1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde N-(4-formyl)phenyl-N-phenylhydrazone | 1529853-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde N-(4-formyl)phenyl-N-phenylhydrazone
• 英文别名: 4-(N-[(1-phenyl-3-propoxy-3,4-dihydro-2H-quinolin-6-yl)methylideneamino]anilino)benzaldehyde
• CAS: 1529853-62-0
• 化学式: C₃₂H₃₁N₃O₂
• 分子量: 489.617
• InChiKey: RHPDKGFTFXLRGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  674.5±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde N-(4-formyl)phenyl-N-phenylhydrazone 、 氰乙酸 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以66.7%的产率得到2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid
  参考文献：
  名称：

  A structural study of 1-phenyl-1,2,3,4-tetrahydroquinoline-based dyes for solid-state DSSC applications

  摘要：

  D-pi-A architecture metal-free organic dyes, with a tetrahydroquinoline unit as electron donor, were designed and synthesized for solid-state dye-sensitized solar cells. The sensitizer series was designed to develop a structure-property relationship. These dyes are obtained from relatively cheap starting materials, without the use of expensive catalysts, rigorously anhydrous or oxygen-free conditions. The highest solid-state device conversion efficiency (eta) 33% (J(SC) = -5.9 mA cm(-2), V-OC = 780 mV) and fill factor FF = 0.72 under 100 mW cm(-2) (AM 1.5G) solar irradiation was achieved with dye D4 employing a hydrazone fragment as the spacer between the donor 3-alkoxy-1-phenyl-1,2,3,4-tetrahydroquinoline and the rhodanine acceptor of the sensitizer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.01.010
• 作为产物：
  描述：

  3-acetyl-1-phenyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde 在 potassium carbonate 、 sodium sulfate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 6.58h， 生成 1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde N-(4-formyl)phenyl-N-phenylhydrazone
  参考文献：
  名称：

  A structural study of 1-phenyl-1,2,3,4-tetrahydroquinoline-based dyes for solid-state DSSC applications

  摘要：

  D-pi-A architecture metal-free organic dyes, with a tetrahydroquinoline unit as electron donor, were designed and synthesized for solid-state dye-sensitized solar cells. The sensitizer series was designed to develop a structure-property relationship. These dyes are obtained from relatively cheap starting materials, without the use of expensive catalysts, rigorously anhydrous or oxygen-free conditions. The highest solid-state device conversion efficiency (eta) 33% (J(SC) = -5.9 mA cm(-2), V-OC = 780 mV) and fill factor FF = 0.72 under 100 mW cm(-2) (AM 1.5G) solar irradiation was achieved with dye D4 employing a hydrazone fragment as the spacer between the donor 3-alkoxy-1-phenyl-1,2,3,4-tetrahydroquinoline and the rhodanine acceptor of the sensitizer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.01.010

文献信息

• Organic dyes comprising a hydrazone moiety and their use in dye-sensitized solar cells
  申请人：BASF SE

  公开号：US09831042B2

  公开（公告）日：2017-11-28

  The present invention relates to compounds of general formula I wherein R100 and R200 are each independently hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C7-cycloalkyl, aryl, aryl-C1-C10-alkyl or aryloxy-C1-C10-alkyl, D is an m-valent (m=1, 2 or 3) donor moiety which comprises at least one carbon-carbon or carbon-heteroatom double bond and/or at least one unfused or fused carbo- or heterocyclic ring, A is an acceptor moiety which comprises at least one carbon-carbon or carbon-heteroatom double bond and/or at least one unfused or fused carbo- or heterocyclic ring, and the donor moiety D and the acceptor moiety A are π-conjugated to one another. Furthermore, the present invention relates to the use of compounds of formula I for producing dye-sensitized solar cells and to dye-sensitized solar cells comprising compounds of formula I.

  本发明涉及一般式I的化合物，其中R100和R200各自独立地为氢、C1-C10烷基，其中在C2烷基的情况下可能被一个，而在C3-C10烷基的情况下可能被一个或两个不相邻的氧原子所打断，C5-C7环烷基，芳基，芳基-C1-C10烷基或芳氧基-C1-C10烷基，D是一个m价（m=1、2或3）供体基团，其中包括至少一个碳-碳或碳-杂原子双键和/或至少一个未融合或融合的碳或杂环状环，A是一个受体基团，其中包括至少一个碳-碳或碳-杂原子双键和/或至少一个未融合或融合的碳或杂环状环，供体基团D和受体基团A彼此π共轭。此外，本发明涉及使用式I的化合物制备染料敏化太阳能电池，并包括式I的化合物的染料敏化太阳能电池。
• ヒドラゾン部分を含有する有機色素及びそれらの色素増感太陽電池における使用
  申请人：ビーエーエスエフ ソシエタス・ヨーロピアＢＡＳＦ ＳＥ

  公开号：JP2015528836A

  公开（公告）日：2015-10-01

  一般式（Ｉ）の化合物、色素増感太陽電池を製造するためのその使用、及び式（Ｉ）の化合物を含む色素増感太陽電池に関する。

  这句话的中文翻译是： 涉及一般式（I）的化合物、用于制造染料敏化太阳能电池的颜料增感剂、以及包含一般式（I）的化合物的染料敏化太阳能电池。
• A structural study of 1-phenyl-1,2,3,4-tetrahydroquinoline-based dyes for solid-state DSSC applications
  作者：Kasparas Rakstys、Joana Solovjova、Tadas Malinauskas、Ingmar Bruder、Robert Send、Algirdas Sackus、Rüdiger Sens、Vytautas Getautis

  DOI：10.1016/j.dyepig.2014.01.010

  日期：2014.5

  D-pi-A architecture metal-free organic dyes, with a tetrahydroquinoline unit as electron donor, were designed and synthesized for solid-state dye-sensitized solar cells. The sensitizer series was designed to develop a structure-property relationship. These dyes are obtained from relatively cheap starting materials, without the use of expensive catalysts, rigorously anhydrous or oxygen-free conditions. The highest solid-state device conversion efficiency (eta) 33% (J(SC) = -5.9 mA cm(-2), V-OC = 780 mV) and fill factor FF = 0.72 under 100 mW cm(-2) (AM 1.5G) solar irradiation was achieved with dye D4 employing a hydrazone fragment as the spacer between the donor 3-alkoxy-1-phenyl-1,2,3,4-tetrahydroquinoline and the rhodanine acceptor of the sensitizer. (C) 2014 Elsevier Ltd. All rights reserved.