5,5-dimethyl-2-(3-hexyl-2-thienyl)-1,3,2-dioxaborinane | 817181-84-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 5,5-dimethyl-2-(3-hexyl-2-thienyl)-1,3,2-dioxaborinane
• 英文别名: 2-(3-hexylthiophen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane；5,5-dimethyl-2-(3-hexylthiophen-2-yl)-1,3,2-dioxaborinane
• CAS: 817181-84-3
• 化学式: C₁₅H₂₅BO₂S
• 分子量: 280.239
• InChiKey: XGMZNFOPPSSSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-(3-hexyl-2-thienyl)-1,3,2-dioxaborinane 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 17.5h， 生成 2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties

  摘要：

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.032

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。
• 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。
• 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.
• Near-Infrared Absorbing Boron-dibenzopyrromethenes that Serve As Light-Harvesting Sensitizers for Polymeric Solar Cells
  作者：Yuji Kubo、Kazuki Watanabe、Ryuhei Nishiyabu、Rieko Hata、Akinori Murakami、Takayuki Shoda、Hitoshi Ota

  DOI：10.1021/ol201770g

  日期：2011.9.2

  Hexylthiophene-conjugated boron-dibenzopyrromethenes with benzo[1,3,2]oxazaborinine rings, 1, that absorb near-infrared light with relatively high molecular extinction coefficients have been synthesized. The incorporation of 3-hexylthiophene-conjugated dye 1a at a blend ratio of 5 wt % into a polymeric solar cell based on a P3HT/indene-C-70 bisadduct (IC(70)BA) bulk heterojunction structure Improved power conversion efficiency from 3.7 to 4.3%. The present work suggests that well-defined near-infrared absorbing BODIPY analogues can potentially be used as photosensitizers in polymeric solar cells.
• Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties
  作者：Ken-ichi Saitou、Ryuhei Nishiyabu、Masahiko Iyoda、Yuji Kubo

  DOI：10.1016/j.tet.2011.10.032

  日期：2011.12

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.