4-(2-(3-methylbutan-2-ylidene)hydrazinyl)benzoic acid | 126442-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-(3-methylbutan-2-ylidene)hydrazinyl)benzoic acid
• 英文别名: 4-[2-(3-Methylbutan-2-ylidene)hydrazinyl]benzoic acid；4-[2-(3-methylbutan-2-ylidene)hydrazinyl]benzoic acid
• CAS: 126442-84-0
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: UNDIWHYFUVTYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-(3-methylbutan-2-ylidene)hydrazinyl)benzoic acid 在 三氟化硼乙醚 、 溶剂黄146 作用下， 生成 2,3,3-三甲基-3H-吲哚-5-羧酸
  参考文献：
  名称：

  羧基和醛基改性新型光致变色螺吡喃的合成与研究

  摘要：

  摘要 合成了三种新型光致变色螺吡喃，二氢吲哚片段中含有羧基，[2H]-色烯部分含有醛取代基。使用 1 H 和 13 C NMR、IR 和元素分析研究所得化合物的结构。单晶X射线分析用于细化8'-甲酰基-1,3,3,6'-四甲基-螺[二氢吲哚-2,2'-2H-色烯]-5-羧酸的分子结构。发现在固态下，由于两个相邻分子的羧基之间形成分子间氢键，该化合物的分子以二聚缔合物形式排列。所有螺吡喃都显示出光致变色，开放形式的寿命在 1.5-46.0 s 范围内。

  DOI：

  10.1016/j.molstruc.2019.06.094
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 4-肼基苯甲酸 以 乙醇 为溶剂， 生成 4-(2-(3-methylbutan-2-ylidene)hydrazinyl)benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Photophysical Characterization of Multifunctional Far‐Red Squaraine Dyes for Dye‐Sensitized Solar Cells

  摘要：

  本研究设计了新型远红敏感对称方碱（SQ）染料，旨在通过烷基链末端修饰实现控制染料聚集、促进分子自组装和引入电解质功能等多功能特性。成功合成、表征并详细研究了新设计的无端修饰染料（SQ-5）以及碘（SQ-77）和咪唑（SQ-79）烷基端修饰染料。碘端修饰（SQ-77）导致摩尔消光系数、染料聚集、染料负载和在二氧化钛表面的结合力增强，而咪唑（SQ-79）端修饰后则恰恰相反。在没有碘和酚去氧胆酸的情况下，SQ-77 和 SQ-79 的光伏性能几乎相似，这验证了它们除了作为光敏剂的主要作用外，还分别具有电解质功能和防止染料聚集的多功能作用。以 SQ-5 为敏化剂制造的染料敏化太阳能电池显示出高效的远红外至近红外光敏化和光子收集功能，其短路光电流密度、开路电压和填充因子分别为 11.98 mA cm-2、0.61 V 和 0.57，在模拟太阳辐照下的光电转换效率为 4.2%。

  DOI：

  10.1002/pssa.202300254

文献信息

• Co-sensitization of Organic Dyes for Efficient Dye-Sensitized Solar Cells
  作者：Ming Cheng、Xichuan Yang、Jiajia Li、Fuguo Zhang、Licheng Sun

  DOI：10.1002/cssc.201200655

  日期：2013.1

  efficiency of the sensitized devices (η) was 5.6 % (Jsc=13.3 mA cm−2, Voc=606 mV, and fill factor FF=69.1 %) under 100 mW cm−2 (AM 1.5G) solar irradiation. All of these dyes have very high absorption extinction coefficients and strong absorption in a relatively narrow spectrum range (500–650 nm), so one of our organic dyes was explored as a sensitizer in co‐sensitized solar cells in combination with

  设计并合成了新型花菁染料，其中四氢喹啉衍生物用作电子给体，1-丁基-5-羧基-3，3-二甲基吲哚-1-鎓部分用作电子受体和锚定基团用于染料敏化太阳能电池。这些太阳能电池的光伏性能在很大程度上取决于染料的分子结构，即正己基链和甲氧基单元。引入正己基链引起的电荷复合的延迟导致电子寿命的增加。结果，改善了开路光电压（V oc） 已实现。此外，通过引入甲氧基部分提高了电子注入效率，这导致更高的短路光电流密度（J sc）。在100 mW cm -2下，敏化器件的最高平均效率（η）为5.6％（J sc = 13.3 mA cm -2，V oc = 606 mV，填充系数FF = 69.1％）（AM 1.5G）太阳辐射。所有这些染料都具有很高的吸收消光系数，并且在相对窄的光谱范围（500–650 nm）中具有很强的吸收性，因此我们将其中一种有机染料与其他两种有机染料一起用于共敏化太阳能电池中作为敏化剂现
• Synthesis and study of new photochromic spiropyrans modified with carboxylic and aldehyde substituents
  作者：Ilya V. Ozhogin、Valentina V. Chernyavina、Boris S. Lukyanov、Vasily I. Malay、Irina A. Rostovtseva、Nadezhda I. Makarova、Valery V. Tkachev、Maria B. Lukyanova、Anatoly V. Metelitsa、Sergey M. Aldoshin

  DOI：10.1016/j.molstruc.2019.06.094

  日期：2019.11

  Abstract Three new photochromic spiropyrans containing a carboxylic group in the indoline fragment and an aldehyde substituent in the [2H]-chromene moiety were synthesized. The structure of the compounds obtained was studied using 1 H and 13 C NMR, IR and elemental analysis. Single crystal X-ray analysis was used to refine the molecular structure of 8′-formyl-1,3,3,6′-tetramethyl-spiro[indoline-2,

  摘要 合成了三种新型光致变色螺吡喃，二氢吲哚片段中含有羧基，[2H]-色烯部分含有醛取代基。使用 1 H 和 13 C NMR、IR 和元素分析研究所得化合物的结构。单晶X射线分析用于细化8'-甲酰基-1,3,3,6'-四甲基-螺[二氢吲哚-2,2'-2H-色烯]-5-羧酸的分子结构。发现在固态下，由于两个相邻分子的羧基之间形成分子间氢键，该化合物的分子以二聚缔合物形式排列。所有螺吡喃都显示出光致变色，开放形式的寿命在 1.5-46.0 s 范围内。
• Influence of the anchoring number in a carbazole-based photosensitizer on the photovoltaic performance of p-type NiO dye sensitized solar cells
  作者：Ji Young Park、Bo Youn Jang、Chi Hwan Lee、Hyeong Jin Yun、Jae Hong Kim

  DOI：10.1039/c4ra08271k

  日期：——

  Carbazole dimer enhances the charge injection and reduces the charge recombination to exhibit superior p-type performance of DSSCs.

  Carbazole二聚体增强了电荷注入并减少电荷复合，表现出DSSC的卓越p型性能。
• Efficient Far Red Sensitization of Nanocrystalline TiO₂ Films by an Unsymmetrical Squaraine Dye
  作者：Jun-Ho Yum、Pablo Walter、Simon Huber、Daniel Rentsch、Thomas Geiger、Frank Nüesch、Filippo De Angelis、Michael Grätzel、Mohammad K. Nazeeruddin

  DOI：10.1021/ja0731470

  日期：2007.8.1

  An asymmetric squaraine sensitizer comprising an anchoring group was engineered at the molecular level and synthesized. The functionalized novel squaraine sensitizers upon anchoring onto a TiO2 film exhibit an unprecedented incident photon to current conversion efficiency of 85%. The photovoltaic data of this sensitizer using an electrolyte having composition of 0.6 M M-methyl-N-butyl imidazolium iodide, 0.05 M iodine, 0.1 M LiI, 0.05 M tert-butylpyridine in a 15/85 (v/v) mixture of valeronitrile and acetonitrile revealed a short circuit photocurrent density of 10.5 +/- 0.2 mA/cm(2), an open circuit voltage of 603 +/- 10 mV, and a fill factor of 0.71 +/- 0.02, corresponding to an overall conversion efficiency of 4.50% under standard AM 1.5 sunlight.
• Panchromatic quasi-solid-state squaraine dye sensitized solar cells enhanced by Förster resonance energy transfer of DCM-pyran
  作者：Hyeong Jin Yun、Dae Young Jung、Do Kyoung Lee、Alex K.-Y. Jen、Jae Hong Kim

  DOI：10.1016/j.dyepig.2014.09.034

  日期：2015.2

  The panchromatic operation of quasi-solid state dye sensitized solar cells is one of the most important criteria for enhancing the performance of solar cells. This paper presents a novel strategy for designing efficient panchromatic quasi-solid state dye sensitized solar cells that are enhanced by Forster resonance energy transfer. 4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran is excited by the irradiation of visible light with a short wavelength, and the excited energy is then transferred to a blue organic photosentizer, symmetrically structured squaraine. The addition of 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran to the quasi-solid electrolyte improves the photovoltaic performance of squaraine-sensitized solar cells. The optimized quasi-solid state dye sensitized solar cell exhibits approximately 1.8 times higher overall conversion efficiency than the solar cell without any fluorescence materials. In particular, the photocurrent is enhanced significantly at the absorption wavelength range of 4-(dicyanomethylene)-2-methy1-6-(4-dimethylaminostyryl)-4H-pyran, which means that the panchromatic quasi-solid state dye sensitized solar cell has been designed successfully. (C) 2014 Elsevier Ltd. All rights reserved.