4-(N,N-dihexadecylamino)benzaldehyde | 131814-01-2

• 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,N-dihexadecylamino)benzaldehyde
• 英文别名: 4-(Dihexadecylamino)benzaldehyde；4-(dihexadecylamino)benzaldehyde
• CAS: 131814-01-2
• 化学式: C₃₉H₇₁NO
• 分子量: 569.999
• InChiKey: LTAAWGZZJHQGPY-UHFFFAOYSA-N

物化性质

• 沸点：
  650.8±38.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  41
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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,N-dihexadecylamino)benzaldehyde 在 咪唑 、 四氯化碳 、 氢氧化钾 、 三苯基膦 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丁酮 为溶剂， 反应 90.0h， 生成 4-N,N-dihexadecylamino-4'-{2-[2-(2-iodoethoxy)ethoxy]ethoxy}chalcone
  参考文献：
  名称：

  Micelles of Lipid−Oligonucleotide Conjugates:  Implications for Membrane Anchoring and Base Pairing

  摘要：

  This report examines the organization properties of new fluorescent DNA-lipids, either alone in water or in interaction with 1-otyl-beta-D-glucopyranoside micelles or egg phosphatidylcholine vesicles. We first describe the design and the syntheses of the conjugates. Then, we use UV-Vis absorption, steady-state fluorescence emission, electron microscopy, and fluorescence correlation spectroscopy after two-photon excitation to show that these DNA-lipids form spherical micelles in aqueous solution and incorporate much better in micelles than in vesicles. We also investigate the significance of the lipophilic chains of these DNA-lipids on the melting behavior of the double-stranded hybrids: in water melting curves are broadened whereas in amphiphilic assemblies duplexes melt as the unconjugated controls. This work is expected to be useful for improving the rational design of antisense medicines.

  DOI：

  10.1021/jp031188m
• 作为产物：
  描述：

  2-(4-Dihexadecylamino-benzylidene)-dihydro-pyrimidine-4,5,6-trione 在 2,4,6-三氨基嘧啶 、 水 作用下， 反应 0.25h， 生成 4-(N,N-dihexadecylamino)benzaldehyde
  参考文献：
  名称：

  Bohanon, Thomas M.; Denzinger, Steffen; Fink, Ralf, Angewandte Chemie, 1995, vol. 107, # 1, p. 102 - 104

  摘要：

  DOI：

文献信息

• Effect of MCl2 (M=Hg, Zn, Cu) subphase on photoinduced electron transfer in a pyrazinium styryl dye Langmuir–Blodgett film
  作者：Jie Zheng、Fuyou Li、Xiaofen Yu、Chun-Hui Huang、Nianzhu Wu

  DOI：10.1039/b002087g

  日期：——

  An amphiphilic heteroaromatic styryl dye, 2-(4-dihexadecylaminostyryl)-1,5-dimethylpyrazinium iodide (I) was synthesized. Its Langmuir–Blodgett films fabricated from different subphases, namely pure water (Ia), 10−5 M CuCl2 (Ib), 10−5 M ZnCl2 (Ic) and 10−5 M HgCl2 (Id), were characterized by UV-Vis spectra and XPS measurements. The photoelectrochemistry of these film-modified conducting transparent indium–tin oxide (ITO) electrodes was investigated on a traditional three-electrode cell. The experimental data indicated that the films fabricated from different subphases have distinctive photoelectric responses. Under ambient conditions (0.5 M KCl), the quantum yields of photoelectric conversion were 0.03, 0.05, 0.06, and 0.1% for films Ia, Ib, Ic and Id, respectively. The effects of factors such as bias voltage, methylviologen (MV2+), and hydroquinone (H2Q) on the photocurrent generation were also investigated. Based on the experimental data, a possible mechanism of photoinduced electron transfer in this system is proposed.

  合成了一种两性杂芳香族苯乙烯基染料--2-（4-十六烷基氨基苯乙烯基）-1,5-二甲基吡嗪鎓碘化物（I）。通过紫外-可见光谱和 XPS 测量，对从不同子相（即纯水 (Ia)、10â5 M CuCl2 (Ib)、10â5 M ZnCl2 (Ic) 和 10â5 M HgCl2 (Id)）制备的 LangmuirâBlodgett 薄膜进行了表征。在传统的三电极电池上研究了这些薄膜改性导电透明氧化铟锡（ITO）电极的光电化学性质。实验数据表明，由不同子相制得的薄膜具有不同的光电响应。在环境条件（0.5 M KCl）下，薄膜 Ia、Ib、Ic 和 Id 的光电转换量子产率分别为 0.03、0.05、0.06 和 0.1%。此外，还研究了偏置电压、甲基viologen（MV2+）和对苯二酚（H2Q）等因素对光电流产生的影响。根据实验数据，提出了该系统中光诱导电子转移的可能机制。
• The investigation of second harmonic generation from novel molecules [(E)-N-alkyl-4-{2-[4-(dialkylamino)phenyl]ethenyl}pyridazinium iodide]
  作者：T-r. Cheng、C-h. Huang、L-b. Gan、C-p. Luo、A.-c. Yu、X-s. Zhao

  DOI：10.1039/a707724f

  日期：——

  (E)-N-Methyl-4-2-[4-(dihexadecylamino)phenyl]ethenyl}pyridazinium iodide (MHPd), (E)-N-octadecyl-4-2-[4-(dimethylamino)phenyl]ethenyl}pyridazinium iodide (OMPd), (E)-N-octadecyl-4-2-[4-(diethylamino)phenyl]ethenyl}pyridazinium iodide (OEPd), (E)-N-octadecyl-4-2-[4-(dibutylamino)phenyl]ethenyl}pyridazinium iodide (OBPd) have been designed and synthesized. Their Langmuir–Blodgett film forming properties and second harmonic generation were studied. According to the results observed, MHPd is the best among the four congeners. By comparing the NLO properties of OMPd with those of a known compound, OMPy [(E)-N-octadecyl-4-2-[4-(dimethylamino)phenyl]ethenyl}pyridinium iodide], the impairing effect of the second nitrogen in the six-membered pyridazine ring was examined experimentally and theoretically.

  (E)-N-甲基-4-2-[4-(二十六烷基氨基)苯基]乙烯基}碘化哒嗪鎓 (MHPd), (E)-N-十八烷基-4-2-[4-(二甲基氨基)苯基]乙烯基}碘化哒嗪 (OMPd)、(E)-N-十八烷基-4-2-[4-(二乙氨基)苯基]乙烯基}碘化哒嗪 (OEPd)、(E)-N-十八烷基-4-2-设计并合成了[4-(二丁基氨基)苯基]乙烯基}碘化哒嗪鎓(OBPd)。研究了它们的 Langmuir-Blodgett 成膜特性和二次谐波的产生。根据观察结果，MHPd是四种同类物中最好的。通过将OMPd的NLO性质与已知化合物OMPy [(E)-N-十八烷基-4-2-[4-(二甲基氨基)苯基]乙烯基}碘化吡啶]进行比较，发现第二个氮的削弱作用对六元哒嗪环的结构进行了实验和理论研究。
• Effect of heteroatoms on photocurrent generation from a series of styryl dye Langmuir–Blodgett films
  作者：Jie Zheng、Chun-Hui Huang、Tian-Xin Wei、Yan-Yi Huang、Liang-Bin Gan

  DOI：10.1039/a907576c

  日期：——

  A series of amphiphilic styryl dyes, 2-[4-bis(hexadecyl)aminostyryl]benzothiazole methiodide (BTM), 2-[4-bis(hexadecyl)aminostyryl]benzoxazole methiodide (BOM), and 2-[4-bis(hexadecyl)aminostyryl]benzimidazole methiodide (BIM), were synthesized and successfully transferred onto the conducting transparent indium–tin oxide (ITO) electrode as H-aggregates by using a Langmuir–Blodgett (LB) technique. The photoelectrochemistry of the dye monolayers was investigated in a traditional three-electrode cell. The coincidence of their action spectra with the absorption spectra on the ITO electrodes indicated that the aggregates of the dyes on the ITO electrodes were responsible for the generation of the cathodic photocurrents. Some factors such as applied bias voltage, electron donors and acceptors on the photocurrent generation have also been investigated. Under favorable conditions (−200 mV, 1 mg ml−1 methylviologen diiodide (MV2+)), the photoelectric conversion quantum yield can reach 4.2%, 0.96%, and 1.19% for BTM, BOM and BIM respectively. Semiempirical calculations indicated that charge-separated states of the dyes upon illumination are a key requirement for the photocurrent generation. A common mechanism of photocurrent generation in this system was proposed based on the experiments. Experimental results indicated that heteroatoms in the acceptor parts of the dyes have a great effect on the photocurrent generation.

  一系列两亲性苯乙烯基染料，2-[4-双（十六烷基）氨基苯乙烯基]苯并噻唑甲硫醚（BTM）、2-[4-双（十六烷基）氨基苯乙烯基]苯并恶唑甲硫醚（BOM）和2-[4-双（十六烷基）合成了）氨基苯乙烯基]苯并咪唑甲碘化物（BIM），并使用 Langmuir-Blodgett (LB) 技术成功地将 H 聚集体转移到导电透明氧化铟锡 (ITO) 电极上。在传统的三电极电池中研究了染料单层的光电化学。它们的作用光谱与 ITO 电极上的吸收光谱的一致性表明 ITO 电极上染料的聚集体负责阴极光电流的产生。还研究了一些因素，例如施加的偏压、电子供体和受体对光电流产生的影响。在有利条件下（≤200 mV、1 mg·ml≤1甲基紫罗碱二碘化物（MV2+）），BTM、BOM和BIM的光电转换量子产率分别可达4.2%、0.96%和1.19%。半经验计算表明，染料在光照下的电荷分离状态是光电流产生的关键要求。基于实验提出了该系统中光电流产生的常见机制。实验结果表明，染料受体部分的杂原子对光电流的产生有很大影响。
• An investigation on the two-photon absorption activity of various terpyridines and related homoleptic and heteroleptic cationic Zn(ii) complexes
  作者：Stefania Righetto、Sergio Rondena、Danika Locatelli、Dominique Roberto、Francesca Tessore、Renato Ugo、Silvio Quici、Silvia Roma、Dmitry Korystov、Vojislav I. Srdanov

  DOI：10.1039/b515129e

  日期：——

  The two-photon absorption (TPA) properties of various terpyridines of the kind [4′-(C6H4-p-X)-2,2′∶6′,2″-terpyridine] and related homoleptic and heteroleptic bis(terpyridine) cationic zinc(II) complexes were investigated by the TPA induced photoluminescence (TPA-PL) method in a femtosecond regime. It appeared that terpyridines bearing an X donor group are characterized by TPA cross sections among the largest ever reported for a molecule with a dipole symmetry whereas coordination to a Zn(II) center leads to a decrease of the TPA response.

  在飞秒范围内，通过TPA诱导光致发光（TPA-PL）方法研究了各种[4′-(C6H4-p-X)-2,2′∶6′,2″-三联吡啶]类三联吡啶以及相关的同价和异价双（三联吡啶）阳离子锌（II）复合物的双光子吸收（TPA）特性。 结果表明，带有X供体基团的三联吡啶具有迄今为止报道的最大偶极对称分子TPA截面，而与Zn（II）中心的配位则导致TPA响应降低。
• Highly efficient photoinduced electron transfer on a benzothiazolium styryl dye Langmuir–Blodgett monolayer modified-ITO electrode
  作者：Jie Zheng、Deng-guo Wu、Jin Zhai、Chun-hui Huang、Wei-wei Pei、Xi-cun Gao

  DOI：10.1039/a900527g

  日期：——

  An amphiphilic benzothiazolium styryl dye 2-(4-dihexadecylaminostyryl)benzothiazole methiodide (DBM) was synthesized and deposited on a conducting transparent indium–tin oxide (ITO) electrode in H-aggregates by using the Langmuir–Blodgett (LB) technique. Its photoelectrochemistry was investigated in a traditional three-electrode cell. Coincidence of its action spectrum and the absorption spectrum on the ITO indicated that DBM was responsible for the generation of the photocurrent. Under favorable conditions, its monolayer quantum yield can reach as high as 4.2%. A mechanism of photoinduced electron transfer in this system was proposed based on the experiments and theoretical calculations.

  通过朗缪尔-布洛杰特（LangmuirâBlodgett，LB）技术合成了一种两亲性苯并噻唑苯乙烯染料 2-（4-二十六烷基氨基苯乙烯基）苯并噻唑碘甲烷（DBM），并以 H-聚集体的形式沉积在导电的透明氧化铟锡（ITO）电极上。在传统的三电极电池中研究了它的光电化学性质。其作用光谱与 ITO 上的吸收光谱相吻合，表明 DBM 是产生光电流的原因。在有利条件下，其单层量子产率可高达 4.2%。根据实验和理论计算，提出了该系统中光诱导电子转移的机理。