(9-butyl-9H-carbazol-3-yl)boronic acid | 905564-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (9-butyl-9H-carbazol-3-yl)boronic acid
• 英文别名: 9-butylcarbazol-3-ylboronic acid；9-butyl-9H-carbazol-3-yl-3-boronic acid；(9-butylcarbazol-3-yl)boronic acid
• CAS: 905564-60-5
• 化学式: C₁₆H₁₈BNO₂
• 分子量: 267.135
• InChiKey: BHPFJSSEAGZKBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9-butyl-9H-carbazol-3-yl)boronic acid 在 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 68.08h， 生成
  参考文献：
  名称：

  Optimizing the photovoltaic performance of thiocyanate-free ruthenium photosensitizers by structural modification of C^N cyclometalating ligand in dye-sensitized solar cells

  摘要：

  Five new thiocyanate-free ruthenium(II) complexes with different electron-donating functionalized cyclometalating ligands C<^>N were synthesized, characterized and applied as photosensitizers in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical, thermal and photovoltaic properties have been investigated and density functional theory (DFT) calculations have been carried out on these dyes. These dyes exhibit good thermal stability with the onset decomposition temperature at 5% weight-loss (T-d) of around 330 degrees C. The DSSC device using the Ru(II) dye with the 9-tolylcarbazole chromophore exhibited the highest power conversion efficiency (eta) up to 3.39%, with a short-circuit photocurrent density (J(sc)) of 8.06 mA cm(-2), an open-circuit photovoltage (V-oc) of 0.62 V and a high fill factor (ff) of 0.68 under illumination of an AM 1.5 solar cell simulator. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.04.059
• 作为产物：
  描述：

  咔唑 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (9-butyl-9H-carbazol-3-yl)boronic acid
  参考文献：
  名称：

  功能性树枝状低聚噻吩的合成及光电性能

  摘要：

  具有空穴传输咔唑作为外围取代基和吸电子双氰基乙烯基核心基团（即DCT（n）-DCN）的新型p型和低带隙功能树突性低聚噻吩，其中n = 1或2对于溶液可加工光伏（PV）应用程序已综合。通过将给电子的咔唑表面官能化的部分与双氰基乙烯基核心基团偶联，这些功能性树突状低聚噻吩薄膜的光学带隙大大降低至1.74 eV，具有很强的光谱展宽和大约5.5 eV的高电离电势（通过紫外光电子测定）光谱学。由这些树枝状聚合物与PC 71混合制成的块状异质结PV电池在退火设备中，作为受体的BM在（V oc）= 0.93 V的开路电压下显示出高达1.64％的功率转换效率。我们已经证明，可以通过将官能团结合到树枝状分子的外围和核心中来获得/调节树枝状寡聚噻吩的理想的分子和PV性质。此外，这些功能性树状寡聚噻吩即使在低树突状生成时也表现出优越的功能特性，与可溶液处理的本体异质结光伏电池的ap型，低带隙半导体相比，未取代的

  DOI：

  10.1002/pola.24613

文献信息

• Dye-sensitized solar cells based on organic dyes with naphtho[2,1-b:3,4-b′]dithiophene as the conjugated linker
  作者：Xiaoxu Wang、Lei Guo、Ping Fang Xia、Fan Zheng、Man Shing Wong、Zhengtao Zhu

  DOI：10.1039/c3ta12901b

  日期：——

  Naphtho[2,1-b:3,4-b′]dithiophene is used for the first time as the π-spacer for metal-free organic dyes in dye-sensitized solar cells (DSSCs). Four new donor–(π-spacer)–acceptor organic dyes using triarylamine or carbazole as the electron-donating group, cyanoacrylic acid as the electron-withdrawing anchoring moiety, and naphtho[2,1-b:3,4-b′]dithiophene as the linker were synthesized. The absorption, electrochemical, and photovoltaic properties of the dyes were investigated. DSSCs based on these dyes as sensitizers had efficiencies ranging from 3.98% to 4.60%. The highest efficiency was 4.60 ± 0.16% with a Jsc of 10.8 ± 0.4 mA cm−2, a Voc of 657 ± 5 mV, and a fill factor of 64.0 ± 0.2% under 100 mW AM 1.5 irradiation. The incident photon-to-current efficiency (IPCE) measurement showed that these dyes had high quantum efficiency over the visible range, and the long π-spacer of the molecule resulted in broader IPCE at long wavelength and high Jsc. Photovoltage transient was used to understand the electron recombination and the trends of the photovoltaic parameters (e.g. Voc and efficiency) of the DSSCs based on these organic dyes.

  首次采用萘并[2,1-b:3,4-b']二噻吩作为染料敏化太阳能电池（DSSCs）中不含金属有机染料的π-桥连单元。合成了四种新型供体-（π-桥连单元）-受体有机染料，分别使用三芳胺或咔唑作为电子供体基团，氰基丙烯酸作为电子吸引锚定部分，萘并[2,1-b:3,4-b']二噻吩作为连接单元。研究了这些染料的吸收、电化学和光伏特性。基于这些染料作为敏化剂的DSSCs效率范围从3.98%到4.60%。在100 mW AM 1.5辐照下，最高效率为4.60 ± 0.16%，对应的Jsc为10.8 ± 0.4 mA cm⁻²，Voc为657 ± 5 mV，填充因子为64.0 ± 0.2%。入射光子-电流效率（IPCE）测量显示，这些染料在可见光区域具有高量子效率，分子的长π-桥连单元导致在长波长处IPCE更宽，Jsc更高。使用光电压瞬态来理解基于这些有机染料的DSSCs的电子复合和光伏参数（如Voc和效率）的趋势。
• Jacket-like structure of donor-acceptor chromophores-based conducting polymers for photovoltaic cell applications
  作者：Yi-Lung Yang、Yi-Huan Lee、Chun-Jie Chang、Ang-Jhih Lu、Wei-Chun Hsu、Leeyih Wang、Man-Kit Leung、Chi-An Dai

  DOI：10.1002/pola.23921

  日期：2010.4.1

  Solar cells made from PCPQT/PCBM bulk heterojunction show a high open‐circuit voltage, Voc of ∼0.75 V, which is significantly higher than that of a solar cell made from conventional poly(3‐hexyl thiophene)/PCBM as the active polymer PCPQT has lower HOMO level. Further improvements are anticipated through a rational design of the new low band‐gap and the structurally two‐dimensional donor–acceptor conducting

  通过Stille偶联聚合，设计，合成和研究了一系列具有咔唑的空穴传输部分作为侧链（PCPQT）的可溶性受体/供体喹喔啉/噻吩交替导电聚合物。对具有低多分散性的不同分子量的电荷转移型PCPQT进行紫外可见测量，随着链长的增加，其最大吸收值从530 nm迁移到630 nm（M n：从1100到19,200）。PCPQT的HOMO和LUMO能级可以根据循环伏安法测量分别确定为-5.36和-3.59 eV。由PCPQT / PCBM制成的太阳能电池本体异质结显示出高的开路电压，约0.75 V的V oc，这明显高于由常规聚（3-己基噻吩）/ PCBM制成的太阳能电池的电压，因为活性聚合物PCPQT的HOMO含量较低。通过合理设计新的低带隙和结构​​二维的施主-受主导电聚合物，可以期待进一步的改进。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem
• Synthesis and characterization of graft polystyrenes with para-substituted π-conjugated oligo(carbazole) and oligo(carbazole-thiophene) moieties for organic field-effect transistors
  作者：Gung-Pei Chang、Ching-Nan Chuang、Jong-Yih Lee、Yung-Shen Chang、Man-kit Leung、Kuo-Huang Hsieh

  DOI：10.1016/j.polymer.2013.04.002

  日期：2013.6

  polymers. The thermal, optical, and electrochemical properties of these studied monomers and polymers were fully characterized for studying the relationships of the structures to the properties. The field-effect characteristics of the polymers were also studied, a highest hole mobility on the order of 1.1 × 10−3 cm2V−1s−1 was obtained with PStCzT2Cz. The morphology of the polymeric active layers was also

  在这项研究中，制备了两种基于联咔唑和咔唑-联噻吩-咔唑的苯乙烯衍生物单体（StCz2和StCzT2Cz），并进一步自由基聚合（PStCz2和PStCzT2Cz）以形成接枝π共轭聚合物。这些研究的单体和聚合物的热，光学和电化学性质已得到充分表征，以研究结构与性质之间的关系。还研究了聚合物的场效应特性，使用PStCzT2Cz获得了最高的空穴迁移率，约为1.1×10 -3 cm 2 V -1 s -1。还通过X射线衍射和原子力显微镜研究了聚合物活性层的形态，以实现结构与电特性的关系。
• Novel branched coumarin dyes for dye-sensitized solar cells: significant improvement in photovoltaic performance by simple structure modification
  作者：Bo Liu、Ran Wang、Weijun Mi、Xiaoyan Li、Haitao Yu

  DOI：10.1039/c2jm32333h

  日期：——

  The construction of branched coumarin dyes based on a 2D-π-A system is focused to optimize the light-harvesting capability and enhance the photovoltaic performance. Three novel coumarin dyes, coded as MS-C, MS-F, and MS-M, respectively, were obtained by incorporating different units (carbazole, fluorene and methyl groups) with different molecular volume and degrees of electron-donating capability into the π-conjugation linker. Through molecular engineering, their light-harvesting capabilities, energy levels and photovoltaic performance were studied systematically. As expected, with the additional donor, especially utilizing strong electron-donating carbazole unit, the IPCE action spectrum of MS-C keeps a high plateau from 390 nm to 580 nm with nearly unity values. Along with the improvement of IPCE, the Jsc values of the three dyes were increased by 77% from 7.61 (MS-M) to 13.47 mA cm−2 (MS-C). Using DCA as the co-adsorbed material, the Jsc of MS-M was increased while these values were decreased in the cases of branched MS-C and MS-F. This means that the twist structure arising from the branched donors could prevent π-aggregation effectively. More importantly, the Voc was also improved significantly by introducing the additional donor. While the branched 2D-π-A system was constructed, the Voc was sharply increased from 508 (MS-M) to 610 mV (MS-C). Comprehensively, a more than 100% enhancement in overall conversion efficiency (5.53%) was realized by branched MS-C compared to the linear MS-M (2.74%). Although the overall conversion efficiencies of these dyes are not very high, these results will still afford significant value for future development of efficient coumarin sensitizers with high open-circuit voltage.

  基于2D-π-A系统的分支香豆素染料的构建旨在优化光捕获能力并提升光伏性能。通过将不同单元（卡巴佐、氟烯和甲基）与具有不同分子体积和电子供给能力的π共轭连结体结合，获得了三种新型香豆素染料，分别编码为MS-C、MS-F和MS-M。通过分子工程，系统性地研究了它们的光捕获能力、能级和光伏性能。如预期所示，随着额外供体的引入，特别是利用强电子供体卡巴佐单元，MS-C的IPCE作用谱在390 nm至580 nm范围内保持高平台，值接近于1。随着IPCE的提高，三种染料的短路电流密度（Jsc）值从7.61 mA cm−2（MS-M）增加到13.47 mA cm−2（MS-C），增加幅度达到77%。使用DCA作为共吸附材料时，MS-M的Jsc有所增加，而分支的MS-C和MS-F的值则有所下降。这意味着源于分支供体的扭曲结构可以有效防止π聚集。更重要的是，通过引入额外的供体，开路电压（Voc）得到了显著提升。当构建分支的2D-π-A系统时，Voc从508 mV（MS-M）急剧增加到610 mV（MS-C）。综合来看，与线性MS-M（2.74%）相比，分支的MS-C在总体转换效率上实现了超过100%的提升（5.53%）。尽管这些染料的总体转换效率并不非常高，但这些结果仍将对未来开发高开路电压的高效香豆素敏化剂提供重要价值。
• The synthesis and optical properties of benzothiazole-based derivatives with various π-electron donors as novel bipolar fluorescent compounds
  作者：Haiying Wang、Gang Chen、Xiaoping Xu、Hua Chen、Shunjun Ji

  DOI：10.1016/j.dyepig.2010.01.010

  日期：2010.8

  Novel bipolar benzothiazole-based derivatives with various π-electron donors were synthesized and characterized using 1H and 13C NMR and mass spectrometry; their thermal, optical and electrochemical properties were also investigated. Optoelectronic properties are reported and discussed in terms of the distribution of the highest occupied molecular orbital and the lowest unoccupied molecular orbital

  合成了具有各种π电子给体的新型双极苯并噻唑基衍生物，并使用1 H和13 C NMR和质谱进行了表征；还研究了它们的热，光学和电化学性能。根据最高占据的分子轨道的分布和最低的未占据的分子轨道的分布以及给电子部分和受电子部分之间的共轭途径来报道和讨论光电子性质。这些化合物表现出高的荧光量子产率，理想的HOMO水平和高的热稳定性。使用量子化学计算来研究优化的基态几何形状以及化合物的HOMO和LUMO水平的空间分布。