5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophene]-5-carbaldehyde | 1421238-78-9

• 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: 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophene]-5-carbaldehyde
• 英文别名: 5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[2,2']bithiophenyl-5-carboxaldehyde；5-formyl-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene；5’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2’-bithiophene-5-carbaldehyde；5-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 1421238-78-9
• 化学式: C₁₅H₁₇BO₃S₂
• 分子量: 320.241
• InChiKey: GYVOXEOJJKSXKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘三苯胺 、 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophene]-5-carbaldehyde 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 以58%的产率得到5'-(4-(二苯氨基)苯基)-[2,2'-联噻吩]-5-甲醛
  参考文献：
  名称：

  A new route towards fluorescent organic nanoparticles with red-shifted emission and increased colloidal stability

  摘要：

  Suzuki-Miyaura cross-coupling reaction with a new boron reagent has been used to conveniently and efficiently synthetize a dipolar chromophore having an elongated pi-conjugated system (i.e., bithiophene based), which displays a red-shifted emission while maintaining fluorescence. Bright orange emitting FONs made from this 'naked' dipole have been easily prepared and studied. Very interestingly, these FONs with red-shifted emission combine markedly enhanced colloidal and structural stability in water with giant one- and two-photon brightness. As such, they hold promises as fluorescent probes for bioimaging. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.01.032
• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophene]-5-carbaldehyde
  参考文献：
  名称：

  A new route towards fluorescent organic nanoparticles with red-shifted emission and increased colloidal stability

  摘要：

  Suzuki-Miyaura cross-coupling reaction with a new boron reagent has been used to conveniently and efficiently synthetize a dipolar chromophore having an elongated pi-conjugated system (i.e., bithiophene based), which displays a red-shifted emission while maintaining fluorescence. Bright orange emitting FONs made from this 'naked' dipole have been easily prepared and studied. Very interestingly, these FONs with red-shifted emission combine markedly enhanced colloidal and structural stability in water with giant one- and two-photon brightness. As such, they hold promises as fluorescent probes for bioimaging. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.01.032

文献信息

• Synthesis and Investigation of Solar-Cell Photosensitizers Having a Fluorazone Backbone
  作者：Béla Mátravölgyi、Tamás Hergert、Angelika Thurner、Bálint Varga、Nicola Sangiorgi、Riccardo Bendoni、Lorenzo Zani、Gianna Reginato、Massimo Calamante、Adalgisa Sinicropi、Alessandra Sanson、Ferenc Faigl、Alessandro Mordini

  DOI：10.1002/ejoc.201601622

  日期：2017.4.10

  fully conjugated, 2,7-disubstituted fluorazone (9H-pyrrolo[1,2-a]indol-9-one) derivatives was developed, comprising Elming-Clauson-Kaas type pyrrole formation, POCl3-mediated ring closure, selective halogenation and elongation of the conjugate backbone via cross-coupling reactions. As a proof of principle, such methodology was used to prepare for the first time two organic D-π-A dyes containing the fluorazone

  开发了用于制备完全共轭的 2,7-二取代氟腙（9H-吡咯并[1,2-a]indol-9-one）衍生物的合成序列，包括 Elming-Clauson-Kaas 型吡咯形成，POCl3 介导通过交叉偶联反应实现共轭主链的闭环、选择性卤化和延伸。作为原理证明，这种方法首次用于制备两种含有氟腙部分的有机 D-π-A 染料。当吸附在纳米晶 TiO2 上时，新化合物显示出广泛的可见光吸收，并且电化学特性与它们在染料敏化太阳能电池中用作光敏剂相兼容。用氟腙染料制造的小型光伏器件产生的功率转换效率在 2.1-2.4% 范围内，相当于大约
• Biindole-based double D–π–A branched organic dyes for efficient dye-sensitized solar cells
  作者：Xing Qian、Huan-Huan Gao、Yi-Zhou Zhu、Lin Lu、Jian-Yu Zheng

  DOI：10.1039/c4ra12888e

  日期：——

  Novel biindole-based double D–π–A branched organic dyes have been designed and synthesized for dye-sensitized solar cells.

  基于新型双吲哚基双D-π-A分支有机染料已经被设计并合成用于染料敏化太阳能电池。
• 新規化合物及びそれを含む光電変換素子
  申请人：公立大学法人首都大学東京

  公开号：JP2016185911A

  公开（公告）日：2016-10-27

  【課題】増感色素として広範囲の可視光を比較的効率的に電気に変換可能な新規化合物、及びこれを含む光電変換素子の提供。【解決手段】下式（１）で表される化合物。（ｍは１乃至５の整数；ｌ及びｎは各々独立に０乃至６の整数；ｊは０〜３の整数；Ｘ1及びＸ2はＨ、カルボキシル基若しくはその塩、水酸基若しくはその塩、リン酸基若しくはその塩等；Ｑ1及びＱ2はＯ、Ｓ等；Ａ1〜Ａ8はＨ、置換若しくは非置換脂肪族炭化水素残基、シアノ基、ハロゲン原子等；Ｒ２はホウ素-ピロメテン構造を有す基）【選択図】なし

  【问题】提供一种能够相对高效地将广泛的可见光转换为电能的新型化合物作为增感色素，以及包含该化合物的光电转换元件。 【解决方案】化合物由下式（1）表示（其中，m为1至5的整数；l和n各自独立地为0至6的整数；j为0至3的整数；X1和X2为H、羧基或其盐、水氧基或其盐、磷酸基或其盐等；Q1和Q2为O、S等；A1~A8为H、取代或未取代的脂肪族烷基残基、氰基、卤原子等；R2为具有硼-吡咯烷结构的基）【选图】无。
• Modified Triphenylamine-Dicyanovinyl-Based Donor-Acceptor Dyes with Enhanced Power Conversion Efficiency of p-Type Dye-Sensitized Solar Cells
  作者：Linna Zhu、Hongbin Yang、Cheng Zhong、Chang Ming Li

  DOI：10.1002/asia.201200402

  日期：2012.12

  To dye for: Two new dyes are synthesized by structural modifications of one of the best dyes for NiO p‐type dye‐sensitized solar cells, which is based on a triphenylamine–dicyanovinyl donor–acceptor system. An additional thiophene unit near the anchoring group can greatly retard charge recombination while enhancing the absorption coefficient to significantly improve the photoconversion efficiency by

  用于染色：通过对NiO p型染料敏化太阳能电池的最佳染料之一进行结构修饰，合成了两种新染料，该染料基于三苯胺-双氰基乙烯基供体-受体体系。锚定基团附近的另一个噻吩单元可以大大延迟电荷重组，同时提高吸收系数，从而将光转换效率显着提高50％。
• Tetraindole-based saddle-shaped organic dyes for efficient dye-sensitized solar cells
  作者：Xing Qian、Huan-Huan Gao、Yi-Zhou Zhu、Bin Pan、Jian-Yu Zheng

  DOI：10.1016/j.dyepig.2015.05.015

  日期：2015.10

  Two new metal-free organic dyes which consist of a saddle-shaped tetraindole donor, a cyanoacrylic acid acceptor/anchoring group and a thiophene or bithiophene it-bridge have been successfully designed and synthesized for dye-sensitized solar cells. The two dyes showed good photoelectric properties, and the saddle-shaped structure of the tetraindole unit was found to be favorable for preventing intermolecular aggregation and enhancing the photovoltage. The two tetraindole-based dyes exhibited good photovoltaic performances in solar cells. An efficiency up to 6.46% with a high open-circuit photovoltage of 762 mV was achieved for the dye JY15 with a 2,2`-bithiophene moiety as the pi-bridge using an iodine electrolyte under standard conditions. (C) 2015 Elsevier Ltd. All rights reserved.