双(2-碘-3-噻吩基)甲酮 | 474416-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 双(2-碘-3-噻吩基)甲酮
• 中文别名: 双(2-碘噻吩-3-基)甲酮
• 英文名称: bis(2-iodo-3-thienyl)methanone
• 英文别名: bis(2-iodo-3-thienyl) ketone；Bis(2-iodothiophen-3-yl)methanone
• CAS: 474416-61-0
• 化学式: C₉H₄I₂OS₂
• 分子量: 446.071
• InChiKey: XLSNWYDMCRRAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  双(2-碘-3-噻吩基)甲酮 在 sodium perborate tetrahydrate 、 铜 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 2-[3-(13-Hydroxy-2,6,10,16,20,24-hexamethylpentacosan-13-yl)thiophen-2-yl]thiophen-3-ol
  参考文献：
  名称：

  高分子化合物

  摘要：

  本发明涉及高分子化合物。含有下述高分子化合物的光电转换元件的光电转换效率高，所述高分子化合物具有由式(1)表示的结构单元。式中，X1和X2相同或不同，表示氮原子或＝CH-；Y1表示硫原子、氧原子、硒原子、-N(R1)-或-CR2＝CR3-；R1、R2和R3相同或不同，表示氢原子或取代基；W1表示氰基、具有氟原子的1价有机基团或卤素原子；W2表示氰基、具有氟原子的1价有机基团、卤素原子或氢原子。

  公开号：

  CN105439976A
• 作为产物：
  描述：

  di(3-thienyl)methanol 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 生成 双(2-碘-3-噻吩基)甲酮
  参考文献：
  名称：

  A Versatile Synthesis of Long-Wavelength-Excitable BODIPY Dyes from Readily Modifiable Cyclopenta[2,1-b:3,4-b′]dithiophenes

  摘要：

  Knoevenagel condensation of a simple methylated borondipyrromethene (Bodipy) with 4,4'-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm.

  DOI：

  10.1055/s-0033-1341278

文献信息

• 用于形成高分子化合物的化合物
  申请人：住友化学株式会社

  公开号：CN105601662A

  公开（公告）日：2016-05-25

  本发明提供一种在光电转换元件中所含的有机层中使用时，短路电流密度和光电转换效率更大的化合物。具体而言，本发明提供具有式一种式(5)所表示的化合物，式中，R52和R53相同或不同，表示氢原子、卤原子、烷基、烷基氧基、烷基硫基、芳基、芳基氧基、芳基硫基、芳基烷基、芳基烷基氧基、芳基烷基硫基、酰基、酰氧基、酰胺基、酰亚胺基、氨基、取代氨基、取代甲硅烷基、取代甲硅烷基氧基、取代甲硅烷基硫基、取代甲硅烷基氨基、1价的杂环基、杂环氧基、杂环硫基、芳基烯基、芳基炔基、羧基或氰基，W1和W2相同或不同，表示氢原子、卤原子、烷基磺酸酯基、芳基磺酸酯基、芳基烷基磺酸酯基、硼酸酯残基、锍甲基、鳞甲基、膦酸酯甲基、单卤代甲基、硼酸残基、甲酰基、乙烯基或有机锡残基。
• A New, Improved and Convenient Synthesis of 4H-Cyclopenta[2,1-b:3,4-b′]-dithiophen-4-one
  作者：Jacek Z. Brzeziński、John R. Reynolds

  DOI：10.1055/s-2002-31958

  日期：——

  A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CDT) (1) is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol (13), its subsequent oxidation to the bis(2-iodo-3-thienyl) ketone (14) which after Ullmann coupling yielded the title compound 1.

  本文描述了一种新的、高效的4H-环戊并[2,1-b:3,4-b′]二噻吩-4-酮（CDT）（1）的三步合成方法。具体方法是：通过一步法、位点特异性合成双（2-碘-3-噻吩基）甲醇（13），将其氧化为双（2-碘-3-噻吩基）酮（14），后者经过乌尔曼偶联反应后得到标题化合物1。
• EVAPORABLE ORGANIC SEMICONDUCTIVE MATERIAL AND USE THEREOF IN AN OPTOELECTRONIC COMPONENT
  申请人：Hildebrandt Dirk

  公开号：US20130167930A1

  公开（公告）日：2013-07-04

  The invention relates to compounds of general formula IIIa and their use in optoelectronic components.

  本发明涉及通式IIIa化合物及其在光电组件中的使用。
• Macromolecular compound
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US10290809B2

  公开（公告）日：2019-05-14

  The present invention provides a macromolecular compound by which the short-circuit current density and the photoelectric conversion efficiency are enhanced when the macromolecular compound is used in an organic layer contained in a photovoltaic cell. Specifically, the present invention provides a macromolecular compound having a structural unit represented by Formula (1): wherein Ar1 and Ar2 are the same as or different from each other and represent a trivalent heterocyclic group; X1 represents —O—, —S—, —C(═O)—, —S(═O)—, —SO2—, —Si(R3)(R4)—, —N(R5)—, —B(R6)—, —P(R7)—, or —P(═O)(R8)—; and R51 represents an alkyl group having 6 or more carbon atoms, an alkyloxy group having 6 or more carbon atoms, an alkylthio group having 6 or more carbon atoms, an aryl group having 6 or more carbon atoms, an aryloxy group having 6 or more carbon atoms, an arylthio group having 6 or more carbon atoms, an arylalkyl group having 7 or more carbon atoms, an arylalkyloxy group having 7 or more carbon atoms, an arylalkylthio group having 7 or more carbon atoms, an acyl group having 6 or more carbon atoms, or an acyloxy group having 6 or more carbon atoms.

  本发明提供了一种高分子化合物，当该高分子化合物用于光伏电池中的有机层时，可提高短路电流密度和光电转换效率。具体而言，本发明提供了一种高分子化合物，其结构单元由式（1）表示： 其中 Ar1 和 Ar2 彼此相同或不同，代表三价杂环基团；X1 代表-O-、-S-、-C(═O)-、-S(═O)-、-SO2-、-Si(R3)(R4)-、-N(R5)-、-B(R6)-、-P(R7)- 或-P(═O)(R8)-；和 R51 代表具有 6 个或更多碳原子的烷基、具有 6 个或更多碳原子的烷氧基、具有 6 个或更多碳原子的烷硫基、具有 6 个或更多碳原子的芳基、具有 6 个或更多碳原子的芳氧基、具有 6 个或更多碳原子的芳硫基、具有 7 个或更多碳原子的芳烷基、具有 7 个或更多碳原子的芳烷氧基、具有 7 个或更多碳原子的芳烷基硫基、具有 6 个或更多碳原子的酰基或具有 6 个或更多碳原子的酰氧基。
• Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends
  作者：Chiu-Hsiang Chen、Chao-Hsiang Hsieh、Martin Dubosc、Yen-Ju Cheng、Chain-Shu Hsu

  DOI：10.1021/ma902206u

  日期：2010.1.26

  Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)(m)-(thiophene acceptor)(n), were rationally designed and successfully synthesized by the palladium-catalyzed Stille Coupling, The 4H-cyclopenta[2, 1-b:3,4-b']dithiophene (CPDT) unit serves as the donor for P1-P4, while file benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3.2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BR > QU presumably due to the quinoid form Population in the polymers, the optical band gaps call be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that file two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects oil the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based oil ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows it higher band gap with strong absorption in visible region, while PCPDTBT-has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P-1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC7, BM (PCE = 1.4%) or P1/PC71 BM (PCE = 2.0%,,) Linder the identical conditions. Such an improvement is ascribed to file complementary absorption and compatible structure of P1 and PCPDTBT polymers.