4,7-二溴-2-(9-十七烷基)-2H-苯并[1,2,3]三氮唑 | 1312118-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 4,7-二溴-2-(9-十七烷基)-2H-苯并[1,2,3]三氮唑
• 英文名称: 4,7-dibromo-2-(heptadecan-9-yl)-2H-benzo[d][1,2,3]triazole
• 英文别名: 4,7-Dibromo-2-(heptadecan-9-yl)-2H-benzo[d][1,2,3]triazole；4,7-dibromo-2-heptadecan-9-ylbenzotriazole
• CAS: 1312118-15-2
• 化学式: C₂₃H₃₇Br₂N₃
• 分子量: 515.375
• InChiKey: PVLCAXJELPVMIK-UHFFFAOYSA-N

物化性质

• 沸点：
  536.2±53.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  4,7-二溴-2-(9-十七烷基)-2H-苯并[1,2,3]三氮唑 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 三(邻甲基苯基)磷 作用下， 以 氯仿 、 甲苯 为溶剂， 生成 4,7-Bis(5-bromothiophen-2-yl)-2-heptadecan-9-ylbenzotriazole
  参考文献：
  名称：

  Dopant-free, hole-transporting polymers containing benzotriazole acceptor unit for perovskite solar cells

  摘要：

  DOI：

  10.1016/j.dyepig.2022.110170
• 作为产物：
  描述：

  正辛基镁溴盐 在 偶氮二甲酸二异丙酯 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 3.0h， 生成 4,7-二溴-2-(9-十七烷基)-2H-苯并[1,2,3]三氮唑
  参考文献：
  名称：

  유기 반도체 화합물 및 제조방법과 이를 포함하는 유기전자소자

  摘要：

  本发明涉及有机半导体化合物、其制备方法以及包含该有机半导体化合物的有机电子器件，更详细地说，涉及包含奎诺萨林的有机半导体化合物、其制备方法以及包含该化合物的有机电子器件。此外，通过合成含硫基团的噻吩衍生物与奎诺萨林类化合物进行共聚，显示出较低的带隙，因此，包含该化合物的有机电子器件通过与本发明的有机半导体化合物和富勒烯衍生物作为光活性层的显著组合具有高效率。此外，由于本发明的有机半导体化合物具有高热稳定性和高溶解度，包含该化合物的有机电子器件具有优异的电学特性，因此，该有机电子器件特别适用于有机太阳能电池或有机薄膜晶体管的n-型材料。

  公开号：

  KR101495152B1
• 作为试剂：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 4,8-双(2-乙基己氧基)苯并 [1,2-b,4,5-b2]-二-噻吩 在 4,7-二溴-2-(9-十七烷基)-2H-苯并[1,2,3]三氮唑 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 、 水 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 49.0h， 生成 、
  参考文献：
  名称：

  Tin-Free Synthesis of a Ternary Random Copolymer for BHJ Solar Cells: Direct (Hetero)arylation versus Stille Polymerization

  摘要：

  In a recent report (Eur. J. Org. Chem. 2014, 30, 6583) we emphasized the importance of addressing research efforts in OPV-active materials toward synthetic processes scalable up to industrial production. In this context, palladium-catalyzed direct (hetero)arylation polymerization (DHAP) can be a suitable approach to reduce the number of reaction steps and to avoid the use of toxic reagents in the synthesis of donor polymers. Random donor acceptor copolymers have been shown to be promising materials for bulk heterojunction (BHJ) solar cells with high efficiencies and increased thermal stability. We report here the synthesis by DHAP of a ternary double-acceptor/donor random copolymer including benzo[c] [1,2,5]thiadiazole and benzo[d] [1,2,3]triazole as the accepting units and benzo[1,2-b;4,5-b']dithiophene as the donor moiety. The results are discussed in comparison with the synthesis of the same polymer via the Stifle polymerization. The coupling products formed in the early stage of the polycondensation have been isolated and characterized by NMR spectroscopy to gain insight into the regiochemistry of DHAP. The polymers synthesized have been tested in BHJ solar cells with PC,BM as the electron acceptor material. Power conversion efficiencies (up to 2.8%) are comparable or lower (depending on the processing conditions) than those of the same polymer synthesized via the Stille coupling reaction; however, the DHAP protocol is more convenient in terms of synthetic complexity.

  DOI：

  10.1021/acs.macromol.5b01676

文献信息

• Double acceptor D–A copolymers containing benzotriazole and benzothiadiazole units: chemical tailoring towards efficient photovoltaic properties
  作者：Dariusz Kotowski、Silvia Luzzati、Gabriele Bianchi、Anna Calabrese、Andrea Pellegrino、Riccardo Po、Giuliana Schimperna、Alessandra Tacca

  DOI：10.1039/c3ta11698k

  日期：——

  the design and synthesis of a series of D–A copolymers alternating benzothiadiazole and benzotriazole acceptors to a donor co-unit, and investigates their photovoltaic properties in bulk heterojunction solar cells with PC71BM. Successive modifications to the copolymers are carried out, passing from thiophene to benzodithiophene (BDT) donor co-units and from regular to random alternation of the accepting

  这项研究报告了一系列交替交替的D–A共聚物的设计和合成 苯并噻二唑 和 苯并三唑受体供体，并研究其在PC 71 BM的体异质结太阳能电池中的光伏性能。对共聚物进行了连续的改性，从噻吩苯并二噻吩（BDT）供体的联合单元，以及接受单元的常规或随机替代。在优化的设备中，包含噻吩共单元的共聚物的功率转换效率（PCE）为1.88％。从噻吩BDT的使用带来了一些优势，例如较低的光能隙和较低的光生电荷限制，这些都会积极影响到太阳辐射的光谱覆盖范围以及器件中的填充因子（FF）参数。从接受单元的规则分布到随机分布，BDT共聚物太阳能电池的PCE达到5％。这种令人鼓舞的光伏性能与高溶解度，高分子量和易于制备的过程相结合。这些特性是设想扩大到工业应用的必要条件。
• High-Performance Electron-Transporting Polymers Derived from a Heteroaryl Bis(trifluoroborate)
  作者：Jin-Kyun Lee、Michael C. Gwinner、Reinhard Berger、Carol Newby、Rudolf Zentel、Richard H. Friend、Henning Sirringhaus、Christopher K. Ober

  DOI：10.1021/ja201485p

  日期：2011.7.6

  In this communication, we report that dipotassium aryl bis(trifluoroborate)s make stable and easy-to-purify yet reactive monomers under Suzuki polycondensation reactions. A bis(trifluoroborate) of 2-alkylbenzotriazole was prepared successfully and copolymerized with dibromobenzothiadiazole in the presence of a Pd catalyst and LiOH, yielding high molecular weight conjugated polymers. This polymer (P1) composed of all electron-accepting units shows excellent electron-transport properties (mu(e) = 0.02 cm(2) V-1 s(-1)), which proves the value of the aryl bis(trifluoroborate) monomers and suggests that many other types of semiconducting polymers that could not be accessed previously can be synthesized using this approach.
• 유기 반도체 화합물 및 제조방법과 이를 포함하는 유기전자소자
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101495152B1

  公开（公告）日：2015-02-26

  본 발명은 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기전자소자에 관한 것으로, 보다 상세하게는 퀴녹살린을 포함하는 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기전자소자에 관한 것이다. 또한 황(S)을 포함하고 있는 티오펜 유도체를 합성하여 퀴녹살린계 화합물과 공중합하여 낮은 밴드갭을 나타내므로, 이를 포함하는 유기전자소자는 본 발명의 유기 반도체 화합물과 광활성층인 풀러렌 유도체와의 획기적인 조합으로 높은 효율을 가진다. 또한 본 발명의 유기 반도체 화합물은 높은 열적 안정성과 높은 용해도로 인해 이를 포함하는 유기전자소자는 우수한 전기특성을 가져 유기전자 소자 특히, 유기 태양전지 또는 유기박막트랜지스터의 n-type 재료로서 매우 유용하게 사용될 수 있다.

  本发明涉及有机半导体化合物、其制备方法以及包含该有机半导体化合物的有机电子器件，更详细地说，涉及包含奎诺萨林的有机半导体化合物、其制备方法以及包含该化合物的有机电子器件。此外，通过合成含硫基团的噻吩衍生物与奎诺萨林类化合物进行共聚，显示出较低的带隙，因此，包含该化合物的有机电子器件通过与本发明的有机半导体化合物和富勒烯衍生物作为光活性层的显著组合具有高效率。此外，由于本发明的有机半导体化合物具有高热稳定性和高溶解度，包含该化合物的有机电子器件具有优异的电学特性，因此，该有机电子器件特别适用于有机太阳能电池或有机薄膜晶体管的n-型材料。
• Dopant-free, hole-transporting polymers containing benzotriazole acceptor unit for perovskite solar cells
  作者：Jiabing Cao、Lijun Wang、Guofeng You、Lihua Li、Lu Yao、Zhonggao Zhou、E. Yang、Wanzhu Cai、Qidan Ling、Hongyu Zhen

  DOI：10.1016/j.dyepig.2022.110170

  日期：2022.4
• Tin-Free Synthesis of a Ternary Random Copolymer for BHJ Solar Cells: Direct (Hetero)arylation versus Stille Polymerization
  作者：G. Marzano、D. Kotowski、F. Babudri、R. Musio、A. Pellegrino、S. Luzzati、R. Po、G. M. Farinola

  DOI：10.1021/acs.macromol.5b01676

  日期：2015.10.13

  In a recent report (Eur. J. Org. Chem. 2014, 30, 6583) we emphasized the importance of addressing research efforts in OPV-active materials toward synthetic processes scalable up to industrial production. In this context, palladium-catalyzed direct (hetero)arylation polymerization (DHAP) can be a suitable approach to reduce the number of reaction steps and to avoid the use of toxic reagents in the synthesis of donor polymers. Random donor acceptor copolymers have been shown to be promising materials for bulk heterojunction (BHJ) solar cells with high efficiencies and increased thermal stability. We report here the synthesis by DHAP of a ternary double-acceptor/donor random copolymer including benzo[c] [1,2,5]thiadiazole and benzo[d] [1,2,3]triazole as the accepting units and benzo[1,2-b;4,5-b']dithiophene as the donor moiety. The results are discussed in comparison with the synthesis of the same polymer via the Stifle polymerization. The coupling products formed in the early stage of the polycondensation have been isolated and characterized by NMR spectroscopy to gain insight into the regiochemistry of DHAP. The polymers synthesized have been tested in BHJ solar cells with PC,BM as the electron acceptor material. Power conversion efficiencies (up to 2.8%) are comparable or lower (depending on the processing conditions) than those of the same polymer synthesized via the Stille coupling reaction; however, the DHAP protocol is more convenient in terms of synthetic complexity.