4,4'-bis(2-ethylhexyloxy)-2,2'-bithiophene-3,3'-dicarbonitrile | 1276689-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,4'-bis(2-ethylhexyloxy)-2,2'-bithiophene-3,3'-dicarbonitrile
• 英文别名: 2,2'-bis(3-cyano-4-(2-ethylhexyloxy)thiophene)；2-[3-Cyano-4-(2-ethylhexoxy)thiophen-2-yl]-4-(2-ethylhexoxy)thiophene-3-carbonitrile；2-[3-cyano-4-(2-ethylhexoxy)thiophen-2-yl]-4-(2-ethylhexoxy)thiophene-3-carbonitrile
• CAS: 1276689-16-7
• 化学式: C₂₆H₃₆N₂O₂S₂
• 分子量: 472.716
• InChiKey: BGLBEUDJXDFJCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-bis(2-ethylhexyloxy)-2,2'-bithiophene-3,3'-dicarbonitrile 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 30.67h， 生成 2-[3-Cyano-4-(2-ethylhexoxy)-5-thieno[3,2-b][1]benzothiol-2-ylthiophen-2-yl]-4-(2-ethylhexoxy)-5-thieno[3,2-b][1]benzothiol-2-ylthiophene-3-carbonitrile
  参考文献：
  名称：

  Synthesis and Electronic Properties of D–A–D Triads Based on 3-Alkoxy-4-cyanothiophene and Benzothienothiophene Blocks

  摘要：

  3-Alkoxy-4-cyanothiophene units are used as building block for the synthesis of conjugated donor acceptor donor (D-A-D) triads. The donor part consists of benzothienothiophene end groups associated with the alkoxy groups of the 3-alkoxy-4-cyanothiophene, while the central acceptor part is formed by combining the electron-withdrawing cyano group with thiophene or benzothiadiazole units.

  DOI：

  10.1021/jo202412t
• 作为产物：
  描述：

  4-((2-乙基己基)氧基)噻吩-3-甲腈 在 正丁基锂 、 三甲基氯化锡 、 碘 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以32%的产率得到4,4'-bis(2-ethylhexyloxy)-2,2'-bithiophene-3,3'-dicarbonitrile
  参考文献：
  名称：

  Synthesis and Electronic Properties of D–A–D Triads Based on 3-Alkoxy-4-cyanothiophene and Benzothienothiophene Blocks

  摘要：

  3-Alkoxy-4-cyanothiophene units are used as building block for the synthesis of conjugated donor acceptor donor (D-A-D) triads. The donor part consists of benzothienothiophene end groups associated with the alkoxy groups of the 3-alkoxy-4-cyanothiophene, while the central acceptor part is formed by combining the electron-withdrawing cyano group with thiophene or benzothiadiazole units.

  DOI：

  10.1021/jo202412t

文献信息

• A donor–acceptor–donor (D–A–D) molecule based on 3-alkoxy-4-cyanothiophene and dithienopyrrole units as active material for organic solar cells
  作者：Ali Yassin、Gurunathan Savitha、Philippe Leriche、Pierre Frère、Jean Roncali

  DOI：10.1039/c2nj40513j

  日期：——

  A symmetrical donor–acceptor–donor D–A–D system built by connecting two dithienopyrrole donor blocks to a central electron acceptor obtained by dimerization of 3-alkoxy-4-cyano-thiophene has been synthesized and characterized. The compound combines a high photoluminescence efficiency with a broad absorption spectrum in the solid state and a band gap of 1.70 eV. A preliminary evaluation of the potentialities of this type of compound as donor material in bulk heterojunction solar cells using PC61BM as electron acceptor is presented.

  通过将两个二噻吩并吡咯供体块连接到由3-烷氧基-4-氰基噻吩二聚化得到的中心电子受体，合成并表征了对称供体-受体-供体D-A-D系统。该化合物在固态下具有高光致发光效率和宽吸收光谱，带隙为1.70 eV。本文初步评估了这种化合物作为使用PC61BM作为电子受体的块状异质结太阳能电池中的供体材料的潜力。
• Facile Synthesis of 3-Alkoxy-4-cyanothiophenes As New Building Blocks for Donor−Acceptor Conjugated Systems
  作者：Noémie Hergué、Charlotte Mallet、Gurunathan Savitha、Magali Allain、Pierre Frère、Jean Roncali

  DOI：10.1021/ol200296j

  日期：2011.4.1

  3-Alkoxy-4-cyanothiophenes are efficiently synthesized in two steps from the readily available 4-cyano-3-oxotetrahydrothiophene. Regioisomers of bithiophene derivatives are easily synthesized by playing on the strong electronic dissymmetry of the thiophene ring induced by the alkoxy and cyano groups.
• Synthesis and Electronic Properties of D–A–D Triads Based on 3-Alkoxy-4-cyanothiophene and Benzothienothiophene Blocks
  作者：Charlotte Mallet、Gurunathan Savitha、Magali Allain、Václav Kozmík、Jiří Svoboda、Pierre Frère、Jean Roncali

  DOI：10.1021/jo202412t

  日期：2012.2.17

  3-Alkoxy-4-cyanothiophene units are used as building block for the synthesis of conjugated donor acceptor donor (D-A-D) triads. The donor part consists of benzothienothiophene end groups associated with the alkoxy groups of the 3-alkoxy-4-cyanothiophene, while the central acceptor part is formed by combining the electron-withdrawing cyano group with thiophene or benzothiadiazole units.