silyl group, a monovalent heterocyclic group, arylalkenyl group, or aryl ethynyl group; Z4 represents a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, substituted amino group, substituted silyl group, a monovalent heterocyclic group, arylalkenyl group, or aryl ethynyl group; in the formula, X14 represents a boron atom, nitrogen atom, or phosphorus atom; Y5 and Y6 each independently represent a halogen atom, alkylsulfonate group, arylsulfonate group, arylalkylsulfonate group, boric ester group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated methyl group, boric acid group, formyl group, or vinyl group; R52, R53, R54, R55, R56, and R57 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, acyl group, acyloxy group, amide group, imide group, Imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, aryl ethynyl group, carboxyl group, or cyano group; R53, and R54, R55 and R56 may be connected mutually to form a ring; R58 represents an alkyl group, aryl group, arylalkyl group, or a monovalent heterocyclic group; Z5 represents a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, substituted amino group, substituted silyl group, monovalent heterocyclic group, arylalkenyl group, or aryl ethynyl group; Z6 represents a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, substituted amino group, substituted silyl group, monovalent heterocyclic group, arylalkenyl group, or aryl ethynyl group; in the formula, Y7 and Y8 each independently represent a halogen atom, alkylsulfonate group, arylsulfonate group, arylalkylsulfonate group, boric ester group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated methyl group, boric acid group, formyl group, or vinyl group; R59, R60, R61, R62, R63, and R64 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, aryl ethynyl group, carboxyl group, or cyano group; R60, and R61, R62 and R63 may be connected mutually to form a ring.

  本发明提供了一种 (a) 由下式（23-1）、（23-2）、（23-3）、（24-1）、（24-2）、 （24-3）或（25）表示的化合物： 式中，X13 代表硼原子、氮原子或磷原子； Y3 和 Y4 各自独立地代表卤素原子、烷基磺酸基团、芳基磺酸基团、芳烷基磺酸基团、硼酯基团、锍甲基、鏻甲基、鏻酸甲基、单卤代甲基、硼酸基团、甲酰基或乙烯基；R45、R46、R47、R48、R49 和 R50 各自独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、酰基、酰氧基、酰胺基亚胺基、亚胺残基、氨基、取代的氨基、取代的硅烷基、取代的硅氧基、取代的硅硫基、取代的硅氨基、一价杂环基、芳基烯基、芳基乙炔基、羧基或氰基；R46 和 R47 或 R48 和 R49 可相互连接形成一个环； R51 代表烷基、芳基、芳烷基或单价杂环基团； Z3 代表氢原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、取代的氨基、取代的硅基、一价杂环基团、芳基烯基或芳基乙炔基； Z4 代表氢原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、取代氨基、取代硅基、一价杂环基团、芳基烯基或芳基乙炔基； 式中，X14 代表硼原子、氮原子或磷原子；Y5 和 Y6 各自独立地代表卤素原子、烷基磺酸基、芳基磺酸基、芳烷基磺酸基、硼酸酯基、锍甲基、鏻甲基、膦酸甲基、单卤代甲基、硼酸基、甲酰基或乙烯基；R52、R53、R54、R55、R56 和 R57 各自独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、酰基、酰氧基、酰胺基、亚胺基、亚胺残基、氨基、取代的氨基、取代的硅烷基、取代的硅氧基、取代的硅硫基、取代的硅烷基 R53、R54、R55 和 R56 可相互连接形成一个环；R58 代表烷基、芳基、芳烷基或单价杂环基团； Z5 代表氢原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、取代的氨基、取代的硅基、一价杂环基团、芳基烯基或芳基乙炔基； Z6 代表氢原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、取代氨基、取代硅烷基、一价杂环基团、芳基烯基或芳基乙炔基； 式中，Y7 和 Y8 各自独立地代表卤素原子、烷基磺酸基、芳基磺酸基、芳烷基磺酸基、硼酸酯基、甲基锍基、甲基鏻基、甲基膦酸基、单卤代甲基、硼酸基、甲酰基或乙烯基；R59、R60、R61、R62、R63 和 R64 各自独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、酰基、酰氧基、酰胺基、酰亚胺基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、亚胺基、亚胺残基、氨基、取代的氨基、取代的硅烷基、取代的硅氧基、取代的硅硫基、取代的硅氨基、一价杂环基、芳基烯基、芳基乙炔基、羧基或氰基；R60、R61、R62 和 R63 可相互连接形成一个环。
• Aryl copolymer compounds and polymer light emitting devices made by using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2325224A1

  公开（公告）日：2011-05-25

  The present invention provides a polymer compound comprising a repeating unit of below formula (1) or (2), and a repeating unit represented by the below formula (5), and having a polystyrene reduced number average molecular weight of 103 to 108: wherein, Ar1 and Ar2 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group; X1 and X2 each independently represent O, S, C(=O), S(=O), SO2, C(R1)(R2), Si(R3)(R4), N(R5), B(R6), P(R7) or P(=O)(R8); R1, R2, R3, R4, R5, R6, R7 and R8 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, ammo group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group; R1 and R2, or R3 and R4 may be connected mutually to form a ring; X1 and X2 are not the same; and wherein X1 and Ar2 bond to adjacent carbons in the aromatic ring of Ar1, and X2 and Ar1 bond to adjacent carbons in the aromatic ring of Ar2; wherein, Ar3 and Ar4 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group; X3 and X4 each independently represent N, B, P, C(R9) or Si(R10); R9 and R10 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group; X3 and X4 are not the same; and wherein X3 and Ar4 bond to adjacent carbons in the aromatic ring of Ar3, and X4 and Ar3 bond to adjacent carbons in the aromatic ring of Ar4;         -Ar5-     (5) wherein Ar5 represents an arylene group, divalent heterocyclic group, or divalent group having metal complex structure.

  本发明提供了一种聚合物化合物，它由下式（1）或（2）的重复单元和下式（5）代表的重复单元组成，其聚苯乙烯还原数平均分子量为 103 至 108： 其中，Ar1 和 Ar2 各自独立地代表三价芳烃基团或三价杂环基团；X1 和 X2 各自独立地代表 O、S、C(＝O)、S(＝O)、SO2、C(R1)(R2)、Si(R3)(R4)、N(R5)、B(R6)、P(R7)或 P(＝O)(R8)；R1、R2、R3、R4、R5、R6、R7 和 R8 各自独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、酰基、酰氧基、酰胺基、酸亚胺基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酰亚胺残基、酸亚胺基、亚胺残基、胺基、取代的氨基、取代的硅烷基、取代的硅氧基、取代的硅硫基、取代的硅氨基、一价杂环基、芳基烯基、芳基乙炔基、羧基或氰基；R1 和 R2 或 R3 和 R4 可相互连接形成环；X1 和 X2 不相同；其中 X1 和 Ar2 与 Ar1 的芳香环中的相邻碳键合，X2 和 Ar1 与 Ar2 的芳香环中的相邻碳键合； 其中，Ar3 和 Ar4 各自独立地代表三价芳香烃基团或三价杂环基团；X3 和 X4 各自独立地代表 N、B、P、C(R9) 或 Si(R10)；R9 和 R10 各自独立地代表氢原子、卤素原子、烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、芳烷基、芳烷氧基、芳烷硫基、酰基、酰氧基、酰胺基、酸亚胺基亚胺残基、氨基、取代的氨基、取代的硅烷基、取代的硅氧基、取代的硅硫基、取代的硅氨基、一价杂环基、芳烷基、芳炔基、羧基或氰基；X3 和 X4 不相同；其中 X3 和 Ar4 与 Ar3 的芳香环中的相邻碳键合，X4 和 Ar3 与 Ar4 的芳香环中的相邻碳键合； -Ar5- (5) 其中 Ar5 代表芳烯基团、二价杂环基团或具有金属络合物结构的二价基团。
• CH150168
  申请人：——

  公开号：——

  公开（公告）日：——
• Patternable Conjugated Polymers with Latent Hydrogen-Bonding on the Main Chain
  作者：Kun Yang、Tianda He、Xiaoyi Chen、Stephen Z. D. Cheng、Yu Zhu

  DOI：10.1021/ma501960t

  日期：2014.12.23

  Conjugated polymers with latent hydrogen-bonding on the main chain were synthesized using Suzuki coupling reaction. The resulting polymers with latent hydrogen-bonding can be converted to the actual hydrogen-bonded polymers by thermal annealing or UV irradiation. As the hydrogen-bonding sites are fused with p-conjugated units on the polymer backbone, the intermolecular interactions between the polymer chains will be strongly enhanced when the hydrogen-bonds are formed. By removing the protection group and forming hydrogen-bonding, the polymers exhibited a bathochromic shift over those with latent hydrogen-bonding, indicating a hydrogen-bonding-mediated enhancement of pp stacking. In addition, the fused hydrogen-bond sites and p-conjugated units led to closely packed polymer chains, resulting in insoluble pigment-like polymers. This drastic solubility change from polymers with latent hydrogen-bonding to hydrogen-bonded polymers can be used to pattern conjugated polymers directly. The photolithography of the conjugated polymer with latent hydrogen-bonding was demonstrated, and the patterned electrochromic devices were fabricated and tested.
• US1880441
  申请人：——

  公开号：——

  公开（公告）日：——