3,8-dioctyl-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione | 1201694-57-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3,8-dioctyl-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione
• 英文别名: 7,16-Dioctyl-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene-9,18-dione；7,16-dioctyl-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene-9,18-dione
• CAS: 1201694-57-6
• 化学式: C₃₂H₃₈O₂S₂
• 分子量: 518.785
• InChiKey: HWBUZYGHWNFLPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,8-dioctyl-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione 在 N-溴代丁二酰亚胺(NBS) 、 hydrazine hydrate 、 potassium tert-butylate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 氯仿 、 二甲基亚砜 为溶剂， 反应 16.5h， 生成 2,7-dibromo-3,8-dioctyl-4,4,9,9-tetrakis(4-phenylbutyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  10.1002/bkcs.12891

  摘要：

  AbstractThree novel non‐fullerene acceptors (NFAs) (PhBu‐IDT‐BT‐IC, PhBu‐IDT‐BT‐IC4F and PhBu‐IDT‐BT‐IC4Cl) based on 3,8‐dioctyl‐indaceno[1,2‐b:5,6‐b’]dithiophene (IDT) core have been designed and synthesized with and without halogen (F and Cl) substitution. The NFAs showed high thermal stability. The ultraviolet–visible absorption studies in solution and thin film for the three acceptors revealed maximum absorption from 687 to 732 nm and 731 to 847 nm, respectively. The onset of absorption in the thin film was found to be extending up to around 960 nm for PhBu‐IDT‐BT‐IC4Cl. The optical band gap ranged from 1.30 to 1.41 eV, which are very low and useful for photovoltaic application. The introduction of halogen appreciably altered the LUMO energy levels, whereas the HOMO energy levels were nearly intact. These small molecule non‐fullerene acceptors could be used as potential acceptors in bulk heterojunction organic photovoltaic (BHJ‐OPV) applications.

  DOI：

  10.1002/bkcs.12891
• 作为产物：
  描述：

  2,5-Bis(4-octylthiophen-2-yl)benzene-1,4-dicarbonyl chloride 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以30%的产率得到3,8-dioctyl-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione
  参考文献：
  名称：

  Synthesis and properties of thiophene-functionalized π-extended tetrathiafulvalenes

  摘要：

  Two molecular ensembles composed of an array of thiophene-extended tetrathiafulvalene-thiophene were synthesized using Stille coupling and Horner-Wittig reaction as the key steps. Electrochemical redox and electronic absorption properties were investigated by voltammetric and UV-vis spectroscopic analyses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.150

文献信息

• ORGANIC COLOURANT AND USES THEREOF IN PHOTOVOLTAIC CELLS
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：US20140290748A1

  公开（公告）日：2014-10-02

  The present invention relates to an organic colorant corresponding to one of the following structures (I) or (II): eD-pi-conjugated chromophore-L-A  (I) A-L-pi-conjugated chromophore-eD  (II) in which eD represents an electron donor segment; L represents a covalent bond or a spacer segment; A represents an electron attractor segment able to form a covalent bond with a semi-conductor; the pi-conjugated chromophore comprising at least two aromatic rings, at least one of which is a thiophene, selenophene or furan type ring. The present invention relates to the use thereof as photosensitizer in a photovoltaic device and said photovoltaic device.

  本发明涉及与以下结构（I）或（II）之一相对应的有机染料： eD-π-共轭色团-L-A  （I） A-L-π-共轭色团-eD  （II） 其中，eD代表电子给体片段；L代表共价键或间隔片段；A代表能够与半导体形成共价键的电子吸引片段；π-共轭色团包括至少两个芳香环，其中至少一个是噻吩、硒吩或呋喃型环。本发明涉及将其用作光伏器件中的光敏剂以及该光伏器件。
• COLORANT ORGANIQUE ET SES UTILISATIONS DANS LES CELLULES PHOTOVOLTAÏQUES
  申请人：Commissariat à l'Énergie Atomique et aux Énergies Alternatives

  公开号：EP2776515A1

  公开（公告）日：2014-09-17
• ELECTRODE COATED WITH REDOX POLYMERS CONTAINING DIONE UNITS, PREPARATION METHOD AND USES THEREOF
  申请人：Commissariat à l'Energie Atomique et aux Energies Alternatives

  公开号：EP3282461B1

  公开（公告）日：2020-05-06
• US9171676B2
  申请人：——

  公开号：US9171676B2

  公开（公告）日：2015-10-27
• [EN] ORGANIC COLOURANT AND USES THEREOF IN PHOTOVOLTAIC CELLS<br/>[FR] COLORANT ORGANIQUE ET SES UTILISATIONS DANS LES CELLULES PHOTOVOLTAÏQUES
  申请人：COMMISSARIAT ENERGIE ATOMIQUE

  公开号：WO2013068588A1

  公开（公告）日：2013-05-16

  La présente invention concerne un colorant organique répondant à l'une des structures (I) ou (II) suivantes: eD –chromophore pi-conjugué –L –A (I) A –L –chromophore pi-conjugué –eD (II) dans lesquelles eD représente un segment électro-donneur; L représente une liaison covalente ou un segment espaceur; A représente un segment électro-attracteur apte à former une liaison covalente avec un semi-conducteur; le chromophore pi- conjugué comprenant au moins deux cycles aromatiques dont au moins un est un cycle de type thiophène, sélénophène ou furanne. La présente invention concerne son utilisation comme photosensibilisateur dans un dispositif photovoltaïque et ledit dispositif photovoltaïque.