3-hexyl-5-(7-(4-hexylthiophene-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde | 1253948-64-9

• 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: 3-hexyl-5-(7-(4-hexylthiophene-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde
• 英文别名: 3-hexyl-5-(7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde；3-hexyl-5-(7-(4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)-thiophene-2-carbaldehyde；3-hexyl-5-(7-(4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde；[(3-hexylthiophen-2-yl)benzo[1,2,5]thiadiazol-4-yl]-4-hexylthiophene-2-carbaldehyde
• CAS: 1253948-64-9
• 化学式: C₂₇H₃₂N₂OS₃
• 分子量: 496.762
• InChiKey: DCHOHKSCGLKCCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.21
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42.85
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-hexyl-5-(7-(4-hexylthiophene-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde 在 三氯氧磷 作用下， 以 丙酸 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 [(4-hexylthiophen-5-formyl-2-yl)benzo[1,2,5]thiadiazol-4-yl]-4-hexylthiophene-2-10,15,20-tris(4-methylphenyl)porphyrin
  参考文献：
  名称：

  Porphyrins modified with a low-band-gap chromophore for dye-sensitized solar cells

  摘要：

  Two novel porphyrin dyes (PMBTZ and PHBTZ) modified with alkyl-thiophene and 2,1,3-benzothiadiazole (BTZ) moieties were designed and synthesized. The optical and electrochemical properties were characterized by UV-visible, fluorescence spectroscopy and cyclic voltammetry. With the introduction of the low-band-gap chromophore onto the porphyrins, the absorption spectra of the two porphyrin dyes in the range of 450-600 nm were broadened and the maximum wavelength was red-shifted compared with P-Zn as expected. The first oxidation potentials (E-ox1) were altered to the negative, which lowered from 1.27 to 1.11 and 1.15 eV, respectively. For a typical solar cell device based on dye PMBTZ, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to 65%, with a broad respondent region of 350-800 nm. Under standard global AM 1.5 solar condition, the dye-sensitized solar cell (DSSC) based on the dye PMBTZ showed the best photovoltaic performance: a short-circuit photocurrent density (J(sc)) of 14.11 mA/cm(2), an open-circuit photo voltage (V-oc) of 0.59 V, and a fill factor (ff) of 0.66, corresponding to solar-to-electric power conversion efficiency (eta) of 5.46%. (c) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.12.014
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 四(三苯基膦)钯 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 36.0h， 生成 3-hexyl-5-(7-(4-hexylthiophene-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  一种螺芴类衍生物及其制备方法和应用

  摘要：

  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。

  公开号：

  CN103087056B

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%。
• Development of a new benzo(1,2-b:4,5-b′)dithiophene-based copolymer with conjugated dithienylbenzothiadiazole–vinylene side chains for efficient solar cells
  作者：Zhaojie Gu、Ping Shen、Sai-Wing Tsang、Ye Tao、Bin Zhao、Peng Tang、Yujuan Nie、Yan Fang、Songting Tan

  DOI：10.1039/c1cc12851e

  日期：——

  A new benzodithiophene-based copolymer PTG1 with dithienylbenzothiadiazole-vinylene side chains exhibits excellent film-forming ability, a deep HOMO energy level, and a good miscibility with PC(71)BM. Bulk heterojunction polymer solar cells fabricated from PTG1 and PC(71)BM showed a promising power conversion efficiency over 4.0%.

  具有二噻吩基苯并噻二唑-亚乙烯基侧链的新型基于苯并二噻吩的共聚物PTG1表现出优异的成膜能力，较深的HOMO能级以及与PC（71）BM的良好混溶性。由PTG1和PC（71）BM制造的块状异质结聚合物太阳能电池显示出有希望的功率转换效率超过4.0％。
• 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
  作者：Zhao Hu、Xiao-dong Li、Wenjun Zhang、Aihui Liang、Dandan Ye、Zhitian Liu、Jing Liu、Yanjiao Liu、Junfeng Fang

  DOI：10.1039/c3ra44145h

  日期：——

  Two novel star-shaped donor–acceptor small molecules, TPA–TBT–CN and TPA–TBT–R, with triphenylamine (TPA) as the core, benzothiadiazole (BT) as the arm, and alkyl cyanoacetate or 3-ethylrhodanine as the end-group are synthesized for application as donor materials in OSCs. The two small molecule films show broad absorption bands from 300 nm to 850 nm, narrow optical band gaps (1.5–1.7 eV), deep HOMO energy levels (−5.0 to −5.1 eV) and moderate hole mobilities. OSCs based on blends of the two donors and PC70BM acceptors exhibit power conversion efficiencies of 1.34% and 1.79%, respectively. Notably, TPA–TBT–R with 3-ethylrhodanine as the end-group displays a broader solar spectral coverage, a lower HOMO level, a higher hole mobility and higher photovoltaic properties. Our results indicate that 3-ethylrhodanine as the acceptor and end-group is a promising linker in constructing donor materials for high efficiency OSCs.

  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。
• Synthesis and Photovoltaic Properties of Copolymers Based on Benzo[1,2-<i>b</i>:4,5-<i>b</i>′]dithiophene and Thiophene with Different Conjugated Side Groups
  作者：Zhaojie Gu、Peng Tang、Bin Zhao、Hao Luo、Xia Guo、Huajie Chen、Gui Yu、Xinping Liu、Ping Shen、Songting Tan

  DOI：10.1021/ma202399n

  日期：2012.3.13

  Three novel copolymers (PT-ID, PT-DTBT, and PT-DTBTID) of benzo[1,2-b:4,5-b′]dithiophene and thiophene with different conjugated side groups (1,3-indanedione (ID), 4,7-dithien-5-yl-2,1,3-benzodiathiazole (DTBT), and DTBT-ID) were synthesized and developed for polymer solar cell applications. The effects of the different conjugated side groups on the thermal, photophysical, electrochemical and photovoltaic

  苯并[1,2- b：4,5- b ']二噻吩和噻吩具有不同共轭侧基的三种新型共聚物（PT-ID，PT-DTBT和PT-DTBTID）（1,3-茚满二酮（ID） ，4,7-二噻吩-5-基-2,1,3-苯并二噻唑（DTBT）和DTBT-ID）合成并开发用于聚合物太阳能电池应用。研究了不同共轭侧基对这些共聚物的热，光物理，电化学和光伏性质的影响。随着共轭侧基长度的增加，溶液中UV-vis区域的吸收发生红移。通过改变不同的侧基，可以有效地调节所得共聚物的能级和带隙。这三种共聚物表现出较高的HOMO能级和相对较高的开路电压（V oc）。具有这些共聚物作为电子给体和（6,6）-苯基-C 61-丁酸甲酯（PC 61BM）作为电子受体对PT-ID，PT-DTBT和PT-DTBTID分别显示出2.48％，4.18％和1.16％的功率转换效率。
• 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