3,3‴-dihexyl-5‴-iodo-[2,2':5',2":5",2‴-quaterthiophene]-5-carbaldehyde | 1346644-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,3‴-dihexyl-5‴-iodo-[2,2':5',2":5",2‴-quaterthiophene]-5-carbaldehyde
• 英文别名: 3,3'''-dihexyl-5'''-iodo-[2,2':5',2'':5'',2'''-quaterthiophene]-5-carbaldehyde；4-hexyl-5-[5-[5-(3-hexyl-5-iodothiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 1346644-08-3
• 化学式: C₂₉H₃₃IOS₄
• 分子量: 652.749
• InChiKey: MUZSGXYAMHETLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3‴-dihexyl-5‴-iodo-[2,2':5',2":5",2‴-quaterthiophene]-5-carbaldehyde 在 palladium 10% on activated carbon 吡啶 、 sodium phosphate dodecahydrate 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 26.0h， 生成 5-((5‴-(4-(diphenylamino)phenyl)-3,3‴-dihexyl-[2,2':5',2":5",2‴-quaterthiophene]-5-yl)methylene)-1-(2-ethylhexyl)-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  [EN] IMPROVED OLIGOTHIOPHENES
  [FR] OLIGOTHIOPHÈNES AMÉLIORÉS

  摘要：

  式（I）的化合物，其中T是从（a）组成的群体中独立选择的。变量R1、R2、R3、R4、R5、R6、R7、R8、R9、Ar、L和n的定义如本说明书中所述。这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。

  公开号：

  WO2011137487A1
• 作为产物：
  描述：

  3,3‴-dihexyl-[2,2':5',2":5",2‴-quaterthiophene]-5-carbaldehyde 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 以87.04%的产率得到3,3‴-dihexyl-5‴-iodo-[2,2':5',2":5",2‴-quaterthiophene]-5-carbaldehyde
  参考文献：
  名称：

  [EN] IMPROVED OLIGOTHIOPHENES
  [FR] OLIGOTHIOPHÈNES AMÉLIORÉS

  摘要：

  式（I）的化合物，其中T是从（a）组成的群体中独立选择的。变量R1、R2、R3、R4、R5、R6、R7、R8、R9、Ar、L和n的定义如本说明书中所述。这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。

  公开号：

  WO2011137487A1

文献信息

• OLIGOTHIOPHENES
  申请人：Evans Richard

  公开号：US20130042918A1

  公开（公告）日：2013-02-21

  Compounds of Formula (I): Wherein: R 1 and R 2 are independently selected from the group consisting of optionally substituted C 1 -C 20 alkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted aromatic, and optionally substituted heteroaromatic groups or R 1 and R 2 together with the nitrogen atom to which they are attached comprise an optionally substituted saturated or unsaturated ring which may optionally contain further heteroatoms selected from the group consisting of O, N and S, and may optionally be further fused to one or more other rings; Ar is selected from the group consisting of optionally substituted aromatic and optionally substituted heteroaromatic groups; L is a linker which is a direct bond or is selected from the group consisting of optionally substituted C 2 alkenylene and optionally substituted C 2 alkynylene; T is independently selected from the group consisting of: R 3 , R 4 and R 9 are independently selected from the group consisting of hydrogen, optionally substituted C 1 -C 10 alkyl, optionally substituted C 3 -C 8 cycloalkyl and optionally substituted C 1 -C 10 alkoxy groups, or a pair of groups selected from R 3 , R 4 and R 9 may together with the carbon atoms to which they are attached comprise an optionally substituted saturated or unsaturated ring which may optionally contain one or more heteroatoms selected from the group consisting of O, N and S, and may optionally be further fused to one or more other rings; R 5 is selected from the group consisting of hydrogen, optionally substituted C 1 -C 8 alkyl, optionally substituted C 3 -C 8 cycloalkyl, and optionally substituted aromatic groups; R 6 is selected from the group consisting of optionally substituted C 1 -C 8 alkyl, optionally substituted C 1 -C 8 perfluorinated alkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted aromatic, and optionally substituted heteroaromatic groups; R 7 is selected from the group consisting of optionally substituted C 1 -C 30 alkyl wherein one or more carbon atoms of the alkyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 3 -C 8 cycloalkyl; optionally substituted C 2 -C 12 alkenyl wherein one or more carbon atoms of the alkenyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 2 -C 8 alkynyl wherein one or more carbon atoms of the alkynyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 3 -C 12 alkoxy; optionally substituted aromatic; and optionally substituted heteroaromatic groups; wherein R 8 is hydrogen or R 6 , and n is an integer of 1 to 10. The compounds are capable of charge transportation and have application in organic photovoltaic devices such as dye sensitised solar cells.

  分子式(I)的化合物： 其中： R1和R2独立地选自选自取代的C1-C20烷基，取代的C3-C8环烷基，取代的芳香基和取代的杂芳基，或者R1和R2连同它们所附着的氮原子组成一个可选取代的饱和或不饱和环，该环可以选择进一步包含来自O、N和S的进一步杂原子，并且可以选择进一步融合到一个或多个其他环中； Ar选自选自取代的芳香基和取代的杂芳基； L是一个连接基，可以是直接键或选自可选取代的C2烯基和可选取代的C2炔基的群体； T独立地选自群体，包括： R3、R4和R9独立地选自氢，可选取代的C1-C10烷基，可选取代的C3-C8环烷基和可选取代的C1-C10甲氧基基团，或者选自R3、R4和R9中的一对基团，连同它们所附着的碳原子组成一个可选取代的饱和或不饱和环，该环可以选择进一步包含来自O、N和S的一个或多个杂原子，并且可以选择进一步融合到一个或多个其他环中； R5选自氢，可选取代的C1-C8烷基，可选取代的C3-C8环烷基和可选取代的芳香基团； R6选自可选取代的C1-C8烷基，可选取代的C1-C8全氟烷基，可选取代的C3-C8环烷基，可选取代的芳香基和可选取代的杂芳基； R7选自可选取代的C1-C30烷基，其中烷基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C3-C8环烷基；可选取代的C2-C12烯基，其中烯基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C2-C8炔基，其中炔基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C3-C12甲氧基；可选取代的芳香基；和可选取代的杂芳基；其中R8是氢或R6，n为1到10的整数。 这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。
• Molecular engineering for panchromatic absorbing oligothiophene donor–π–acceptor organic semiconductors
  作者：Akhil Gupta、Abdelselam Ali、Th. Birendra Singh、Ante Bilic、Udo Bach、Richard A. Evans

  DOI：10.1016/j.tet.2012.09.009

  日期：2012.11

  A series of three novel organic semiconductor molecules based on the donor it-bridge acceptor (D-pi-A) modular design have been designed, synthesised and characterised. These small organic molecules have a common donor (triphenylamine), pi-bridge (an alkylated tetrathiophene) and various acceptors to provide tuning of optical and electronic properties. The examined acceptors were dicyanovinylidene, cyanopyridone and oxoindenemalononitrile groups. These compounds were highly soluble in common organic solvents, such as chloroform, toluene and chlorobenzene. As acceptor strength increased from dicyanovinylidene to cyanopyridone to oxoindenemalononitrile groups, the wavelength of the longest wavelength absorption maximum increased (518, 587, 619 nm (solution)), the respective extinction coefficients increased (4.9x10(4), 6.3x10(4), 7.4x10(4) M-1 cm(-1)) and with increasing acceptor strength the band gap narrowed (1.63, 1.42 1.38 eV). Panchromatic absorbance was observed for the compounds comprising the cyanopyridone and oxoindenemalononitrile acceptors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• IMPROVED OLIGOTHIOPHENES
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：EP2566848A1

  公开（公告）日：2013-03-13