2-butoxy-4-(diethylamino)benzaldehyde | 67676-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-butoxy-4-(diethylamino)benzaldehyde
• 英文别名: 4-(diethylamino)-2-butoxybenzaldehyde
• CAS: 67676-52-2
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: LGUAOXHOALIAEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-butoxy-4-(diethylamino)benzaldehyde 在 selenium(IV) oxide 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  基于苯胺供体部分不同基团的推拉式喹喔啉发色团复合聚合物材料的二次非线性光学响应

  摘要：

  开发了以喹喔啉核为共轭桥的原始推拉发色团掺杂的复合高分子材料。在苯胺供体部分和三氰基呋喃受体中具有各种取代基的发色团具有高热稳定性和第一超极化率预测值（高达 1000 × 10 -30 esu）的特点。电晕极化聚合物薄膜的非线性光学 (NLO) 系数d 33达到 75 pm V -1对于掺杂有N , N -dibutylamino-3-ethylbenzone 供体的发色团的材料，含量为 25 wt%，同时掺杂具有受体中额外庞大的环己基苯基导致最大d 3340 wt% 发色团含量的值为 97 pm V -1 ，纯发色团材料的值为 65 pm V -1。NLO 响应在室温和加热至 50 °C 100 小时内的时间和热稳定性被证明是高的：对于一些聚合物材料，d 33的值在室温下 24 个月内几乎保持不变并且至少为 94%加热后保留的反应。

  DOI：

  10.1039/d2nj05759j
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 生成 2-butoxy-4-(diethylamino)benzaldehyde
  参考文献：
  名称：

  Synthesis of novel colorants for DSSC to study effect of alkyl chain length alteration of auxiliary donor on light to current conversion efficiency

  摘要：

  Five (MA1-MA5) hemicyanine based sensitizer having N, N-diethyl aniline as a primary donor and hydroxy or alkoxy as an auxiliary donor have been synthesized to establish a correlation between amphiphilic nature of the sensitizer and charge recombination. A strong electron withdrawing 3-(carboxymethyl)-2-methylbenzo[d]thiazol-3-ium bromide has been explored as an acceptor. All the dyes were characterized by H-1-NMR, C-13-NMR and CHN analysis. The photophysical properties of these dyes were recorded in seven different solvents which do not show any significant impact on absorption and emission maxima while molar absorptivity coefficient decreases with increase in alkyl chain length. These dyes show very poor emission in all the solvents. Nano crystalline mesoporous TiO2 based dye-sensitized solar cells were fabricated using MA1 to MA5 sensitizers to evaluate their photovoltaic performance. MA5 having six carbon alkyl chain shows maximum efficiency of 4.97% while MA1 without any alkyl chain shows the lowest efficiency of 3.40%. As the length of alkyl chain increase efficiency increase due to increment in short circuit current (J(sc)) and retardation in the recombination process. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) were explored to obtain vertical excitation, HOMO-LUMO energy and electron density distribution.

  DOI：

  10.1016/j.jphotochem.2019.03.043

文献信息

• Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor
  作者：Guillaume Noirbent、Corentin Pigot、Thanh-Tuân Bui、Sébastien Péralta、Malek Nechab、Didier Gigmes、Frédéric Dumur

  DOI：10.1016/j.dyepig.2020.108807

  日期：2021.1

  A series of chromophores was designed and synthesized using 2-(3-cyano-4,5,5-trimethylfuran-2 (5H) -ylidene) malononitrile (TCF) as the electron acceptor and differing from each other by the use of thirteen different electron donors. The different dyes were characterized for their optical and electrochemical properties and theoretical calculations were also carried out to support the experimental results

  以2-（3-氰基-4,5,5-三甲基呋喃-2（5 H）-亚烷基）丙二腈（TCF）为电子受体，设计并合成了一系列生色团，其中十三种彼此不同不同的电子给体 对不同染料的光学和电化学性质进行了表征，并进行了理论计算以支持实验结果。通过改变十三种染料中的电子给体，可以合成吸收在430 nm和700 nm之间的发色团。在23种不同极性的溶剂中分析了不同染料的溶剂变色现象，并基于Kamlet-Taft参数（π*）或加泰罗尼亚参数（SdP和SPP），使用半经验溶剂极性标度对所有生色团确定了正溶剂化变色现象。
• Dyes with tunable absorption properties from the visible to the near infrared range: 2,4,5,7-Tetranitrofluorene (TNF) as a unique electron acceptor
  作者：Guillaume Noirbent、Corentin Pigot、Thanh-Tuân Bui、Sébastien Péralta、Malek Nechab、Didier Gigmes、Frédéric Dumur

  DOI：10.1016/j.dyepig.2021.109250

  日期：2021.5

  5,7-tetranitrofluorene (TNF) as the electron acceptor have been designed and prepared in a one-step synthesis. By modifying the electron donor, optical properties of the dyes could be efficiently tuned and an absorption ranging between 450 nm and 700 nm could be determined by UV-visible absorption spectroscopy. To get a deeper insight into the optical properties, solvatochromism of the fourteen dyes

  以一步合成法设计并制备了基于2,4,5,7-四硝基芴（TNF）作为电子受体的十四种染料。通过修饰电子给体，可以有效地调节染料的光学性质，并且可以通过紫外-可见吸收光谱法确定450nm至700nm之间的吸收范围。为了更深入地了解光学性能，还检查了这十四种染料的溶剂变色现象。对于所有染料，使用不同的溶剂极性标度（例如，Kamlet-Taft和加泰罗尼亚经验标度）确定了正溶剂溶变色。最后，还检查了电化学性能，可以建立电化学带隙和光学带隙的比较。还进行了理论计算以表征不同的染料。
• A new family of bis-DCM based dopants for red OLEDs
  作者：Byung-Jun Jung、Jeong-Ik Lee、Hye Yong Chu、Lee-Mi Do、Jaemin Lee、Hong-Ku Shim

  DOI：10.1039/b419408j

  日期：——

  We have synthesized a series of novel bis-DCM derivatives as candidate red dopants for use in organic light-emitting devices (OLEDs), by introducing various donor-substituted aryl rings. Compared to DCJTB (621 nm), the novel dopants (637–677 nm) showed more red-shifted emission in 1,2-dichloroethane. Using bis-DCMNEtOBu (7) as a dopant, we fabricated OLEDs with the configuration of ITO/4,4′,4″-tris(3-methylphenylamino)triphenylamine (m-MTDATA) (20 nm)/N,N′-bis(1-naphthyl)-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB) (40 nm)/tris(8-quinolinolato)aluminium (Alq3) : red dopant (35 nm, x wt%)/Alq3 (35 nm) LiF/Al. The device with a doping concentration of 1.25 wt% showed pure red emission at λmax = 654 nm (chromaticity coordinate: x = 0.67, y = 0.33) and a maximum brightness of 2500 cd m−2. The chromaticity coordinates were almost independent of current density. Moreover, highly efficient red emission (x = 0.63, y = 0.36) was obtained in the 0.74 wt% doped device. The maximum external quantum efficiency was 4.46% at 7 V, the current efficiency was 3.43 cd A−1, and the power efficiency was 1.64 lm W−1. The highest brightness of 8300 cd m−2 was obtained at 19.6 V.

  我们通过引入各种供体取代的芳基环，合成了一系列新型双二氯甲烷衍生物，作为有机发光器件（OLED）的候选红色掺杂剂。与 DCJTB（621 纳米）相比，新型掺杂剂（637-677 纳米）在 1,2 二氯乙烷中显示出更多的红移发射。使用双-DCMNEtOBu (7) 作为掺杂剂，我们制备了配置为 ITO/4,4′,4″-三（3-甲基苯基氨基）三苯胺 (m-MTDATA) (20 nm)/N、N′-双(1-萘基)-二苯基-1,1′-联苯-4,4′-二胺 (NPB) (40 纳米)/三(8-喹啉醇)铝 (Alq3) ：红色掺杂剂（35 nm，x wt%）/Alq3 (35 nm) LiF/Al。掺杂浓度为 1.25 wt% 的器件在 λmax = 654 nm（色度坐标：x = 0.67，y = 0.33）处显示出纯红色发射，最大亮度为 2500 cd m-2。色度坐标几乎与电流密度无关。此外，在掺杂 0.74 wt% 的器件中还获得了高效的红色发射（x = 0.63，y = 0.36）。7 V 时的最大外部量子效率为 4.46%，电流效率为 3.43 cd A-1，功率效率为 1.64 lm W-1。在 19.6 V 时，亮度最高，达到 8300 cd m-2。
• Cooperative enhancement of optical nonlinearities in a porphyrin derivative bearing a pyrimidine chromophore at the periphery
  作者：Aijian Wang、Lingliang Long、Suci Meng、Xiufen Li、Wei Zhao、Yinglin Song、Marie P. Cifuentes、Mark G. Humphrey、Chi Zhang

  DOI：10.1039/c3ob40323h

  日期：——

  A novel porphyrin derivative bearing one D–π–A–π–D pyrimidine chromophore at the periphery was designed, prepared, and studied using the Z-scan technique, the results showing that this compound exhibits enhanced nonlinear optical (NLO) absorption, refraction and optical limiting responses. The significant NLO properties can be ascribed to an effective combination of distinct nonlinear mechanisms.

  研究人员设计、制备了一种新型卟啉衍生物，其外围含有一个 D-π-A-π-D 嘧啶发色团，并利用 Z 扫描技术对其进行了研究，结果表明该化合物具有增强的非线性光学（NLO）吸收、折射和光学限制响应。显著的 NLO 特性可归因于不同非线性机制的有效结合。
• Proton-induced fluorescent switching of a new 2D-π-A type vinylcyanoacetate-pyran dye
  作者：Sheng Wang、Sung-Hoon Kim

  DOI：10.1016/j.saa.2008.10.035

  日期：2009.4

  A new 2D-pi-A type vinylcyanoacetate-pyran dye, ethyl 2-(2,6-bis(2-butoxy-4-(diethylamino)styryl)-4H-pyran-4-ylidene)-2-cyanoacetate (BDPC) was prepared by condensation reaction. The chemical structures of all the intermediates and the BDPC dye are characterized by (1)H NMR, MS. It showed interestingly solvatochromic and solvatofluorchromic properties in various solvents. Its LUMO and HOMO values were

  一种新型2D-pi-A型乙烯基氰乙酸酯-吡喃染料，2-（2,6-双（2-丁氧基-4-（二乙基氨基）苯乙烯基）-4H-吡喃-4-亚烷基）-2-氰基乙酸乙酯（BDPC）通过缩合反应制备。所有中间体和BDPC染料的化学结构均通过（1）H NMR，MS表征。它有趣地显示了在各种溶剂中的溶剂变色和溶剂化荧光变色性质。通过理论计算获得其LUMO和HOMO值。可以通过控制分子内电荷转移（ICT）通过胺部分的质子化/去质子化来可逆地选择BDPC染料的荧光强度，从而导致荧光分子开关具有两个不同的“开”和“关”状态。