5-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-thiophene-2-carbaldehyde | 922737-37-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-thiophene-2-carbaldehyde
• 英文别名: 5-[4-[Bis(9,9-dimethylfluoren-2-yl)amino]phenyl]thiophene-2-carbaldehyde
• CAS: 922737-37-9
• 化学式: C₄₁H₃₃NOS
• 分子量: 587.785
• InChiKey: LGHIUYQHNXUKQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-thiophene-2-carbaldehyde 在 哌啶 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 5-{5-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-thiophen-2-yl}-2-cyanopenta-2,4-dienoic acid
  参考文献：
  名称：

  Novel conjugated organic dyes containing bis-dimethylfluorenyl amino phenyl thiophene for efficient solar cell

  摘要：

  Two novel organic dyes (JK- 5 and JK- 6) containing bis-dimethylfluorenyl amino phenyl thiophene and additional methine unit are synthesized. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using these dyes. A solar-to-electric conversion efficiency of 5.12% and 4.78% is achieved with JK- 5 and JK- 6, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.061
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 N,N-bis(9,9-dimethylfluorenyl)-4-(2-thienyl)aniline 在 三氯氧磷 作用下， 以81%的产率得到5-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-thiophene-2-carbaldehyde
  参考文献：
  名称：

  用于太阳能电池应用的有机敏化剂的分子工程

  摘要：

  在分子水平上设计并合成了包含供体、电子传导和锚定基团的新型有机敏化剂。功能化的不对称有机敏化剂 3-{5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) 和 3 -{5'-[N,N-双(9,9-二甲基芴-2-基)苯基]-2,2'-双噻吩-5-基}-2-氰基-丙烯酸(JK-2)，在锚定在 TiO2 薄膜上，表现出前所未有的入射光子电流转换效率为 91%。使用含有 0.6 M-甲基-N-丁基咪唑鎓碘化物、0.04 M 碘、0.025 M LiI、0.05 M 硫氰酸胍和 0.28 M 叔丁基吡啶的 15/85 (v/v) 电解液的光伏数据戊腈和乙腈的混合物显示短路光电流密度为 14.0 +/- 0.2 mA/cm2，753 +/- 10 mV 的开路电压和 0.76 +/-

  DOI：

  10.1021/ja066376f

文献信息

• Molecular Engineering of Organic Sensitizers for Solar Cell Applications
  作者：Sanghoon Kim、Jae Kwan Lee、Sang Ook Kang、Jaejung Ko、J.-H. Yum、Simona Fantacci、Filippo De Angelis、D. Di Censo、Md. K. Nazeeruddin、Michael Grätzel

  DOI：10.1021/ja066376f

  日期：2006.12.1

  Novel organic sensitizers comprising donor, electron-conducting, and anchoring groups were engineered at molecular level and synthesized. The functionalized unsymmetrical organic sensitizers 3-5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) and 3-5'-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-2,2'-bisthiophene-5-yl}-2-cyano-acrylic acid (JK-2), upon anchoring

  在分子水平上设计并合成了包含供体、电子传导和锚定基团的新型有机敏化剂。功能化的不对称有机敏化剂 3-5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) 和 3 -5'-[N,N-双(9,9-二甲基芴-2-基)苯基]-2,2'-双噻吩-5-基}-2-氰基-丙烯酸(JK-2)，在锚定在 TiO2 薄膜上，表现出前所未有的入射光子电流转换效率为 91%。使用含有 0.6 M-甲基-N-丁基咪唑鎓碘化物、0.04 M 碘、0.025 M LiI、0.05 M 硫氰酸胍和 0.28 M 叔丁基吡啶的 15/85 (v/v) 电解液的光伏数据戊腈和乙腈的混合物显示短路光电流密度为 14.0 +/- 0.2 mA/cm2，753 +/- 10 mV 的开路电压和 0.76 +/-
• Dye-Sensitized Photoelectric Conversion Device
  申请人：Shigaki Koichiro

  公开号：US20090044857A1

  公开（公告）日：2009-02-19

  Disclosed is a photoelectric conversion device wherein a methine dye represented by the formula (1) below is supported by a thin film of oxide semiconductor particles arranged on a substrate. Also disclosed is a solar cell manufactured by using such a photoelectric conversion device. (In the formula (1), n represents an integer of 0-5; m represents an integer of 0-5; R 1 -R 4 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; X and Y independently represent a hydrogen atom; an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; Z represents an oxygen atom, a sulfur atom or the like; A 1 , A 2 , A 3 , A 4 and A 5 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; and rings a, b and c may be substituted.)

  本发明公开了一种光电转换装置，其中通过在基板上排列的氧化物半导体颗粒薄膜上支持以下式(1)所表示的甲烷染料。同时，本发明还公开了使用这种光电转换装置制造的太阳能电池。(在式(1)中，n表示0-5的整数；m表示0-5的整数；R1-R4独立地表示氢原子、可选取代芳香基残基、可选取代脂肪烃基残基或类似物；X和Y独立地表示氢原子、可选取代芳香基残基、可选取代脂肪烃基残基或类似物；Z表示氧原子、硫原子或类似物；A1、A2、A3、A4和A5独立地表示氢原子、可选取代芳香基残基、可选取代脂肪烃基残基或类似物；环a、b和c可以被取代。)
• DYE-SENSITIZED PHOTOELECTRIC CONVERSION DEVICE
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP1990373A1

  公开（公告）日：2008-11-12

  Disclosed is a photoelectric conversion device wherein a methine dye represented by the formula (1) below is supported by a thin film of oxide semiconductor particles arranged on a substrate. Also disclosed is a solar cell manufactured by using such a photoelectric conversion device. (In the formula (1), n represents an integer of 0-5; m represents an integer of 0-5; R1-R4 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; X and Y independently represent a hydrogen atom; an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; Z represents an oxygen atom, a sulfur atom or the like; A1, A2, A3, A4 and A5 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; and rings a, b and c may be substituted.)

  本发明公开了一种光电转换装置，在该装置中，由下式（1）表示的甲胺染料由布置在基板上的氧化物半导体颗粒薄膜支撑。还公开了一种利用这种光电转换装置制造的太阳能电池。 (在式 (1) 中，n 代表 0-5 的整数；m 代表 0-5 的整数；R1-R4 独立地代表氢原子、任选取代的芳香残基、任选取代的脂肪烃残基或类似物；X 和 Y 独立地代表氢原子、任选取代的芳香残基、任选取代的脂肪烃残基或类似物；Z代表氧原子、硫原子或类似原子；A1、A2、A3、A4 和 A5 独立地代表氢原子、任选取代的芳香残基、任选取代的脂肪烃残基或类似原子；环 a、b 和 c 可以被取代。)
• US8735720B2
  申请人：——

  公开号：US8735720B2

  公开（公告）日：2014-05-27
• Novel conjugated organic dyes containing bis-dimethylfluorenyl amino phenyl thiophene for efficient solar cell
  作者：Sanghoon Kim、Hyunbong Choi、Duckhyun Kim、Kihyung Song、Sang Ook Kang、Jaejung Ko

  DOI：10.1016/j.tet.2007.06.061

  日期：2007.9

  Two novel organic dyes (JK- 5 and JK- 6) containing bis-dimethylfluorenyl amino phenyl thiophene and additional methine unit are synthesized. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using these dyes. A solar-to-electric conversion efficiency of 5.12% and 4.78% is achieved with JK- 5 and JK- 6, respectively. (c) 2007 Elsevier Ltd. All rights reserved.