2,7-dibromo-3,6-dimethyl-9H-carbazole | 544436-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,7-dibromo-3,6-dimethyl-9H-carbazole
• CAS: 544436-44-4
• 化学式: C₁₄H₁₁Br₂N
• 分子量: 353.056
• InChiKey: WLRLZFDYXVDYMC-UHFFFAOYSA-N

物化性质

• 沸点：
  478.7±40.0 °C(Predicted)
• 密度：
  1.757±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,7-dibromo-3,6-dimethyl-9H-carbazole 在 1,10-菲罗啉 、 tin(II) chloride dihdyrate 、 potassium carbonate 、 copper(l) chloride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 96.0h， 生成 bis-(4-(2-butyloctyloxy)phenyl)-3-(2,7-dibromo-3,6-dimethyl-9H-carbazol-9-yl)aniline
  参考文献：
  名称：

  Aryl amine substituted low energy gap carbazole polymers: preparation and photovoltaic properties

  摘要：

  本文介绍了一系列供体/受体共聚物的制备方法，这些共聚物由交替连接的 2,7 链 3,6 二甲基-9-芳基氨基咔唑单元和 5,7 双-（噻吩-2-基）-2,3-二苯基噻吩并[3,4-b]吡嗪单元组成。三芳基胺取代基通过对位或元位连接到咔唑重复单元上。本文研究了三芳基胺取代基在该系列聚合物中的连接位置的影响，以及用烷氧基取代 5,7-双(噻吩-2-基)-2,3-二苯基噻吩并[3,4-b]吡嗪重复单元 2,3 位上的苯基的影响。聚合物的表征采用核磁共振光谱、紫外可见吸收光谱和荧光光谱，分子量的估算采用凝胶渗透色谱法。聚合物 P1-P4 可吸收高达 900 纳米的光线，能量隙在 1.37 至 1.40 eV 之间。在白光照明下，ITO/PEDOT:PSS/P2:PC70BM(1/4, w/w)/Al光伏电池的开路电压为0.60 V，功率转换效率为0.67%，短路电流为3.6 mA cm-2。

  DOI：

  10.1039/c0jm01335h
• 作为产物：
  描述：

  2,2'-Diamino-4,4'-dibromo-5,5'-dimethyl-biphenyl 、 十二烷基苯磺酸 在 silica gel—toluene hexane 作用下， 以 1-叔丁基-3,5-二甲苯 为溶剂， 反应 48.0h， 以to give 2,7-dibromo-3,6-dimethyl-carbazole as a colourless powder (4.06 g, 85% yield)的产率得到2,7-dibromo-3,6-dimethyl-9H-carbazole
  参考文献：
  名称：

  2, 7-Substituted carbazoles and oligomers, polymers and co-polymers thereof

  摘要：

  式I中的一个carbazole，其中R1和R2各自独立地是卤素、B（OH）2、B（OR7）2、Sn（R6）、C1-20烃基或含有一个或多个杂原子的C1-20烃基，R3为H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R4和R5各自独立地是H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R7和R8各自独立地是C1-20烃基，但当R3为正辛基时，R4和R5不能同时为H，并且还包括其共轭寡聚物、聚合物和共聚物。例如，这些寡聚物、聚合物和共聚物的实施形式可以形成薄膜，这些薄膜可以用于电子器件中。

  公开号：

  US20050119491A1

文献信息

• A novel 2,7-linked carbazole based “double cable” polymer with pendant perylene diimide functional groups: preparation, spectroscopy and photovoltaic properties
  作者：David K. Mohamad、Achim Fischereder、Hunan Yi、Ashley J. Cadby、David G. Lidzey、Ahmed Iraqi

  DOI：10.1039/c0jm02673e

  日期：——

  The preparation and chemical analysis of a ‘double-cable’ conjugated polymer comprising a backbone of alternating 2,7-linked carbazole repeat units with covalently attached perylene diimide (PDI) substituents and dithienyl repeat units is presented. The backbone of the new “double-cable” polymer P1 acts as an electron donor while the pendant PDI substituents act as electron acceptors. In order to investigate the influence of the PDI moieties on the polymer backbone as well as to elucidate their photophysical interaction, three reference-compounds were also prepared and analysed: a polymer with the same backbone as that of P1 but without PDI substituents (P2) and two PDI derivatives with branched alkyl side chains (PDI 2 with 12-tricosanyl substituents and PDI 1 with 3-pentyl substituents). We find that polymer P1 shows pronounced electron transfer from the polymer backbone to the PDI chromophore units covalently bound to it, resulting in highly efficient quenching of excitons and strong suppression of fluorescence in solutions and in thin films. The existence of long-lived polaronic states resulting from exciton dissociation on P1 is confirmed using steady state photo-induced absorption spectroscopy. Despite the improved exciton quenching yield shown by P1 over a blend of P2/PDI, photovoltaic devices fabricated from P1 have a low external quantum efficiency (EQE) of around 0.43% at 410 nm; a value that is smaller than that from a conventional BHJ device of P2/PDI which is found to have a peak external quantum efficiency of 3.7% at 463 nm. We tentatively ascribe the reduced EQE of the double-cable polymer to geminate recombination of charge-carriers as a result of poor charge transport and a complete lack of donor acceptor phase separation.

  本文介绍了一种 "双缆 "共轭聚合物的制备和化学分析方法，这种聚合物的骨架由交替连接的2,7-咔唑重复单元和共价连接的过二亚氨基（PDI）取代基及二噻吩重复单元组成。新型 "双缆 "聚合物 P1 的骨架充当电子供体，而悬挂的 PDI 取代基则充当电子受体。为了研究 PDI 分子对聚合物主链的影响以及阐明它们之间的光物理相互作用，我们还制备并分析了三种参考化合物：一种主链与 P1 相同但不含 PDI 取代基的聚合物（P2），以及两种带有支链烷基侧链的 PDI 衍生物（带有 12 个三聚氰胺取代基的 PDI 2 和带有 3 个戊基取代基的 PDI 1）。我们发现，聚合物 P1 显示出明显的电子转移现象，电子从聚合物骨架转移到与其共价结合的 PDI 发色团单元，从而高效淬灭激子，并强烈抑制溶液和薄膜中的荧光。利用稳态光诱导吸收光谱，证实了 P1 上的激子解离产生的长寿命极子态的存在。尽管 P1 比 P2/PDI 混合物显示出更高的激子淬灭产率，但由 P1 制成的光伏器件在 410 纳米波长处的外部量子效率（EQE）却很低，约为 0.43%；该值小于 P2/PDI 传统 BHJ 器件，后者在 463 纳米波长处的外部量子效率峰值为 3.7%。我们初步认为，双缆聚合物的 EQE 值降低是由于电荷传输不畅和完全缺乏供体受体相分离造成的电荷载流子的宝石状重组。
• 2, 7 - SUBSTITUTED CARBAZOLES AND OLIGOMERS, POLYMERS AND CO-POLYMERS THEREOF
  申请人：THE UNIVERSITY OF SHEFFIELD

  公开号：EP1453802A1

  公开（公告）日：2004-09-08
• [EN] 2, 7 - SUBSTITUTED CARBAZOLES AND OLIGOMERS, POLYMERS AND CO-POLYMERS THEREOF<br/>[FR] CARBAZOLES 2,7-SUBSTITUES ET LEURS OLIGOMERES, POLYMERES ET COPOLYMERES
  申请人：UNIV SHEFFIELD

  公开号：WO2003050086A1

  公开（公告）日：2003-06-19

  A carbazole of formula I wherein R1 and R2 are each independently halo, B(OH)2, B(OR7)2, Sn(R8)3, C1-20 hydrocarbyl, or C1-20 hydrocarbyl comprising one or more hetero atoms, R3 is H, halo, C1-20 hydrocarbyl, C1-20 hydrocarbyl comprising one or more heteroatoms, or cyano, R4 and R5 are each independently H, halo, C1-20 hydrocarbyl, C1-20 hydrocarbyl comprising one or more heteroatoms, or cyano, and R7 and R8 are each independently C1-20 hydrocarbyl, provided that R4 and R5 are not both H when R3 is n-octyl, and conjugated oligomers, polymers and co-polymers thereof. Embodiments of the oligomers, polymers and co-polymers can, for example, be formed into films which can be incorporated into electronic devices.
• Aryl amine substituted low energy gap carbazole polymers: preparation and photovoltaic properties
  作者：David Mohamad、Richard G. Johnson、Dainius Janeliunas、Mindaugas Kirkus、Hunan Yi、David G. Lidzey、Ahmed Iraqi

  DOI：10.1039/c0jm01335h

  日期：——

  The preparation of a series of donor/acceptor copolymers comprising alternating 2,7-linked 3,6-dimethyl-9-arylamino-carbazole units and 5,7-bis-(thiophen-2-yl)-2,3-diphenyl-thieno[3,4-b]pyrazine units is presented. The triarylamine substituents are attached to the carbazole repeat units either through the para- or meta-positions. The effect of the linkage position of triaryl amine substituents in this series of polymers as well as the effect of substitution of the phenyl groups at the 2,3-positions of 5,7-bis-(thiophen-2-yl)-2,3-diphenyl-thieno[3,4-b]pyrazine repeat units with alkoxy-substituents are investigated in this work. The polymers were characterized by NMR spectroscopy, UV-Vis absorption spectroscopy and fluorescence spectroscopy, and their molecular weights were estimated using gel permeation chromatography. Polymers P1–P4 absorb light up to 900 nm and have energy gaps ranging from 1.37 to 1.40 eV. Photovoltaic cells with ITO/PEDOT:PSS/P2:PC70BM(1/4, w/w)/Al showed an open circuit voltage of 0.60 V under white light illumination, power conversion efficiency of 0.67% and short circuit current of 3.6 mA cm−2.

  本文介绍了一系列供体/受体共聚物的制备方法，这些共聚物由交替连接的 2,7 链 3,6 二甲基-9-芳基氨基咔唑单元和 5,7 双-（噻吩-2-基）-2,3-二苯基噻吩并[3,4-b]吡嗪单元组成。三芳基胺取代基通过对位或元位连接到咔唑重复单元上。本文研究了三芳基胺取代基在该系列聚合物中的连接位置的影响，以及用烷氧基取代 5,7-双(噻吩-2-基)-2,3-二苯基噻吩并[3,4-b]吡嗪重复单元 2,3 位上的苯基的影响。聚合物的表征采用核磁共振光谱、紫外可见吸收光谱和荧光光谱，分子量的估算采用凝胶渗透色谱法。聚合物 P1-P4 可吸收高达 900 纳米的光线，能量隙在 1.37 至 1.40 eV 之间。在白光照明下，ITO/PEDOT:PSS/P2:PC70BM(1/4, w/w)/Al光伏电池的开路电压为0.60 V，功率转换效率为0.67%，短路电流为3.6 mA cm-2。
• 2, 7-Substituted carbazoles and oligomers, polymers and co-polymers thereof
  申请人：Iraqi Ahmed

  公开号：US20050119491A1

  公开（公告）日：2005-06-02

  A carbazole of formula I wherein R 1 and R 2 are each independently halo, B(OH) 2 , B(OR 7 ) 2 , Sn(R 6 ), C 1-20 hydrocarbyl, or C 1-20 hydrocarbyl comprising one or more hetero atoms, R 3 is H, halo, C 1-20 hydrocarbyl, C 1-20 hydrocarbyl comprising one or more heteroatoms, or cyano, R 4 and R 5 are each independently H, halo, C 1-20 hydrocarbyl, C l-20 hydrocarbyl comprising one or more heteroatoms, or cyano, and R 7 and R 8 are each independently C 1-20 hydrocarbyl, provided that R 4 and R 5 are not both H when R 3 is n-octyl, and conjugated oligomers, polymers and co-polymers thereof. Embodiments of the oligomers, polymers and co-polymers can, for example, be formed into films which can be incorporated into electronic devices.

  式I中的一个carbazole，其中R1和R2各自独立地是卤素、B（OH）2、B（OR7）2、Sn（R6）、C1-20烃基或含有一个或多个杂原子的C1-20烃基，R3为H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R4和R5各自独立地是H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R7和R8各自独立地是C1-20烃基，但当R3为正辛基时，R4和R5不能同时为H，并且还包括其共轭寡聚物、聚合物和共聚物。例如，这些寡聚物、聚合物和共聚物的实施形式可以形成薄膜，这些薄膜可以用于电子器件中。