5,5'-(9-hexyl-9H-carbazole-3,6-diyl)dithiophene-2-carbaldehyde | 1383124-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,5'-(9-hexyl-9H-carbazole-3,6-diyl)dithiophene-2-carbaldehyde
• 英文别名: 5,5’-(9-hexyl-9H-carbazole-3,6-diyl)bis(thiophene-2-carbaldehyde)；3,6-bis(5-formylthiophene-2-yl)-9-hexyl-9H-carbazole；5-[6-(5-Formylthiophen-2-yl)-9-hexylcarbazol-3-yl]thiophene-2-carbaldehyde
• CAS: 1383124-67-1
• 化学式: C₂₈H₂₅NO₂S₂
• 分子量: 471.644
• InChiKey: UVBRNCXNMGQMEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羧甲基绕丹宁 、 5,5'-(9-hexyl-9H-carbazole-3,6-diyl)dithiophene-2-carbaldehyde 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 以86%的产率得到2,2'-((((9-hexyl-9H-carbazole-3,6-diyl)bis(thiophene-5,2-diyl))bis(methaneylylidene))bis(4-oxo-2-thioxothiazolidin-3-yl-5-ylidene))diacetic acid
  参考文献：
  名称：

  Synthesis and Photovoltaic Performance of Long Wavelength Absorbing Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  We prepared novel organic photo-sensitizers based on a carbazole framework containing various acceptors with thiophene bridge units in the chromophore for the application to dye-sensitized solar cell (DSSC). Furthermore, organic dyes without bridge in the chromophore also synthesized to investigate the correlation between conjugation lengths and photon-to-current efficiency (PCE). Compared to non-bridged dyes, the DSSCs device containing multi-anchoring dyes with thiophene bridge exhibited much higher PCEs, resulting from efficient electron extraction pathways, higher molar extinction coefficients, and better light absorption in longer wavelengths.

  DOI：

  10.1080/15421406.2011.601189
• 作为产物：
  描述：

  溴己烷 在 N-溴代丁二酰亚胺(NBS) 、 trans-bis(triphenylphosphine)palladium dichloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 21.0h， 生成 5,5'-(9-hexyl-9H-carbazole-3,6-diyl)dithiophene-2-carbaldehyde
  参考文献：
  名称：

  基于咔唑和红色吸收性阳离子吲哚的单支和双支有机染料用于p型染料敏化太阳能电池：结合实验和理论研究

  摘要：

  已经为p型染料敏化太阳能电池合成了一系列新颖的单支和双支咔唑基红色吸收阳离子染料，不含（CSI和CDI），不含（CST和CDT）噻吩间隔基（p-DSSC）。吸收红光的阳离子受体/噻吩间隔基的引入导致吸收最大值从CSI的600 nm起始到CDT的800 nm扩展和红移，并提高了摩尔吸收率。双支/噻吩间隔基的引入降低了CDI，CST和CDT的最低空位分子轨道（LUMO）水平，使其电势比CSI更强。其中，双支CDI的转化效率最高，为0.112％。此外，在相似的制造条件下测得的所有染料均优于标准C343染料（0.062％）。尽管由于噻吩间隔基的引入导致光伏性能下降，但总体而言，与单支链染料的SC和V OC值相比。电化学阻抗谱分析表明，双支化染料比单支化染料具有更低的电荷转移电阻和更长的空穴寿命。进行密度泛函理论（DFT）和与时间有关的DFT计算，以从理论上表征合成染料的光学和电化学性质。

  DOI：

  10.1016/j.dyepig.2017.09.042

文献信息

• Metal-free organic luminophores with ultrastrong dipole moment exhibiting force-induced near-infrared emission (>800 nm) turn-on
  作者：Jie Li、Jingjuan Xie、Rong Zhang、Shiwen Guo、Fang Zhang、Kunpeng Guo、Shaohua Dong

  DOI：10.1039/c8cc05616a

  日期：——

  We demonstrated metal-free organic luminophores with ultrastrong dipole moment up to 22.7 Debye, and they exhibited emission turn-on peaks at 822 nm upon grinding.

  我们展示了具有极强偶极矩（高达22.7 Debye）的无金属有机荧光体，它们在研磨时表现出发射开启峰值为822纳米。
• Carbazole based A-π-D-π-A dyes with double electron acceptor for dye-sensitized solar cell
  作者：K.S.V. Gupta、Thogiti Suresh、Surya Prakash Singh、Ashraful Islam、Liyuan Han、Malapaka Chandrasekharam

  DOI：10.1016/j.orgel.2013.11.020

  日期：2014.1

  Three novel carbazole-based A-pi-D-pi-A-featured dyes (CSG1-CSG3) have been designed, synthesized for applications in dye-sensitized solar cells and fully characterized with NMR, MS, IR, UV-vis and electrochemical measurements. These dyes share the same donor (N-hexylcarbazole) and acceptor/anchoring group (cyanoacrylic acid), but differs in conjugated linkers incorporated, such as benzene, furan or thiophene, to configure the novel A-pi-D-pi-A framework for effective electron flow. The power conversion efficiencies were observed to be sensitive to the p-bridging linker moiety. The photovoltaic experiments showed that dye with a benzene linker exhibited a higher open-circuit voltage (0.699 V) compared to thiophene and furan linker. Among all dyes, CSG2 containing a thiophene linker exhibited the maximum overall conversion efficiency of 3.8% (J(SC) = 8.90 mA cm (2), V-OC = 584 mV, FF = 0.74) under standard global AM 1.5 G solar condition. Under similar fabrication conditions, champion dye N719 exhibited the maximum overall conversion efficiency of 6.4% (J(SC) = 14.74 mA cm (2), V-OC = 606 mV, FF = 0.716). (C) 2013 Elsevier B.V. All rights reserved.