5-(7-(5-bromo-4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)-3-hexylthiophene-2-carbaldehyde | 1403579-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 5-(7-(5-bromo-4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)-3-hexylthiophene-2-carbaldehyde
• 英文别名: 5-(7-(5-bromo-4-hexylthiophene-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)-3-hexylthiophene-2-carbaldehyde；5-[4-(5-Bromo-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl]-3-hexylthiophene-2-carbaldehyde
• CAS: 1403579-44-1
• 化学式: C₂₇H₃₁BrN₂OS₃
• 分子量: 575.658
• InChiKey: LTVQIUCQDNQTFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(7-(5-bromo-4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)-3-hexylthiophene-2-carbaldehyde 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Functionalized Ruthenium Dialkynyl Complexes with High Second-Order Nonlinear Optical Properties and Good Potential as Dye Sensitizers for Solar Cells

  摘要：

  Various dipolar p-delocalized Ru(II) dialkynyl complexes were prepared and characterized. Their second-order nonlinear optical (NLO) properties were investigated by the electric-field-induced second harmonic generation (EFISH) technique working in CH2Cl2 solution with an incident wavelength of 1907 nm, whereas the dipole moments were determined by density functional theory (DFT) calculations. All the investigated complexes are characterized by a negative value of mu beta 1.907 EFISH, in agreement with a negative value of Delta mu eg (difference of the dipole moment in the excited and ground state) upon excitation. Their second-order NLO response can be easily modulated by the nature of the alkynyl substituents. Besides, the most promising pushpull ruthenium diacetylide complex, adequately functionalized for anchoring to TiO2, was tested as photosensitizer in dye-sensitized solar cells (DSSCs).

  DOI：

  10.1021/om5009378
• 作为产物：
  描述：

  3-己基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 27.25h， 生成 5-(7-(5-bromo-4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)-3-hexylthiophene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and photovoltaic properties of solution-processable star-shaped small molecules with triphenylamine as the core and alkyl cyanoacetate or 3-ethylrhodanine as the end-group

  摘要：

  以三苯胺（TPA）为核，苯并噻二唑（BT）为臂，氰乙酸烷基酯或 3-乙基罗丹宁为末端基团，合成了两种新型星形供体-受体小分子 TPA-TBT-CN 和 TPA-TBT-R，并将其用作 OSC 中的供体材料。这两种小分子薄膜显示出从 300 纳米到 850 纳米的宽吸收带、窄光带隙（1.5-1.7 eV）、深 HOMO 能级（-5.0 到 -5.1 eV）和适中的空穴迁移率。基于这两种给体和 PC70BM 受体混合物的 OSC 功率转换效率分别为 1.34% 和 1.79%。值得注意的是，以 3-ethylrhodanine 为端基的 TPA-TBT-R 显示出更宽的太阳光谱覆盖范围、更低的 HOMO 水平、更高的空穴迁移率和更高的光伏特性。我们的研究结果表明，3-乙基罗丹宁作为受体和末端基团是一种很有前途的连接体，可用于构建高效 OSC 的供体材料。

  DOI：

  10.1039/c3ra44145h

文献信息

• Synthesis and photovoltaic performances of conjugated copolymers with 4,7-dithien-5-yl-2,1,3-benzothiadiazole and di(p-tolyl)phenylamine side groups
  作者：Haohao Li、Hao Luo、Zhencai Cao、Zhaojie Gu、Ping Shen、Bin Zhao、Huajie Chen、Gui Yu、Songting Tan

  DOI：10.1039/c2jm33886f

  日期：——

  Three new copolymers (PT-TPA, PT-DTBT and PT-DTBTTPA) based on benzo[1,2-b:4,5-b]dithiophene (BDT) and thiophene with different conjugated side chains (di(p-tolyl)phenylamine (TPA), 4,7-dithien-5-yl-2,1,3-benzothiadiazole (DTBT) and DTBT-TPA) were synthesized via Stille coupling polymerization. The TPA and the DTBT were introduced to improve the hole-transport ability and broaden the absorption spectrum. The effects of different conjugated side groups on thermal, optical, electrochemical, hole-transporting and photovoltaic properties of these copolymers were investigated. Field effect results show that the copolymer PT-DTBTTPA containing TPA and DTBT in the side chain showed the highest hole mobility. The three copolymers exhibit deep-lying HOMO energy levels, which were effectively tuned by changing the side groups. Photovoltaic cells were fabricated with the synthesized copolymers as electron donors and [6,6]-phenyl-C-butyric acid methyl ester (PCBM) as the electron acceptor. Bulk heterojunction polymer solar cells based on PT-DTBT and PT-DTBTTPA showed promising power conversion efficiencies of 5.50% and 5.16%, respectively.

  三种新型共聚合物（PT-TPA、PT-DTBT和PT-DTBTTPA）基于苯并[1,2-b:4,5-b]二硫噻吩（BDT）和不同的共轭侧链（对甲基苯基胺（TPA）、4,7-二噻吩-5-基-2,1,3-苯并噻唑（DTBT）和DTBT-TPA）通过斯蒂尔耦合聚合反应合成。引入TPA和DTBT是为了改善载流子传输能力并拓宽吸收光谱。研究了不同共轭侧基对这些共聚合物的热、电光、电子化学、载流子传输及光伏性能的影响。场效应结果表明，侧链中含有TPA和DTBT的共聚合物PT-DTBTTPA展现出最高的孔迁移率。这三种共聚合物具有较深的HOMO能级，通过改变侧基有效调节。采用合成的共聚合物作为电子供体，以[6,6]-苯基-C-丁酸甲酯（PCBM）作为电子受体制作了光伏电池。基于PT-DTBT和PT-DTBTTPA的薄膜异质结聚合物太阳能电池分别显示出有前景的光电转换效率，达到5.50%和5.16%。
• 一种螺芴类衍生物及其制备方法和应用
  申请人：中国科学院宁波材料技术与工程研究所

  公开号：CN103087056B

  公开（公告）日：2016-02-03

  本发明公开了一种螺芴类衍生物，其结构如式(I)所示；式(I)中，R1、R2、R3和R4为端基受体基团，独立地选自如式(I-a)、式(I-b)或式(I-c)所示的基团。该螺芴类衍生物对可见光的吸收能力强，可以作为一种小分子给体材料应用于有机太阳能领域。本发明还公开了螺芴类衍生物的制备方法，以4，7-二溴苯并噻二唑和4-己基-2-三丁基锡噻吩为起始原料，依次经过Stille偶联反应、维尔斯迈尔-哈克反应、溴代反应、Suzuki偶联反应和费纳格尔缩合反应得到螺芴类衍生物。
• Synthesis and photovoltaic properties of conjugated side chains polymers with different electron-withdrawing and donating end groups
  作者：Zhaojie Gu、Lijun Deng、Hao Luo、Xia Guo、Haohao Li、Zhencai Cao、Xunshan Liu、Xinwei Li、Hongyan Huang、Yingzi Tan、Yong Pei、Songting Tan

  DOI：10.1002/pola.26180

  日期：2012.9.15

  thermal stability. These conjugated polymers show the broad ultraviolet‐visible absorption and the narrow optical band gaps in the range of 1.65–1.90 eV. Through changing the end group of conjugated side chains, the photophysical properties and energy levels of the polymers were tuned effectively. Bulk heterojunction solar cells based on the blend of these polymers and (6,6)‐phenyl‐C61‐butyric acid methyl

  一系列新颖的低带隙聚合物，含有与4,7-二噻吩-5-基-2,1,3-苯并二噻唑共轭的侧链和不同的醛吸电子端基（PT-DTBTCHO），氰基乙酸2-乙基己酯（PT-DTBTCN），1,3-二乙基-2-硫代巴比妥酸（PT-DTBTDT）和2-甲基噻吩的供电子端基（PT-DTBTMT）已被设计和合成。所有聚合物在普通有机溶剂中均显示出良好的溶解性，成膜能力和热稳定性。这些共轭聚合物在1.65–1.90 eV的范围内显示出广泛的紫外可见吸收和窄的光学带隙。通过改变共轭侧链的端基，可以有效地调节聚合物的光物理性质和能级。基于这些聚合物和（6,6）-苯基-C 61-丁酸甲酯（PC 61 BM）的混合物的体异质结太阳能电池达到了2.72％的最佳功率转换效率（PCE）。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年
• Rigid triarylamine-based D–A–π–A structural organic sensitizers for solar cells: the significant enhancement of open-circuit photovoltage with a long alkyl group
  作者：Xiaohao Hu、Shengyun Cai、Guojian Tian、Xin Li、Jianhua Su、Jing Li

  DOI：10.1039/c3ra43057j

  日期：——

  Five new organic D–A–π–A sensitizers DIA6–DIA10 containing benzothiadiazole (BTD) or benzotriazole (BTZ) as auxiliary electron withdrawing units have been synthesized. Their photophysical, electrochemical and photovoltaic properties have been studied. Consequently, although all of these dyes have long alkyl chains grafted on a π-bridge, DSSCs with dyes containing a BTZ unit displayed higher open circuit voltages (757–829 mV) than those containing a BTD unit (682–712 mV). This may be because the nitrogen-based heterocyclic group of BTZ can lift the conduction band edge and reduce the charge recombination that arises from the absence of the sulfur atom. Benefiting from this and the introduction of alkyl chains on the nitrogen atom, DSSCs with one dye containing BTZ and thieno[3,2-b]thiophene (TT) as the π-spacer (DIA7) showed the highest open circuit voltage (Voc = 829 mV). The addition of one more thiophene unit to DIA6 broadens the absorption spectra, leading the DIA8 device to produce the largest photocurrent. Among these sensitizers, the best photovoltaic performance was obtained by the DIA8 device, with a short circuit photocurrent density (Jsc) of 13.45 mA cm−2, an open-circuit photovoltage (Voc) of 757 mV, and a fill factor (FF) of 70%, corresponding to an overall conversion efficiency (η) of 7.15% which reached 93% of the reference dye N719-based cell under standard global AM 1.5 solar light conditions.

  我们合成了五种新的有机 DâAâÏâA敏化剂 DIA6âDIA10 ，它们含有作为辅助取电子单元的苯并噻二唑（BTD）或苯并三唑（BTZ）。对它们的光物理、电化学和光伏特性进行了研究。结果表明，尽管所有这些染料都具有接枝在Ï桥上的长烷基链，但含有 BTZ 单元的染料的 DSSC 的开路电压（757â829 mV）高于含有 BTD 单元的 DSSC 的开路电压（682â712 mV）。这可能是因为 BTZ 的氮基杂环基团可以提升导带边缘，减少因硫原子缺失而产生的电荷重组。得益于这一点以及在氮原子上引入烷基链，使用一种含有 BTZ 和噻吩并[3,2-b]噻吩（TT）作为Ï-间隔物的染料的 DSSC（DIA7）显示出最高的开路电压（Voc = 829 mV）。在 DIA6 中增加一个噻吩单元可拓宽吸收光谱，从而使 DIA8 器件产生最大的光电流。在这些敏化剂中，DIA8 器件的光电性能最好，其短路光电流密度（Jsc）为 13.45 mA cmâ2，开路光电电压（Voc）为 757 mV，填充因子（FF）为 70%，总转换效率（δ-）为 7.15%，在全球 AM 1.5 标准太阳光条件下达到了基于 N719 参考染料电池的 93%。