4-(N-methyl-N-hexadecylamino)benzaldehyde | 95808-40-5

• 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-(N-methyl-N-hexadecylamino)benzaldehyde
• 英文别名: 4-(Hexa-decylmethylamino)benzaldehyde；4-[hexadecyl(methyl)amino]benzaldehyde
• CAS: 95808-40-5
• 化学式: C₂₄H₄₁NO
• 分子量: 359.596
• InChiKey: YVOCRVGJQPGGEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(N-methyl-N-hexadecylamino)benzaldehyde 、 3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate 在 哌啶 作用下， 生成 (E)-N-(3-Sulfopropyl)-4-[2-(N-methyl-N-hexadecylaminophenyl)ethenyl]quinolinium
  参考文献：
  名称：

  Photoelectric Conversion Properties of Nanocrystalline TiO₂ Electrodes Sensitized with Hemicyanine Derivatives

  摘要：

  Four hemicyanine derivatives, (E)-N-(3-sulfopropyl-4-[2-(4-dimethylaminophenyl)ethenyl]pyridinium (PS), (E)-N-(3-sulfopropyl-4-[2-(4-dimethylamiophenyl)ethenyl]quinolinium (QS), CE)-N-(3-sulfopropyl-4-[2-(4-N-methyl-N-hexadecylaminophenyl)ethenyl]pyridinium (LPS), and (E)-N-(3-sulfopropyl-4-[2-(4-N-methyl-N-hexadecylaminophenyl)ethenyl]quinolinium (LQS), have been synthesized and characterized with regard to their absorption and electrochemical properties. Photoelectrochemical experiments show that these hemicyanine dyes with D-pi -A systems can yield efficient charge separation under illumination of simulated solar light. Alkyl chain has a remarkable effect on dye adsorbance, incident photon-to-electron conversion efficiency, and overall energy conversion yield. The overall yield is approximately doubled when the methyl group replaces the: long alkyl chain. Action spectrum of QS displayed a broad feature with 33.8% of maximum monochromatic incident photon-to-electron conversion efficiency (IPCE), and a thin-layer sandwich-type solar cell based on nanocrystalline TiO2 film modified with QS produced about 2% of overall yield for the first time, a photovoltaic liquid-junction solar cell based on nanostructured TiO2 electrode sensitized by hemicyanine dyes is reported.

  DOI：

  10.1021/jp001580p

文献信息

• Photocurrent generation of a novel chromoionophore combining D–π–A dye and aza-15-crown-5 ether in LB monolayer films
  作者：Fu-You Li、Lin-Pei Jin、Yan-Yi Huang、Chun-Hui Huang、Jie Zheng、Jian-Quan Guo

  DOI：10.1039/b101189h

  日期：——

  A novel amphiphilic chromoionophore, N-[4-(2,3,6,7,8,9,11,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecin-7-yl)butyl]-4-2-[4-(N-methyl-N-hexadecylamino)phenyl]ethenyl}quinolinium bromide (Crown D), containing a D–π–A styryl dye and an aza-15-crown-5 ether group was synthesized, and successfully transferred onto an indium–tin oxide (ITO) electrode by the Langmuir–Blodgett technique. The effect of different metal cationic subphases on the π–A isotherm of Crown D was investigated. The photoelectric conversion properties of the chromoionophore LB monolayer films were studied. The results show that the photocurrent generation properties of the film strongly depend on the radius of the metal ions coordinated with the aza-15-crown-5 ring of the dye.

  一种新型两亲性发色团--N-[4-(2,3,6,7,8,9,11,12-八氢-5H-1,4,10,13,7-苯并四氧杂氮杂环十五烷-7-基)丁基]-4-2-[4-(N-甲基-N-十六烷基氨基)苯基]乙烯基}溴化喹啉(Crown D)、合成了含有 DÏâA苯乙烯基染料和氮杂-15-冠醚-5 基团的皇冠 D，并利用 LangmuirâBlodgett 技术成功地将其转移到了氧化铟锡（ITO）电极上。研究了不同金属阳离子子相对皇冠 D ÏâA 等温线的影响。研究了发色团枸橼酸单层膜的光电转换特性。结果表明，薄膜的光电流产生特性在很大程度上取决于与染料的氮杂-15-冠-5 环配位的金属离子的半径。
• Multifunctional photoelectrochemical logic gates based on a hemicyanine sensitized semiconductor electrode
  作者：Fuyou Li、Mei Shi、Chunhui Huang、Linpei Jin

  DOI：10.1039/b502692j

  日期：——

  A new amphiphilic hemicyanine dye, (E)-1,3,3-trimethyl-2-[2-(4-N-methyl-N-hexadecylaminophenyl)ethenyl]indolinium iodide (MHID) has been synthesized and successfully transferred onto a semiconducting transparent indium-tin oxide (ITO) electrode by Langmuir–Blodgett (LB) techniques. The photoelectric conversion properties of the dye MHID monolayer fabricated ITO electrode have been investigated in a three electrode photoelectrochemical cell. The observed photocurrent strongly depends on the applied electrode potential and the concentrations of the electron acceptors and donors. By using electron acceptors and (or) donors as input and photocurrent as output, respectively, we have fabricated this artificial photoelectrochemical system as multifunctional logic gates, corresponding to a series of logic operations (YES, OR, XOR and INHIBIT). Importantly, the gates of this photoelectrochemical system have been interconnected to demonstrate computation as a half-subtractor, with Eu3+ and hydroquinone (H2Q) as the two inputs and the cathodic photocurrent and the absolute value of the photocurrent as the two outputs, respectively.

  研究人员合成了一种新型两性半氰胺染料--(E)-1,3,3-三甲基-2-[2-(4-N-甲基-N-十六烷基氨基苯基)乙烯基]碘化吲哚鎓（MHID），并通过朗缪尔-布洛杰特（LB）技术将其成功转移到半导体透明氧化铟锡（ITO）电极上。在三电极光电化学电池中研究了染料 MHID 单层 ITO 电极的光电转换特性。观察到的光电流在很大程度上取决于施加的电极电位以及电子受体和供体的浓度。通过将电子受体和（或）供体分别作为输入和光电流作为输出，我们将这种人工光电化学系统制作成了多功能逻辑门，与一系列逻辑运算（YES、OR、XOR 和 INHIBIT）相对应。重要的是，这个光电化学系统的门被相互连接起来，以半分流器的形式进行计算，Eu3+和对苯二酚（H2Q）分别作为两个输入，阴极光电流和光电流的绝对值作为两个输出。
• Dipole reversal in Langmuir–Blodgett films of an optically nonlinear dye and its effect on the polarity for molecular rectification
  作者：Geoffrey J. Ashwell、Benjamin J. Robinson、Mukhtar A. Amiri、Danika Locatelli、Silvio Quici、Dominique Roberto

  DOI：10.1039/b506765k

  日期：——

  Langmuir–Blodgett (LB) films of isomeric donor–(π-bridge)–acceptor molecules with either a hydrophobically substituted acceptor [D–π–A–C16H33 (1)] or donor [A–π–D–C16H33 (2)] exhibit second-harmonic generation and asymmetric current–voltage characteristics: a reversed polarity for rectification arises from an inversion of the dipole orientations in the two types of monolayer.

  Langmuir-Blodgett（LB）薄膜中异构体供体（-桥）受体分子具有疏水取代的受体[D-C16H33（1）]或供体[A-C16H33（2）]，表现出二次谐波产生和非对称电流-电压特性：两种单层中的偶极子方向反转，产生反向极性整流。
• Novel Multifunctional Umbrella Molecule Material Combining Photoelectric Conversion and Second-Order Optical Nonlinearities in Langmuir−Blodgett Monolayers
  作者：Fu-You Li、Jie Zheng、Chun-Hui Huang、Lin-Pei Jin、Jin-You Zhuang、Jian-Quan Guo、Xin-Sheng Zhao、Ting-Ting Liu

  DOI：10.1021/jp993605u

  日期：2000.6.1

  A dipolar two-dimensional multifunctional (D-pi)(3)-A dye molecule, 3,4,6-tris(4-(N-methyl-N-hexaclecylamino)-styryl)pyrylium tetrafluoroborate (P-3) was synthesized. The dye molecule was successfully transferred onto an ITO electrode or quartz by the Langmuir-Blodgett (LB) technique. The second-harmonic generation (SHG) and photoelectric conversion (PEC) properties of the "molecular umbrella" monolayers were studied under 10 and 40 mN m(-1) surface pressure. The different tilt angle of the "molecular umbrella" results in the difference of SHG and PEC properties; For comparison, dipolar one-dimensional molecule 2,6-dimethyl-4-(4-(N-methyl-N-hexadecylamino)styryl)pyrylium tetrafluoroborate (P-1) was also investigated. The experimental results show that the SHG and PEC properties of the dipolar two-dimensional molecule (P-3) are better than those of the dipolar one-dimensional molecule (PI). For example, under favorable conditions (-100 mV, dissolved Oz, 2 mM MV2+, and 4 mM EU3+), the quantum yields for P-3 and P-1 monolayers (deposited under 40 mN m(-1)) are 1.21 and 0.42%, respectively.
• Photoelectric Conversion Properties of Nanocrystalline TiO₂ Electrodes Sensitized with Hemicyanine Derivatives
  作者：Zhong-Sheng Wang、Fu-You Li、Chun-Hui Huang、Lu Wang、Min Wei、Lin-Pei Jin、Nan-Qiang Li

  DOI：10.1021/jp001580p

  日期：2000.10.1

  Four hemicyanine derivatives, (E)-N-(3-sulfopropyl-4-[2-(4-dimethylaminophenyl)ethenyl]pyridinium (PS), (E)-N-(3-sulfopropyl-4-[2-(4-dimethylamiophenyl)ethenyl]quinolinium (QS), CE)-N-(3-sulfopropyl-4-[2-(4-N-methyl-N-hexadecylaminophenyl)ethenyl]pyridinium (LPS), and (E)-N-(3-sulfopropyl-4-[2-(4-N-methyl-N-hexadecylaminophenyl)ethenyl]quinolinium (LQS), have been synthesized and characterized with regard to their absorption and electrochemical properties. Photoelectrochemical experiments show that these hemicyanine dyes with D-pi -A systems can yield efficient charge separation under illumination of simulated solar light. Alkyl chain has a remarkable effect on dye adsorbance, incident photon-to-electron conversion efficiency, and overall energy conversion yield. The overall yield is approximately doubled when the methyl group replaces the: long alkyl chain. Action spectrum of QS displayed a broad feature with 33.8% of maximum monochromatic incident photon-to-electron conversion efficiency (IPCE), and a thin-layer sandwich-type solar cell based on nanocrystalline TiO2 film modified with QS produced about 2% of overall yield for the first time, a photovoltaic liquid-junction solar cell based on nanostructured TiO2 electrode sensitized by hemicyanine dyes is reported.