2,1,3-苯并恶二唑,4,7-双(5-溴-2-噻吩)- | 1007128-65-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 2,1,3-苯并恶二唑,4,7-双(5-溴-2-噻吩)-
• 英文名称: 4,7-bis(5-bromothiophen-2-yl)-2,1,3-benzoxadiazole
• 英文别名: 4,7-bis(5-bromo-2-thienyl)-2,1,3-benzoxadiazole；4,7-Bis(5-bromothiophen-2-yl)-2,1,3-benzoxadiazole
• CAS: 1007128-65-5
• 化学式: C₁₄H₆Br₂N₂OS₂
• 分子量: 442.154
• InChiKey: PRWKRKOJCUBXTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,1,3-苯并恶二唑,4,7-双(5-溴-2-噻吩)- 、 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-[4-(N,N-diphenylamino)phenyl]-acrylonitrile 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 以56%的产率得到4,7-bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole
  参考文献：
  名称：

  D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties

  摘要：

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.001
• 作为产物：
  描述：

  甲基硝基苯 在 吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hypochlorite 、 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 溴 、 铁粉 、 sulfur 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇 、 邻二氯苯 为溶剂， 生成 2,1,3-苯并恶二唑,4,7-双(5-溴-2-噻吩)-
  参考文献：
  名称：

  D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties

  摘要：

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.001

文献信息

• Luminescent solar concentrator comprising disubstituted benzoheterodiazole compounds
  申请人：ENI S.p.A.

  公开号：US10312395B2

  公开（公告）日：2019-06-04

  Luminescent solar concentrator (LSC) comprising at least one disubstituted benzoheterodiazole compound of general formula (I), in which: —Z represents a sulfur atom, an oxygen atom, a selenium atom; or an NR6 group in which R6 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or from optionally substituted aryl groups; —R1, R2 and R3, which are the same or different, represent a hydrogen atom; or are selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted linear or branched C1-C20, preferably C1-C8, alkoxyl groups, optionally substituted phenoxyl groups, or —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or is a cyano group, provided that when the substituents R1 represents a hydrogen atom, at least one of the substituents R2 and R3 represents an optionally substituted aryl group or an optionally substituted phenoxyl group; —or R1 and R2, can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorus, selenium; —or R2 and R3 can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorus, selenium; —R4 and R5, which are the same or different, represent a hydrogen atom; or are selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted linear or branched C1-C20, preferably C1-C8, alkoxyl groups, —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or is a cyano group; or R4 and R5, can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated, or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, containing one or more heteroatoms such as, for example, sulfur, nitrogen, silicon, phosphorus, selenium.

  发光太阳能聚光器(LSC)，包含至少一种通式(I)的二取代苯并杂二唑化合物，其中：-Z代表硫原子、氧原子、硒原子；或NR6基团，其中R6选自直链或支链C1-C20，优选C1-C8烷基，或选自任选取代的芳基；-R1、R2和R3相同或不同，代表氢原子；或选自直链或支链 C1-C20（最好是 C1-C8）烷基（可选含有杂原子）、可选取代的环烷基、可选取代的芳基、可选取代的直链或支链 C1-C20（最好是 C1-C8）烷氧基、可选取代的苯氧基、或 -COOR7 基团或 -OCOR7 基团，其中 R7 选自直链或支链 C1-C20（最好是 C1-C8）烷基或氰基，条件是当取代基 R1 代表氢原子时，取代基 R2 和 R3 中至少有一个代表任选取代的芳基或任选取代的苯氧基；-或 R1 和 R2 可以任选连接在一起，以便与所连接的碳原子一起形成饱和、不饱和或芳香的环或多环系统，该环含 3 至 14 个碳原子，最好是 4 至 6 个碳原子，任选含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒；-或 R2 和 R3 可以任选连接在一起，从而与所连接的碳原子一起形成饱和、不饱和或芳香的环状或多环状系统，该环状或多环状系统含有 3 至 14 个碳原子，最好是 4 至 6 个碳原子，任选含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒； -R4 和 R5 相同或不同，代表氢原子；或选自直链或支链 C1-C20，优选 C1-C8，烷基，可选含有杂原子，可选取代的环烷基，可选取代的芳基，可选取代的直链或支链 C1-C20，优选 C1-C8，烷氧基，-COOR7 基团或-OCOR7 基团，其中 R7 选自直链或支链 C1-C20，优选 C1-C8，烷基，或氰基；或 R4 和 R5 可以任选连接在一起，从而与所连接的碳原子一起形成一个饱和、不饱和或芳香的环状或多环状体系，该环状或多环状体系含有 3 至 14 个碳原子，最好是 4 至 6 个碳原子，并含有一个或多个杂原子，例如硫、氮、硅、磷、硒。
• Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells
  作者：Nicolas Blouin、Alexandre Michaud、David Gendron、Salem Wakim、Emily Blair、Rodica Neagu-Plesu、Michel Belletête、Gilles Durocher、Ye Tao、Mario Leclerc

  DOI：10.1021/ja0771989

  日期：2008.1.1

  On the basis of theoretical models and calculations, several alternating polymeric structures have been investigated to develop optimized poly(2,7-carbazole) derivatives for solar cell applications. Selected low band gap alternating copolymers have been obtained via a Suzuki coupling reaction. A good correlation between DFT theoretical calculations performed on model compounds and the experimental HOMO, LUMO, and band gap energies of the corresponding polymers has been obtained. This study reveals that the alternating copolymer HOMO energy level is mainly fixed by the carbazole moiety, whereas the LUMO energy level is mainly related to the nature of the electron-withdrawing comonomer. However, solar cell performances are not solely driven by the energy levels of the materials. Clearly, the molecular weight and the overall organization of the polymers are other important key parameters to consider when developing new polymers for solar cells. Preliminary measurements have revealed hole mobilities of about 1 x 10(-3) cm(2).V-1.s(-1) and a power conversion efficiency (PCE) up to 3.6%. Further improvements are anticipated through a rational design of new symmetric low band gap poly(2,7-carbazole) derivatives.
• LUMINESCENT SOLAR CONCENTRATOR COMPRISING DISUBSTITUTED BENZOHETERODIAZOLE COMPOUNDS
  申请人：ENI S.p.A.

  公开号：EP3198658A1

  公开（公告）日：2017-08-02
• D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties
  作者：Shaohang Zeng、Lunxiang Yin、Xueying Jiang、Yanqin Li、Kechang Li

  DOI：10.1016/j.dyepig.2012.04.001

  日期：2012.11

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis5-4-2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis5-4-2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.