9-ethyl-3-(4,3',3''-trihexyl[2,2';5',2'']terthiophen-5-yl)-9H-carbazole | 917561-55-8

• 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: 9-ethyl-3-(4,3',3''-trihexyl[2,2';5',2'']terthiophen-5-yl)-9H-carbazole
• 英文别名: 9-Ethyl-3-[3-hexyl-5-[3-hexyl-5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]carbazole
• CAS: 917561-55-8
• 化学式: C₄₄H₅₅NS₃
• 分子量: 694.125
• InChiKey: RAIHPIINLLKEHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-ethyl-3-(4,3',3''-trihexyl[2,2';5',2'']terthiophen-5-yl)-9H-carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到3-(5''-bromo-4,3',3''-trihexyl[2,2';5',2'']terthiophen-5-yl)-9-ethyl-9H-carbazole
  参考文献：
  名称：

  Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics

  摘要：

  We designed and synthesized new alkyl-functionalized organic dyes, MK-1 and MK-2, for dye-sensitized solar cells (DSSCs). Based on the MK-2 dye, a high performance of efficiency (eta, 7.7%; short-circuit current density Jsc = 14.0 mA cm-2, open-circuit voltage Voc = 0.74 V, and fill factor FF = 0.74) was achieved under AM 1.5 G irradiation (100 mW cm-2). Remarkably, the relatively higher Voc for DSSCs based on MK-1 and MK-2 dyes, which have long alkyl chains, were observed among the organic dyes caused by the increasing of the electron lifetime in the conduction band of TiO2. Our molecular design of alkyl-functionalized dyes strongly suggests the promising performance of molecular photovoltaics based on organic dyes.

  DOI：

  10.1021/ja0645640
• 作为产物：
  描述：

  3-(5'-bromo-4,3'-dihexyl[2,2']bithiophenyl-5-yl)-9-ethyl-9H-carbazole 、 5,5-dimethyl-2-(3-hexyl-2-thienyl)-1,3,2-dioxaborinane 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以85%的产率得到9-ethyl-3-(4,3',3''-trihexyl[2,2';5',2'']terthiophen-5-yl)-9H-carbazole
  参考文献：
  名称：

  Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics

  摘要：

  We designed and synthesized new alkyl-functionalized organic dyes, MK-1 and MK-2, for dye-sensitized solar cells (DSSCs). Based on the MK-2 dye, a high performance of efficiency (eta, 7.7%; short-circuit current density Jsc = 14.0 mA cm-2, open-circuit voltage Voc = 0.74 V, and fill factor FF = 0.74) was achieved under AM 1.5 G irradiation (100 mW cm-2). Remarkably, the relatively higher Voc for DSSCs based on MK-1 and MK-2 dyes, which have long alkyl chains, were observed among the organic dyes caused by the increasing of the electron lifetime in the conduction band of TiO2. Our molecular design of alkyl-functionalized dyes strongly suggests the promising performance of molecular photovoltaics based on organic dyes.

  DOI：

  10.1021/ja0645640

文献信息

• ORGANIC COMPOUND, SEMICONDUCTOR FILM ELECTRODE EMPLOYING THE ORGANIC COMPOUND, PHOTOELECTRIC CONVERSION ELEMENT EMPLOYING THE ORGANIC COMPOUND, AND PHOTOELECTROCHEMICAL SOLAR CELL EMPLOYING THE ORGANIC COMPOUND
  申请人：Koumura Nagatoshi

  公开号：US20100174095A1

  公开（公告）日：2010-07-08

  The present invention provides: an organic compound increasing an open circuit voltage, and showing high photoelectric conversion efficiency; a semiconductor film electrode employing the organic compound as a dye; a photoelectric conversion element employing the semiconductor film electrode; and a photoelectrochemical solar cell employing the photoelectric conversion element. The organic compound is represented by the following general formula: wherein A is a carbazole ring; L 1 is an electron transfer linking group having at least one heterocyclic ring selected from the group consisting of a thiophene ring, a furan ring, a pyrrole ring, and a condensed heterocyclic ring formed from any combinations of these rings; R is a substituent group bound to at least one electron transfer linking group selected from the group consisting of an alkyl group, an alkoxy group, and an aryl group; X is at least one electron withdrawing group selected from the group consisting of a cyano group, a carboxylic acid group, an ester group, an amide group, a trifluoromethyl group, a pentafluoroethyl group, a sulfonate group, and a trifluoromethanesulfonate group; M is a hydrogen atom or a salt-forming cation; and n is an integer of 1 to 12.

  本发明提供了一种有机化合物，可以增加开路电压并显示高光电转换效率；一种将该有机化合物作为染料的半导体薄膜电极；一种采用该半导体薄膜电极的光电转换元件；以及一种采用光电转换元件的光电化学太阳能电池。该有机化合物由下列通用式表示：其中A为咔唑环；L1为至少含有一种来自噻吩环、呋喃环、吡咯环和由这些环的任意组合形成的缩合杂环的杂环环的电子转移连接基团；R为与至少一种来自烷基、烷氧基和芳基的电子转移连接基团结合的取代基团；X为至少一种来自氰基、羧基、酯基、酰胺基、三氟甲基基团、五氟乙基基团、磺酸基团和三氟甲磺酸基团的电子提取基团；M为氢原子或形成盐的阳离子；n为1至12的整数。
• US7973172B2
  申请人：——

  公开号：US7973172B2

  公开（公告）日：2011-07-05
• Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics
  作者：Nagatoshi Koumura、Zhong-Sheng Wang、Shogo Mori、Masanori Miyashita、Eiji Suzuki、Kohjiro Hara

  DOI：10.1021/ja0645640

  日期：2006.11.1

  We designed and synthesized new alkyl-functionalized organic dyes, MK-1 and MK-2, for dye-sensitized solar cells (DSSCs). Based on the MK-2 dye, a high performance of efficiency (eta, 7.7%; short-circuit current density Jsc = 14.0 mA cm-2, open-circuit voltage Voc = 0.74 V, and fill factor FF = 0.74) was achieved under AM 1.5 G irradiation (100 mW cm-2). Remarkably, the relatively higher Voc for DSSCs based on MK-1 and MK-2 dyes, which have long alkyl chains, were observed among the organic dyes caused by the increasing of the electron lifetime in the conduction band of TiO2. Our molecular design of alkyl-functionalized dyes strongly suggests the promising performance of molecular photovoltaics based on organic dyes.