3-ethoxy-4-[(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-3-cyclobutene-1,2-dione | 189811-20-9

• 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: 3-ethoxy-4-[(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-3-cyclobutene-1,2-dione
• 英文别名: (E)-3-ethoxy-4-((1-ethyl-3,3-dimethylindolin-2-ylidene)methyl)cyclobut-3-ene-1,2-dione；3-ethoxy-4-[(E)-(1-ethyl-3,3-dimethylindol-2-ylidene)methyl]cyclobut-3-ene-1,2-dione
• CAS: 189811-20-9
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: YTJKLAALNFYPFI-RVDMUPIBSA-N

物化性质

• 沸点：
  420.5±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethoxy-4-[(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-3-cyclobutene-1,2-dione 在 sodium hydroxide 作用下， 以 乙醇 、 正丁醇 、 苯 为溶剂， 反应 18.08h， 生成 5-carboxy-2-[[3-[(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-trimethyl-1-octyl-3H-indolium
  参考文献：
  名称：

  Efficient Far Red Sensitization of Nanocrystalline TiO₂ Films by an Unsymmetrical Squaraine Dye

  摘要：

  An asymmetric squaraine sensitizer comprising an anchoring group was engineered at the molecular level and synthesized. The functionalized novel squaraine sensitizers upon anchoring onto a TiO2 film exhibit an unprecedented incident photon to current conversion efficiency of 85%. The photovoltaic data of this sensitizer using an electrolyte having composition of 0.6 M M-methyl-N-butyl imidazolium iodide, 0.05 M iodine, 0.1 M LiI, 0.05 M tert-butylpyridine in a 15/85 (v/v) mixture of valeronitrile and acetonitrile revealed a short circuit photocurrent density of 10.5 +/- 0.2 mA/cm(2), an open circuit voltage of 603 +/- 10 mV, and a fill factor of 0.71 +/- 0.02, corresponding to an overall conversion efficiency of 4.50% under standard AM 1.5 sunlight.

  DOI：

  10.1021/ja0731470
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 54.0h， 生成 3-ethoxy-4-[(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Bright fluorogenic squaraines with tuned cell entry for selective imaging of plasma membrane vs. endoplasmic reticulum

  摘要：

  一种理性设计的两性苝染料调节细胞进入，实现在1纳摩尔探针浓度下选择性远红外/近红外成像细胞膜vs.内质网。

  DOI：

  10.1039/c5cc06094j

文献信息

• A Near-Infrared<i>cis</i>-Configured Squaraine Co-Sensitizer for High-Efficiency Dye-Sensitized Solar Cells
  作者：Chuanjiang Qin、Youhei Numata、Shufang Zhang、Ashraful Islam、Xudong Yang、Keitaro Sodeyama、Yoshitaka Tateyama、Liyuan Han

  DOI：10.1002/adfm.201203384

  日期：2013.8.12

  AbstractA cis‐configured squaraine dye (HSQ1), synthesized by incorporation of a strongly electron‐withdrawing dicyanovinyl group into the central squaric acid moiety, is employed in dye‐sensitized solar cells (DSCs). In solution, HSQ1 displays an intense absorption in the near‐infrared region with a maximum at 686 nm and when the dye is adsorbed on a TiO2 surface, the absorption spectrum broadens in both the blue and the near‐infrared regions, which is favorable for efficient light harvesting over a broad wavelength range. A solar cell sensitized with HSQ1 shows a broader incident photon‐to‐current conversion efficiency (IPCE) spectrum (from 400 to 800 nm) and a higher IPCE in the long‐wavelength region (71% at 700 nm) than a cell sensitized with squaraine dye SQ1. Furthermore, a solar cell co‐sensitized with HSQ1 and N3 dye shows remarkably improved short‐circuit current density and open‐circuit voltage compared to those of a DSC based on N3 alone and fabricated under the same conditions. The energy‐conversion efficiency of the co‐sensitized DSC is 8.14%, which is the highest reported efficiency for a squaraine dye–based co‐sensitized DSC without using Al2O3 layer.