3-ethyl-5-(3-carboxymethyl-4-oxo-thiazolidin-2-ylidene)rhodanine | 872416-43-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-ethyl-5-(3-carboxymethyl-4-oxo-thiazolidin-2-ylidene)rhodanine
• 英文别名: 3-Thiazolidineacetic acid, 2-(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)-4-oxo-；2-[2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid
• CAS: 872416-43-8
• 化学式: C₁₀H₁₀N₂O₄S₃
• 分子量: 318.398
• InChiKey: ZWDXGFNMAMHQIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-ethyl-5-(3-carboxymethyl-4-oxo-thiazolidin-2-ylidene)rhodanine 、 11-Hexyl-5,6-dihydrobenzo[b][1]benzazepine-3-carbaldehyde 在 溶剂黄146 、 ammonium acetate 作用下， 反应 2.5h， 生成 2-(3'-ethyl-5-((5-hexyl-10,11-dihydro-5H-dibenzo[b,f]azepin-2-yl)methylene)-4,4'-dioxo-2'-thioxo-3',4,4',5-tetrahydro-2'H,3H-[2,5'-bithiazolylidene]-3-yl)acetic acid
  参考文献：
  名称：

  DYE, PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME, PHOTOELECTROCHEMICAL CELL, AND METHOD OF PRODUCING DYE

  摘要：

  一种染料，其结构由式（1A）表示：其中A代表与碳-氮键一起形成环的原子团；Y1A和Y2A中至少一个代表酸性基团，当它们各自代表酸性基团时，它们可以相同也可以不同，或者当它们中只有一个代表酸性基团时，另一个代表电子吸引基团；D代表给染料的基团；n代表大于等于1的整数；L代表单键或二价连接基团；Y3A代表酸性基团。

  公开号：

  US20110213144A1
• 作为产物：
  描述：

  3-Thiazolidineacetic acid, 2-(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)-4-oxo-, ethyl ester 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 4.0h， 生成 3-ethyl-5-(3-carboxymethyl-4-oxo-thiazolidin-2-ylidene)rhodanine
  参考文献：
  名称：

  DYE, PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME, PHOTOELECTROCHEMICAL CELL, AND METHOD OF PRODUCING DYE

  摘要：

  一种染料，其结构由式（1A）表示：其中A代表与碳-氮键一起形成环的原子团；Y1A和Y2A中至少一个代表酸性基团，当它们各自代表酸性基团时，它们可以相同也可以不同，或者当它们中只有一个代表酸性基团时，另一个代表电子吸引基团；D代表给染料的基团；n代表大于等于1的整数；L代表单键或二价连接基团；Y3A代表酸性基团。

  公开号：

  US20110213144A1

文献信息

• Indoline Dyes with Benzothiazole Unit for Dye-sensitized Solar Cells
  作者：Tamotsu Horiuchi、Tohru Yashiro、Ryo Kawamura、Satoshi Uchida、Hiroshi Segawa

  DOI：10.1246/cl.160084

  日期：2016.5.5

  We report a new series of indoline dyes with a donor–aromatic–acceptor (D–π–A) structure. D–π–A metal-free organic dyes with indoline–benzothiazole–rhodanine units were synthesized and their photovoltaic performances were evaluated. The photoelectric conversion efficiency (η) of the indoline–benzothiazole–rhodanine dye is 3.7%, while that of the indoline–thiophene–rhodanine dye is 0.9% under the same conditions. The incident photon-to-current conversion efficiencies (IPCEs) of these dyes are 60% and 25%, respectively, at 500 nm. To understand their electronic structures, the geometries of the dyes were optimized by density functional theory (DFT) calculations at the 6-31G(d) level using a B3LYP exchange-correlation functional. As a result, the localized highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the indoline–benzothiazole–rhodanine dye were obtained and were compared with those of the indoline–thiophene–rhodanine dye.

  我们报告了一系列具有供体-芳香族-受体（D-π-A）结构的新二氢吲哚染料。合成了具有二氢吲哚-苯并噻唑-绕丹宁单元的D-π-A无金属有机染料，并评估了它们的光伏性能。在相同条件下，二氢吲哚-苯并噻唑-绕丹宁染料的光电转换效率（η）为3.7%，而二氢吲哚-噻吩-绕丹宁染料的光电转换效率为0.9%。这些染料在 500 nm 处的入射光子到电流的转换效率 (IPCE) 分别为 60% 和 25%。为了了解它们的电子结构，使用 B3LYP 交换相关泛函在 6-31G(d) 水平上通过密度泛函理论 (DFT) 计算优化了染料的几何形状。结果，获得了二氢吲哚-苯并噻唑-绕丹宁染料的局域最高占据分子轨道（HOMO）和最低未占分子轨道（LUMO），并与二氢吲哚-噻吩-绕丹宁染料进行了比较。
• Novel thiophene-conjugated indolinedyes for zinc oxide solar cells
  作者：Takuya Dentani、Yasuhiro Kubota、Kazumasa Funabiki、Jiye Jin、Tsukasa Yoshida、Hideki Minoura、Hidetoshi Miura、Masaki Matsui

  DOI：10.1039/b808959k

  日期：——

  The application of a series of thiophene-conjugated indoline dyes for zinc oxide solar cells, prepared by the one-step cathode deposition template method, was examined. The introduction of thiophene ring(s) into D131-type indoline dye improved the cell performance due to their appropriate energy levels and bathochromic shift in the UV-vis absorption band on zinc oxide. It is important for the oxidation potential (Eox) of dyes to have a more positive value than ca. 0.25 V vs. Fc/Fc+ in acetonitrile in order to show a high (>70%) incident photon-to-current efficiency.

  研究人员采用一步阴极沉积模板法制备了一系列用于氧化锌太阳能电池的噻吩共轭吲哚啉染料。在 D131 型吲哚啉染料中引入噻吩环后，由于其在氧化锌上具有适当的能级和紫外可见吸收带的浴色偏移，电池性能得到了改善。染料的氧化电位（Eox）必须大于 0.25 V（在乙腈中与 Fc/Fc+ 的比值），这样才能显示出较高的（大于 70%）入射光子到电流的效率。
• Comparison of performance between benzoindoline and indoline dyes in zinc oxide dye-sensitized solar cell
  作者：Masaki Matsui、Masaya Kotani、Yasuhiro Kubota、Kazumasa Funabiki、Jiye Jin、Tsukasa Yoshida、Shinji Higashijima、Hidetoshi Miura

  DOI：10.1016/j.dyepig.2011.02.009

  日期：2011.11

  The cell performance of novel benzoindoline dyes on zinc oxide prepared by template cathode electro-deposition method was compared with that of known indoline dyes. Among cyanoacrylic, single and double rhodanine acetic acid derivatives, the cyanoacrylic benzoindoline dye showed better performance than the indoline dye (D131) due to larger J(sc) value which comes from its positive E., level and bathochromic UV-vis absorption band. (C) 2011 Elsevier Ltd. All rights reserved.
• Substituent effects in a double rhodanine indoline dye on performance of zinc oxide dye-sensitized solar cell
  作者：Masaki Matsui、Tomoki Fujita、Yasuhiro Kubota、Kazumasa Funabiki、Jiye Jin、Tsukasa Yoshida、Hidetoshi Miura

  DOI：10.1016/j.dyepig.2009.12.009

  日期：2010.7

  The solar-light-to-electricity conversion efficiency of substituted indoline dyes depended on short-circuit photocurrent density which is affected by maximum incident photon-to-current efficiency. The oxidation potential of the double rhodanine indoline dyes needed to be >similar to 0.2 V vs Fc/Fc(+) in acetonitrile to show high incident photon-to-current efficiency in a zinc oxide, dye-sensitized solar cell. To make a molecular design of highly efficient indoline dyes, the HOMO energy level should be more negative than similar to-4.9 eV by the DFT calculations. (C) 2010 Elsevier Ltd. All rights reserved.
• DYE, PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME, PHOTOELECTROCHEMICAL CELL, AND METHOD OF PRODUCING DYE
  申请人：Kobayashi Katsumi

  公开号：US20110213144A1

  公开（公告）日：2011-09-01

  A dye, having a structure represented by formula (1A): wherein A represents a group of atoms necessary for forming a ring together with the carbon-nitrogen bond; at least one of Y 1A and Y 2A represents an acidic group, in which when they each represent an acidic group, they may be the same as or different from each other, or when only one of them represents an acidic group, the other represents an electron-withdrawing group; D represents a group to give a dye; n represents an integer of 1 or greater; L represents a single bond or a divalent linking group; and Y 3A represents an acidic group.

  一种染料，其结构由式（1A）表示：其中A代表与碳-氮键一起形成环的原子团；Y1A和Y2A中至少一个代表酸性基团，当它们各自代表酸性基团时，它们可以相同也可以不同，或者当它们中只有一个代表酸性基团时，另一个代表电子吸引基团；D代表给染料的基团；n代表大于等于1的整数；L代表单键或二价连接基团；Y3A代表酸性基团。