5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2,2'-bithiophene-5-carbaldehyde | 922737-38-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2,2'-bithiophene-5-carbaldehyde
• 英文别名: 5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2,2'-bithophene-5-carbaldehyde；5'-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-2,2'-bithiophene-5-carbaldehyde；5-[5-[4-[Bis(9,9-dimethylfluoren-2-yl)amino]phenyl]thiophen-2-yl]thiophene-2-carbaldehyde；5-[5-[4-[bis(9,9-dimethylfluoren-2-yl)amino]phenyl]thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 922737-38-0
• 化学式: C₄₅H₃₅NOS₂
• 分子量: 669.911
• InChiKey: DGLHLXZMIFLYEV-UHFFFAOYSA-N

物化性质

• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2,2'-bithiophene-5-carbaldehyde 在 哌啶 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 5-{5'-[N,N-bis(9,9-dimethylfluoren-2-yl)-4-aminophenyl]-2,2'-bithiophen-5-yl}-2-cyanopenta-2,4-dienoic acid
  参考文献：
  名称：

  Novel conjugated organic dyes containing bis-dimethylfluorenyl amino phenyl thiophene for efficient solar cell

  摘要：

  Two novel organic dyes (JK- 5 and JK- 6) containing bis-dimethylfluorenyl amino phenyl thiophene and additional methine unit are synthesized. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using these dyes. A solar-to-electric conversion efficiency of 5.12% and 4.78% is achieved with JK- 5 and JK- 6, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.061
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 2-[N,N-bis(9,9-dimethylfluoren-2-yl)aminophenyl]-5,5'-bithienyl 在 三氯氧磷 作用下， 以82%的产率得到5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2,2'-bithiophene-5-carbaldehyde
  参考文献：
  名称：

  用于太阳能电池应用的有机敏化剂的分子工程

  摘要：

  在分子水平上设计并合成了包含供体、电子传导和锚定基团的新型有机敏化剂。功能化的不对称有机敏化剂 3-{5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) 和 3 -{5'-[N,N-双(9,9-二甲基芴-2-基)苯基]-2,2'-双噻吩-5-基}-2-氰基-丙烯酸(JK-2)，在锚定在 TiO2 薄膜上，表现出前所未有的入射光子电流转换效率为 91%。使用含有 0.6 M-甲基-N-丁基咪唑鎓碘化物、0.04 M 碘、0.025 M LiI、0.05 M 硫氰酸胍和 0.28 M 叔丁基吡啶的 15/85 (v/v) 电解液的光伏数据戊腈和乙腈的混合物显示短路光电流密度为 14.0 +/- 0.2 mA/cm2，753 +/- 10 mV 的开路电压和 0.76 +/-

  DOI：

  10.1021/ja066376f

文献信息

• Synthesis and Characterization of New Push-Pull Chromophores Containing BF₂-Azopyrrole Derivatives
  作者：HayeMin Ko

  DOI：10.5012/jkcs.2016.60.1.21

  日期：2016.2.20

  Novel push-pull chromophores containing 5'-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)aniline (bisDMFA) as a donor and phenylazo-methylpyrrolyl-boron difluoride (PhAPy-BF2) as an acceptor were designed and synthesized by the Kno- evenagel condensation reaction for organic solar cells. Various electron withdrawing moieties were effectively introduced using 2,4-dimethyl-1H-pyrrole to afford new asymmetric

  新型推挽发色团，其包含5'-（4-（双（9,9-二甲基-9H-芴-2-基）苯胺）（bisDMFA）作为供体和苯基偶氮-甲基吡咯基-硼二氟化硼（PhAPy-BF2）通过Knoevenagel缩合反应设计并合成了用于有机太阳能电池的受体，利用2,4-二甲基-1H-吡咯有效地引入了各种吸电子基团，得到了具有紫外可见光谱特征的新型不对称BF2-偶氮吡咯分子。 -镜检和循环伏安法测量。
• Molecular engineering of push-pull chromophore for efficient bulk-heterojunction morphology in solution processed small molecule organic photovoltaics
  作者：Haye Min Ko、Hyunbong Choi、Sanghyun Paek、Kyungjun Kim、Kihyung Song、Jae Kwan Lee、Jaejung Ko

  DOI：10.1039/c1jm10667h

  日期：——

  The synthesis and characterization of new push-pull chromophores, bisDMFA-diTh-CA, bisDMFA-diTh-MMN, and bisDMFA-diTh-MIMN from 5′-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)aniline (bisDMFA) electron donating, dithiophene bridging, and various electron withdrawing moieties, cyanoacrylic acid (CA), methylene malononitrile (MMN), and methylene indenylidene malononitrile (MIMN), were demonstrated for efficient solution processed BHJ solar cells. The photophysical properties, the hole mobilities from the space charge limitation of current (SCLC) J-V characteristics, and surface morphologies of these materials/PCBM bulk-heterojunction films were also investigated. The best power conversion efficiency of 3.66% (±0.12) with Jsc = 11.82 mA/cm2, FF = 0.35, and Voc = 0.90 V was observed in the BHJ film fabricated with the bisDMFA-diTh-MMN/C71-PCBM composite with 3% 1-chloronaphthalene (CN), which is an efficiency ∼82% and ∼49% higher than before and after post-annealing without treatment of CN, respectively.

  从 5′-(4-(双(9,9-二甲基-9H-芴-2-基)苯胺 (bisDMFA) 电子捐赠、二噻吩桥接、和亚甲基丙二腈（MMN），以及亚甲基亚茚基丙二腈（MIMN）等各种电子汲取分子，被证明可用于高效的溶液处理 BHJ 太阳能电池。此外，还研究了这些材料/PCBM 体外异质结薄膜的光物理特性、空间电荷限流（SCLC）J-V 特性中的空穴迁移率以及表面形态。使用含有 3% 1-氯萘 (CN) 的双DMFA-diTh-MMN/C71-PCBM 复合材料制造的 BHJ 薄膜观察到最佳功率转换效率为 3.66% (±0.12)，Jsc = 11.82 mA/cm2，FF = 0.35，Voc = 0.90 V。
• Molecular Engineering of Organic Sensitizers for Solar Cell Applications
  作者：Sanghoon Kim、Jae Kwan Lee、Sang Ook Kang、Jaejung Ko、J.-H. Yum、Simona Fantacci、Filippo De Angelis、D. Di Censo、Md. K. Nazeeruddin、Michael Grätzel

  DOI：10.1021/ja066376f

  日期：2006.12.1

  Novel organic sensitizers comprising donor, electron-conducting, and anchoring groups were engineered at molecular level and synthesized. The functionalized unsymmetrical organic sensitizers 3-5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) and 3-5'-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-2,2'-bisthiophene-5-yl}-2-cyano-acrylic acid (JK-2), upon anchoring

  在分子水平上设计并合成了包含供体、电子传导和锚定基团的新型有机敏化剂。功能化的不对称有机敏化剂 3-5-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-thiophene-2-yl}-2-cyano-acrylic acid (JK-1) 和 3 -5'-[N,N-双(9,9-二甲基芴-2-基)苯基]-2,2'-双噻吩-5-基}-2-氰基-丙烯酸(JK-2)，在锚定在 TiO2 薄膜上，表现出前所未有的入射光子电流转换效率为 91%。使用含有 0.6 M-甲基-N-丁基咪唑鎓碘化物、0.04 M 碘、0.025 M LiI、0.05 M 硫氰酸胍和 0.28 M 叔丁基吡啶的 15/85 (v/v) 电解液的光伏数据戊腈和乙腈的混合物显示短路光电流密度为 14.0 +/- 0.2 mA/cm2，753 +/- 10 mV 的开路电压和 0.76 +/-
• Synthesis and characterization of push–pull organic semiconductors with various acceptors for solution-processed small molecule organic solar cells
  作者：Nara Cho、Jooyoung Kim、Kihyung Song、Jae Kwan Lee、Jaejung Ko

  DOI：10.1016/j.tet.2012.03.061

  日期：2012.5

  New efficient push-pull organic semiconductors comprising of the bis(9,9-dimethyl-9H-fluoren-2-yl) aniline (bisDMFA) donor and the various acceptors such as NO2, DCBP, and TCF, which were linked with bithiophene or vinyl bithiophene pi-conjugation bridges, were synthesized, and their photovoltaic characteristics were investigated in solution-processed small molecule organic solar cells (SMOSCs). The intramolecular charge transfers of these materials were effectively appeared in between bisDMFA donor and acceptors, depending on the electron-withdrawing strength of acceptors. The organic semiconductors having NO2 and DCBP acceptors exhibited the most efficient photovoltaic performance, showing power conversion efficiency (PCE) of 1.98% (+/- 0.17) and 2.01% (+/- 0.21), respectively. When the TiOx thin layer was treated on photoactive layer, the organic semiconductor having NO2 showed the best PCE of 2.70% with short circuit current of 8.19 mA/cm(2), fill factor of 0.40, and open circuit voltage of 0.83 V in SMOSC devices. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel conjugated organic dyes containing bis-dimethylfluorenyl amino phenyl thiophene for efficient solar cell
  作者：Sanghoon Kim、Hyunbong Choi、Duckhyun Kim、Kihyung Song、Sang Ook Kang、Jaejung Ko

  DOI：10.1016/j.tet.2007.06.061

  日期：2007.9

  Two novel organic dyes (JK- 5 and JK- 6) containing bis-dimethylfluorenyl amino phenyl thiophene and additional methine unit are synthesized. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using these dyes. A solar-to-electric conversion efficiency of 5.12% and 4.78% is achieved with JK- 5 and JK- 6, respectively. (c) 2007 Elsevier Ltd. All rights reserved.