4,4′-bis(2-carboxyvinyl)-2,2'-bipyridine | 773130-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4′-bis(2-carboxyvinyl)-2,2'-bipyridine
• 英文别名: 2,2'-bipyridine-4,4'-diacrylic acid；4,4'-bis(carboxyvinyl)-2,2'-bipyridine；3-[2-[4-(2-carboxyethenyl)pyridin-2-yl]pyridin-4-yl]prop-2-enoic acid
• CAS: 773130-04-4
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: BGCBZIDRQDDEPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 4,4′-bis(2-carboxyvinyl)-2,2'-bipyridine 以 N,N-二甲基甲酰胺 为溶剂， 生成 [Ru(II)(4,4'-bis(carboxyvinyl)-2,2'-bipyridine)2(NCS)2]
  参考文献：
  名称：

  Engineering of a Novel Ruthenium Sensitizer and Its Application in Dye-Sensitized Solar Cells for Conversion of Sunlight into Electricity

  摘要：

  A novel ligand 4,4'-bis(carboxyvinyl)-2,2'-bipyridine (L) and its ruthenium(II) complex [Ru(II)L-2(NCS)(2)] (K8) were synthesized and characterized by analytical, spectroscopic, and electrochemical techniques. The performance of the K8 complex as a charge transfer photosensitizer in nanocrystalline TiO2 based solar cells was studied. When the K8 complex anchored onto a nanocrystalline TiO2 film, we achieved very efficient sensitization yielding 77 +/- 5% incident photon-to-current efficiencies (IPCE) in the visible region using an electrolyte consisting of 0.6 M methyl-N-butyl imidiazolium iodide, 0.05 M iodine, 0.05 M Lil, and 0.5 M 4-tert-butylpyridine in a 50/50 (v/v) mixture of valeronitrile and acetonitrile. Under standard AM 1.5 sunlight, the complex K8 gave a short circuit photocurrent density of 18 +/- 0.5 mA/cm(2), and the open circuit voltage was 640 +/- 50 mV with fill factor of 0.75 +/- 0.05, corresponding to an overall conversion efficiency of 8.64 +/- 0.5%.

  DOI：

  10.1021/ic048810p
• 作为产物：
  描述：

  乙酸丁酯 、 2,2'-联吡啶-4,4'-二甲酸甲酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 platinum on activated charcoal 作用下， 以 四氢呋喃 为溶剂， 145.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 以98.5%的产率得到4,4′-bis(2-carboxyvinyl)-2,2'-bipyridine
  参考文献：
  名称：

  一种制备2,2’-联吡啶-4,4’-二丙烯酸的方法

  摘要：

  一种制备2,2'‑联吡啶‑4,4'‑二丙烯酸的方法，包括以下步骤：1）将2,2'‑联吡啶‑4,4'‑二甲酸甲酯、乙酸酯、催化剂加入到有机溶剂中混合，通入保护气，于120～150℃，压力2～5个标准大气压下反应25～48h；所述催化剂为铂碳催化剂和钯催化剂的混合；2）反应结束后，反应液经热过滤、浓缩后得到2,2'‑联吡啶‑4,4'‑二丙烯酸。本发明具有操作简单、合成条件温，收率高，收率大于98%；合成步骤简单，不需要无水处理，整体工艺成本较低；催化剂采用铂碳催化剂和钯催化剂的混合进行催化，用量少，催化剂成本消耗极低，同时该混合催化剂可重复使用，重复使用次数达到100次以上，重复使用率高。

  公开号：

  CN105906555B

文献信息

• Photosensitizer and photovoltaic device
  申请人：Yamanaka Noriyo

  公开号：US08471018B2

  公开（公告）日：2013-06-25

  Disclosed is a novel photosensitizer that can absorb light in a wide visible light region and in the case of a very thin film form, can enhance a light absorption efficiency by virtue of a large light absorption coefficient. The photosensitizer is used for metal oxide semiconductor electrodes and comprises a metal complex represented by a general formula ML1L2X2, wherein M is a group 8 transition metal of the periodic table, Xs are each independently a halogen atom, a cyano group, a thiocyanate group, an isothiocyanate group, an isocyanate group, an isocyanide group or a hydroxyl group, or a bidentate ligand in the case where Xs are bonded to one another, L1 and L2 are each a ligand having an aromatic ring, and either L1 or L2 has a functional group having a COOH group or PO(OH)2, and when the photosensitizer is adsorbed on a metal oxide semiconductor electrode via ligands L1 and L2, the difference ΔL between the energy levels of ligands L1 and L2 in their excited states, calculated in accordance with a GAUSSIAN03 quantum chemistry calculation program is 0.25 eV or more.

  揭示了一种新型光敏剂，可以在广泛的可见光区域吸收光线，并且在非常薄的薄膜形式下，由于具有较大的光吸收系数，可以增强光吸收效率。该光敏剂用于金属氧化物半导体电极，包括由通式ML1L2X2表示的金属配合物，其中M是周期表中的8族过渡金属，Xs分别是卤素原子、氰基、硫氰酸基、异硫氰酸基、异氰酸基、异氰化物基或羟基，或者在Xs彼此相互键合的情况下是双齿配体，L1和L2分别是具有芳香环的配体，其中L1或L2具有一个具有COOH基团或PO(OH)2基团的功能基团，当光敏剂通过配体L1和L2吸附在金属氧化物半导体电极上时，配体L1和L2在其激发态中的能级之间的能级差ΔL，根据GAUSSIAN03量子化学计算程序计算的结果为0.25电子伏或更高。
• Noble ruthenium-type sensitizer and method of preparing the same
  申请人：Dongjin Semichem Co., Ltd.

  公开号：US08288542B2

  公开（公告）日：2012-10-16

  The present invention relates to a ruthenium-type dye and a making method thereof, and more particularly, to a ruthenium-type dye which is used to manufacture a dye-sensitized solar cell, drastically improves a molar extinction coefficient to enhance efficiency of a solar cell with only a small amount of a dye and oxide semiconductor particles, allows a thin film solar cell element to be manufactured without difficulty and sharply reduces manufacturing costs of a solar cell, and a making method thereof.

  本发明涉及一种钌型染料及其制备方法，更具体地说，涉及一种钌型染料，用于制造染料敏化太阳能电池，显著提高摩尔消光系数，以仅使用少量染料和氧化物半导体粒子来提高太阳能电池的效率，使薄膜太阳能电池元件易于制造，并大幅降低太阳能电池的制造成本，以及其制备方法。
• 一种制备2,2’-联吡啶-4,4’-二丙烯酸的方法
  申请人：河南省商业科学研究所有限责任公司

  公开号：CN105906555B

  公开（公告）日：2018-04-24

  一种制备2,2'‑联吡啶‑4,4'‑二丙烯酸的方法，包括以下步骤：1）将2,2'‑联吡啶‑4,4'‑二甲酸甲酯、乙酸酯、催化剂加入到有机溶剂中混合，通入保护气，于120～150℃，压力2～5个标准大气压下反应25～48h；所述催化剂为铂碳催化剂和钯催化剂的混合；2）反应结束后，反应液经热过滤、浓缩后得到2,2'‑联吡啶‑4,4'‑二丙烯酸。本发明具有操作简单、合成条件温，收率高，收率大于98%；合成步骤简单，不需要无水处理，整体工艺成本较低；催化剂采用铂碳催化剂和钯催化剂的混合进行催化，用量少，催化剂成本消耗极低，同时该混合催化剂可重复使用，重复使用次数达到100次以上，重复使用率高。
• Engineering of a Novel Ruthenium Sensitizer and Its Application in Dye-Sensitized Solar Cells for Conversion of Sunlight into Electricity
  作者：C. Klein、Md. K. Nazeeruddin、P. Liska、Davide Di Censo、N. Hirata、E. Palomares、J. R. Durrant、M. Grätzel

  DOI：10.1021/ic048810p

  日期：2005.1.1

  A novel ligand 4,4'-bis(carboxyvinyl)-2,2'-bipyridine (L) and its ruthenium(II) complex [Ru(II)L-2(NCS)(2)] (K8) were synthesized and characterized by analytical, spectroscopic, and electrochemical techniques. The performance of the K8 complex as a charge transfer photosensitizer in nanocrystalline TiO2 based solar cells was studied. When the K8 complex anchored onto a nanocrystalline TiO2 film, we achieved very efficient sensitization yielding 77 +/- 5% incident photon-to-current efficiencies (IPCE) in the visible region using an electrolyte consisting of 0.6 M methyl-N-butyl imidiazolium iodide, 0.05 M iodine, 0.05 M Lil, and 0.5 M 4-tert-butylpyridine in a 50/50 (v/v) mixture of valeronitrile and acetonitrile. Under standard AM 1.5 sunlight, the complex K8 gave a short circuit photocurrent density of 18 +/- 0.5 mA/cm(2), and the open circuit voltage was 640 +/- 50 mV with fill factor of 0.75 +/- 0.05, corresponding to an overall conversion efficiency of 8.64 +/- 0.5%.