3,6-bis(2-bromo-3-hexylthiophen-5-yl)-1,2,4,5-tetrazine | 1246675-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3,6-bis(2-bromo-3-hexylthiophen-5-yl)-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(5-bromo-4-hexyl-2-thienyl)-1,2,4,5-tetrazine；3,6-Bis(5-bromo-4-hexylthiophen-2-yl)-1,2,4,5-tetrazine；3,6-bis(5-bromo-4-hexylthiophen-2-yl)-1,2,4,5-tetrazine
• CAS: 1246675-53-5
• 化学式: C₂₂H₂₈Br₂N₄S₂
• 分子量: 572.431
• InChiKey: VUTQEANNTJYSHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-bis(2-bromo-3-hexylthiophen-5-yl)-1,2,4,5-tetrazine 、 tributyl(4-(2-octyldodecyl)thiophen-2-yl)stannane 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以86.8%的产率得到3,6-bis(3-hexyl-4'-(2-octyldodecyl)-[2,2′-bithiophen]-5-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Development of s-tetrazine-based polymers for efficient polymer solar cells by controlling appropriate molecular aggregation

  摘要：

  Two conjugated polymers PTTTz and PHTTz have been designed and synthesized by introducing s-tetrazine as electron-withdrawing moieties. Compared with PTTTz with 2-octyldodecyl-substituted tetrathiophene derivative as electron-donating moieties, PHTTz with hexyl- and 2-octyldodecyl-substituted hexathiophene derivative possesses relatively lower molecular coplanarity, larger stacking distance but more orderly molecular stacking, more red-shifted absorption, more suitable microphase separation, more efficient exciton dissociation, higher hole mobility, which lead to higher short-circuit current density (11.54 mA cm(-2)), fill factor (69.0%) and power conversion efficiency (PCE = 6.69%) values in PSCs. The PITTz-based PSC shows an open circuit voltage of 1.02 V for its lower-ling HOMO energy level though the PCE of the PSC is only 5.16%. Moreover, the ternary PSC based PHITz/PC71BM/ITIC exhibits a higher PCE value of 7.88% than the binary PSCs for more efficient exciton dissociation and complementary absorption spectrum in ternary blend film, which is one of the highest PCE values in s-tetrazine-based polymers.

  DOI：

  10.1016/j.dyepig.2019.107717
• 作为产物：
  描述：

  4-己基噻吩-2-甲醛 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 potassium acetate 、 sulfur 、 一水合肼 、 溶剂黄146 、 亚硝酸异戊酯 作用下， 以 乙醇 、 氯仿 、 乙酸酐 为溶剂， 生成 3,6-bis(2-bromo-3-hexylthiophen-5-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  用于有机光伏应用的二噻吩基-s-四嗪和环戊二噻吩的交替共聚物

  摘要：

  作为新兴的缺乏电子的新组成部分，s-四嗪（Tz）具有很高的电子亲和力，甚至比常用的苯并噻二唑单元还要高。这种特性使Tz成为低带隙共轭聚合物，特别是有机太阳能电池材料非常有希望的吸电子单元。我们报告的合成和性质的五个交替共聚物的s-四嗪和环戊[2,1-b：3,4-b']二噻吩（CPDT），这是一个噻吩单元桥接。将甲基，己基和/或2-乙基己基引入到噻吩和CPDT单元上，以调节所得聚合物的溶解度，紫外线吸收，前沿分子轨道能级和链间堆积特性。这些聚合物可在高达220°C的温度下保持稳定，并在较高的温度下分解为Tz键，从而分解为二腈化合物。71-丁酸甲基酯（PC 71 BM），在模拟的1.5 m AM / 100 GW / cm 2的AM辐照下，它们的功率转换效率高达5.53％。然后通过原子力显微镜（AFM）分析来自不同聚合物或在不同加工条件下的活性层的形态结构，并将其与器件性能相关联。

  DOI：

  10.1021/cm200330c

文献信息

• TETRAZINE MONOMERS AND COPOLYMERS FOR USE IN ORGANIC ELECTRONIC DEVICES
  申请人：DING Jianfu

  公开号：US20120007026A1

  公开（公告）日：2012-01-12

  Copolymers of formula (I): where each A is S, Se or C═C; each x is an integer from 1 to 4; each R1 is independently H, F, CN or a C 1 -C 20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, n is an integer 5 or greater, can be formed into films or membranes that are useful as active layers in organic electronic device, such as PV solar cells, providing high power conversion efficiencies and good thermal stability. Such copolymers may be synthesized from monomers of formula (II): by Stille or Suzuki coupling reactions. Such monomers may be synthesized by a variation of the Pinner synthesis.

  公式（I）的共聚物：其中每个A是S、Se或C═C；每个x是从1到4的整数；每个R1独立地是H、F、CN或C1-C20线性或支链脂肪族基团；Ar是一个或多个取代或未取代的芳香族单元；n是一个大于或等于5的整数，可以形成用作有机电子器件中的活性层的薄膜或膜，例如PV太阳能电池，提供高功率转换效率和良好的热稳定性。这种共聚物可以通过Stille或Suzuki偶联反应从公式（II）的单体合成。这种单体可以通过Pinner合成的变体合成。
• Development of a New s-Tetrazine-Based Copolymer for Efficient Solar Cells
  作者：Zhao Li、Jianfu Ding、Naiheng Song、Jianping Lu、Ye Tao

  DOI：10.1021/ja106052e

  日期：2010.9.29

  A new s-tetrazine-based low-bandgap semiconducting polymer, PCPDTTTz, was designed and synthesized. This is the first solution-processable conjugated polymer with tetrazine in the main chain. This polymer shows good thermal stability and broad absorption covering 450-700 nm. The HOMO and LUMO energy levels were estimated to be -5.34 and -3.48 eV, with an electrochemical bandgap of 1.86 eV. Simple polymer solar cells based on PCPDTTTz and PC71BM exhibit a calibrated power conversion efficiency of 5.4%.
• Donor–acceptor copolymers incorporating polybenzo[1,2-b:4,5-b′]dithiophene and tetrazine for high open circuit voltage polymer solar cells
  作者：Weidong Cheng、Zhenghui Wu、Shanpeng Wen、Bin Xu、Hui Li、Furong Zhu、Wenjing Tian

  DOI：10.1016/j.orgel.2013.05.015

  日期：2013.9

  Two new low band gap conjugated polymers containing a benzo[1,2-b: 4,5-b'] dithiophene donor unit and a tetrazine acceptor unit were synthesized by Stille cross-coupling polymerization. The structural and thermal properties of copolymers were characterized using nuclear magnetic resonance, gel permeation chromatography and thermogravimetric analysis. The results show that the donor-acceptor copolymers thus developed have good thermal stability with decomposition temperature of 294 degrees C and 305 degrees C. Cyclic voltammetric study revealed that the copolymers possess a deep-lying highest occupied molecular orbital energy level, which is desired for high open circuit voltage polymer solar cells (PSCs) and is also favorable for stable device operation in air. Bulk-heterojunction PSCs based on blend of low band gap copolymers: [6,6]-phenyl-C71-butyric acid methyl ester on indium tin oxide/glass substrates were fabricated. This work yielded a promising power conversion efficiency of >5.0%, with a high open circuit voltage of similar to 1.0 V, measured under air mass 1.5 global irradiation of 100 mW/cm(2). Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.
• US8673183B2
  申请人：——

  公开号：US8673183B2

  公开（公告）日：2014-03-18
• Alternating Copolymers of Dithienyl-s-Tetrazine and Cyclopentadithiophene for Organic Photovoltaic Applications
  作者：Zhao Li、Jianfu Ding、Naiheng Song、Xiaomei Du、Jiayun Zhou、Jianping Lu、Ye Tao

  DOI：10.1021/cm200330c

  日期：2011.4.12

  frontier molecular orbital energy levels, and interchain stacking property of the resulting polymers. These polymers are stable up to 220 °C and decompose to dinitrile compounds with the breaking of Tz linkage at a higher temperature. Efficient bulk heterojunction solar cells were fabricated by blending these polymers with (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM), and they reached a power conversion

  作为新兴的缺乏电子的新组成部分，s-四嗪（Tz）具有很高的电子亲和力，甚至比常用的苯并噻二唑单元还要高。这种特性使Tz成为低带隙共轭聚合物，特别是有机太阳能电池材料非常有希望的吸电子单元。我们报告的合成和性质的五个交替共聚物的s-四嗪和环戊[2,1-b：3,4-b']二噻吩（CPDT），这是一个噻吩单元桥接。将甲基，己基和/或2-乙基己基引入到噻吩和CPDT单元上，以调节所得聚合物的溶解度，紫外线吸收，前沿分子轨道能级和链间堆积特性。这些聚合物可在高达220°C的温度下保持稳定，并在较高的温度下分解为Tz键，从而分解为二腈化合物。71-丁酸甲基酯（PC 71 BM），在模拟的1.5 m AM / 100 GW / cm 2的AM辐照下，它们的功率转换效率高达5.53％。然后通过原子力显微镜（AFM）分析来自不同聚合物或在不同加工条件下的活性层的形态结构，并将其与器件性能相关联。