2,3-bis[3,4-bis[decyloxy]phenyl]-5,8-dibromoquinoxaline | 1138217-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-bis[3,4-bis[decyloxy]phenyl]-5,8-dibromoquinoxaline
• 英文别名: 5,8-Dibromo-2,3-bis(3,4-didecoxyphenyl)quinoxaline；5,8-dibromo-2,3-bis(3,4-didecoxyphenyl)quinoxaline
• CAS: 1138217-21-6
• 化学式: C₆₀H₉₂Br₂N₂O₄
• 分子量: 1065.21
• InChiKey: ROYUQPCJJFXHGT-UHFFFAOYSA-N

物化性质

• 沸点：
  896.6±65.0 °C(predicted)
• 密度：
  1.105±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  23.8
• 重原子数：
  68
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis[3,4-bis[decyloxy]phenyl]-5,8-dibromoquinoxaline 、 (噻吩并[3,2-B]噻吩-2-基)三丁基锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-di(thieno[3,2-b]thiophen-2-yl)-2,3-dihydroquinoxaline
  参考文献：
  名称：

  Thieno[3,2-b]thiophene as π-bridge at different acceptor systems for electrochromic applications

  摘要：

  Benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene are the units preferred in conducting polymers due to their electrochemical properties. There are no reports in the literature on polymers containing both moieties. In this study, novel benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene based monomers; 4-(3a,6a-dihydrothieno[3,2-b]thiophen-2-y1)-7-(thieno[3,2-b]thiophenyl) benzo[c][1,2,51selenadiazole (BSeTT) and 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromo-2,3dihydroquinoxaline (QTT) were synthesized via Stille Coupling and polymerized electrochemically. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV Vis NIR spectroscopy. Spectroelectrochemistry analysis of PBSeTT revealed an electronic transition at 525 nm corresponding to pi-pi* transition with a band gap of 0.93 eV whereas PQTT revealed electronic transitions at 440 and 600 nm corresponding to pi-pi*transitions with a band gap of 1.30 eV. Electrochromic investigations showed that PBSeTT has gray color PQTT switching between green and gray. Switching time of the polymers was evaluated by a kinetic study upon measuring the percent transmittance (%T) at the maximum contrast point. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.05.029
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 氢溴酸 、 溴 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 2,3-bis[3,4-bis[decyloxy]phenyl]-5,8-dibromoquinoxaline
  参考文献：
  名称：

  Thieno[3,2-b]thiophene as π-bridge at different acceptor systems for electrochromic applications

  摘要：

  Benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene are the units preferred in conducting polymers due to their electrochemical properties. There are no reports in the literature on polymers containing both moieties. In this study, novel benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene based monomers; 4-(3a,6a-dihydrothieno[3,2-b]thiophen-2-y1)-7-(thieno[3,2-b]thiophenyl) benzo[c][1,2,51selenadiazole (BSeTT) and 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromo-2,3dihydroquinoxaline (QTT) were synthesized via Stille Coupling and polymerized electrochemically. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV Vis NIR spectroscopy. Spectroelectrochemistry analysis of PBSeTT revealed an electronic transition at 525 nm corresponding to pi-pi* transition with a band gap of 0.93 eV whereas PQTT revealed electronic transitions at 440 and 600 nm corresponding to pi-pi*transitions with a band gap of 1.30 eV. Electrochromic investigations showed that PBSeTT has gray color PQTT switching between green and gray. Switching time of the polymers was evaluated by a kinetic study upon measuring the percent transmittance (%T) at the maximum contrast point. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.05.029

文献信息

• BENZOTRIAZOLE CONTAINING DONOR-ACCEPTOR TYPE POLYMER AS A MULTI-PURPOSE MATERIAL
  申请人：Toppare Levent Kamil

  公开号：US20100249367A1

  公开（公告）日：2010-09-30

  This invention is about a material which provides to observe all colors necessary for display technologies in a very small potential range. The material is a derivative of benzotriazole containing donor acceptor type conducting polymer which is soluble, fluorescent and can be used in LEDs, solar cells, electrochromic devices, smart windows and many other technologies.

  这项发明涉及一种材料，可以在非常小的电位范围内观察到显示技术所需的所有颜色。这种材料是苯并三唑衍生物，含有供体受体型导电聚合物，可溶性、荧光性，并可用于LED、太阳能电池、电致变色器件、智能窗户等许多其他技术中。
• US8324400B2
  申请人：——

  公开号：US8324400B2

  公开（公告）日：2012-12-04
• [EN] UNIQUE PROCESSABLE GREEN POLYMER WITH A TRANSMISSIVE OXIDIZED STATE FOR REALIZATION OF COMMERICAL RGB BASED ELECTROCHROMIC DEVICE APPLICATIONS<br/>[FR] POLYMÈRE VERT TRANSFORMABLE PARTICULIER PRÉSENTANT UN ÉTAT OXYDÉ TRANSMISSIF POUR LA RÉALISATION D'APPLICATIONS COMMERCIALES DE DISPOSITIFS ÉLECTROCHROMES À BASE RVB
  申请人：TOPPARE LEVENT KAMIL

  公开号：WO2009126118A1

  公开（公告）日：2009-10-15

  In the present invention a method for synthesis of neutral state green polymer PDOPEQ) is developed. The method developed in this invention is characterized by; a) obtaining 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromoquinoxaline, b) b) obtaining tributyl (2,3-dihydrothieno[3,4-b][l,4]dioxin-5-yl)stannane c) c) Using coupling to attach donor EDOT moieties to the acceptor quinoxaline unit to give the title compound (DOPEQ) in satisfactory yields; d) obtaining neutral state green polymer (PDOPEQ) by using either electrochemical or chemical methods. The polymers synthesized up to date mainly absorb/reflect blue and red colors in the reduced state. Conversely, to obtain a green colored polymer in the reduced state, one should have two absorption bands centered at the blue and red regions of the visible spectrum and moreover, these absorption bands should be manipulated in the same manner at applied potentials.
• [EN] BENZOTRIAZOLE CONTAINING DONOR-ACCEPTOR TYPE POLYMER AS A MULTI-PURPOSE MATERIAL<br/>[FR] POLYMÈRE DE TYPE DONNEUR-ACCEPTEUR CONTENANT DU BENZOTRIAZOLE EN TANT QUE MATIÈRE POLYVALENTE
  申请人：TOPPARE LEVENT KAMIL

  公开号：WO2010114497A1

  公开（公告）日：2010-10-07

  This invention is about a material which provides to observe all colors necessary for display technologies in a very small potential range. The material is a derivative of benzotriazole containing donor acceptor type conducting polymer which is soluble, fluorescent and can be used in LEDs, solar cells, electrochromic devices, smart windows and many other technologies.
• Thieno[3,2-b]thiophene as π-bridge at different acceptor systems for electrochromic applications
  作者：Sinem Toksabay、Serife O. Hacioglu、Naime A. Unlu、Ali Cirpan、Levent Toppare

  DOI：10.1016/j.polymer.2014.05.029

  日期：2014.6

  Benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene are the units preferred in conducting polymers due to their electrochemical properties. There are no reports in the literature on polymers containing both moieties. In this study, novel benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene based monomers; 4-(3a,6a-dihydrothieno[3,2-b]thiophen-2-y1)-7-(thieno[3,2-b]thiophenyl) benzo[c][1,2,51selenadiazole (BSeTT) and 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromo-2,3dihydroquinoxaline (QTT) were synthesized via Stille Coupling and polymerized electrochemically. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV Vis NIR spectroscopy. Spectroelectrochemistry analysis of PBSeTT revealed an electronic transition at 525 nm corresponding to pi-pi* transition with a band gap of 0.93 eV whereas PQTT revealed electronic transitions at 440 and 600 nm corresponding to pi-pi*transitions with a band gap of 1.30 eV. Electrochromic investigations showed that PBSeTT has gray color PQTT switching between green and gray. Switching time of the polymers was evaluated by a kinetic study upon measuring the percent transmittance (%T) at the maximum contrast point. (C) 2014 Elsevier Ltd. All rights reserved.