1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde | 367909-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde
• 英文别名: 6-formyl-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline；1,2,2,4-tetramethyl-3,4-dihydroquinoline-6-carbaldehyde
• CAS: 367909-69-1
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: YFSBNVZQFZCCTP-UHFFFAOYSA-N

物化性质

• 沸点：
  318.4±42.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(噻吩甲基)膦酸二乙酯 、 1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到1,2,2,4-Tetramethyl-6-(2-thiophen-2-ylethenyl)-3,4-dihydroquinoline
  参考文献：
  名称：

  噻吩-π-共轭的供体-受体系统中的光诱导分子内电荷转移和S2荧光：实验和TDDFT研究。

  摘要：

  实验和理论方法用于研究新合成的噻吩-π-共轭的供体-受体化合物，发现它们在具有较大斯托克斯位移和强溶剂致变色性的极性溶剂中表现出有效的分子内电荷转移发射。为了深入了解这些化合物的溶剂变色行为，在Lippert-Mataga模型的基础上研究了光谱对溶剂极性的依赖性。我们发现这些供体-受体系统中的分子内电荷转移显着取决于噻吩基2-位的吸电子取代基。这些化合物在甲醇中的吸收和发射光谱与三氟乙酸浓度的相关性被用来确认分子内电荷转移发射。而且，计算得出的吸收和发射能量与实验值一致，表明荧光可以从不同的几何构型发出。此外，还观察到了其中一些化合物的新型S（2）荧光现象。荧光激发光谱用于确认S（2）荧光。我们证明，S（2）荧光可以通过这些分子的S（2）和S（1）状态之间的计算能隙来解释。此外，理论上预测了具有二乙基氰基甲基膦酸酯取代基的噻吩-π-共轭化合物的非线性光学行为。还观察到其中一些化合物的新型S

  DOI：

  10.1002/chem.200701868
• 作为产物：
  描述：

  苯胺 在 氢气 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 环己烷 、 苯 为溶剂， 55.0~120.0 ℃ 、1.0 MPa 条件下， 反应 30.0h， 生成 1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde
  参考文献：
  名称：

  有机染料对高效染料敏化太阳能电池的共敏化

  摘要：

  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

  DOI：

  10.1002/cssc.201200655

文献信息

• Dye-Sensitized Solar Cells Based on a Donor-Acceptor System with a Pyridine Cation as an Electron-Withdrawing Anchoring Group
  作者：Ming Cheng、Xichuan Yang、Jiajia Li、Cheng Chen、Jianghua Zhao、Yu Wang、Licheng Sun

  DOI：10.1002/chem.201200826

  日期：2012.12.7

  New hemicyanine dyes (CM101, CM102, CM103, and CM104) in which tetrahydroquinoline derivatives are used as electron donors and N‐(carboxymethyl)‐pyridinium is used as an electron acceptor and anchoring group were designed and synthesized for dye‐sensitized solar cells (DSSCs). Compared with corresponding dyes that have cyanoacetic acid as the acceptor, N‐(carboxymethyl)‐pyridinium has a stronger electron‐withdrawing

  新的半花菁染料（CM101，CM102，CM103和CM104）将四氢喹啉衍生物用作电子供体，将N-（羧甲基）-吡啶用作电子受体，并设计并合成了用于染料敏化太阳能电池的锚定基团（ DSSC）。与相应的以氰基乙酸为受体的染料相比，N-（羧甲基）-吡啶具有更强的吸电子能力，这会使染料的最大吸收量发生红移。基于染料CM101 – CM104的DSSC的光伏性能在很大程度上取决于染料的分子结构。正己基链和甲氧基。在AM 1.5辐射（100 mW cm -2）下，被染料CM104敏化的器件实现了7.0％的最佳转换效率（J sc = 13.4 mA cm -2，V oc = 704 mV，FF = 74.8％）。相反，通过参考染料CMR104用相同的供体但氰基乙酸作为受体敏化的装置给出了3.4％的效率（J sc = 6.2 mA cm -2，V oc = 730 mV，FF = 74.8％）。在相同条
• Highly efficient organic dyes containing a benzopyran ring as a π–bridge for DSSCs
  作者：Cheng Chen、Xichuan Yang、Ming Cheng、Fuguo Zhang、Jianghua Zhao、Licheng Sun

  DOI：10.1039/c3ra41583j

  日期：——

  A series of novel organic dyes containing a benzopyran ring as a π–bridge have been designed and applied in dye-sensitized solar cells (DSSCs). This series of dyes show the excellent DSSCs' performance, due to their efficient light-to-photocurrent conversion in the region from 380 nm to 600 nm, with the highest IPCE values exceeding 90%. Through modification of the donor units, an efficiency as high as 7.5% has been achieved under standard light illumination (AM 1.5G, 100 mW cm−2) by the dye CC103.

  我们设计了一系列含有苯并吡喃环作为Ïâ桥的新型有机染料，并将其应用于染料敏化太阳能电池（DSSC）。这一系列染料在 380 纳米到 600 纳米的区域内具有高效的光-光电流转换能力，最高 IPCE 值超过 90%，因而显示出卓越的 DSSC 性能。通过修饰供体单元，染料 CC103 在标准光照（AM 1.5G，100 mW cmâ2）下的效率高达 7.5%。
• Development of excellent long-wavelength BODIPY laser dyes with a strategy that combines extending π-conjugation and tuning ICT effect
  作者：Dakui Zhang、Virginia Martín、Inmaculada García-Moreno、Angel Costela、M. Eugenia Pérez-Ojeda、Yi Xiao

  DOI：10.1039/c1cp21038f

  日期：——

  By comparison and combination of two strategies, extending π-conjugation and tuning Intramolecular Charge Transfer (ICT) effect, new long-wavelength BODIPY dyes have been efficiently synthesized. The new chromophores exhibit good optical properties: high fluorescence quantum yields, exceptionally large molar extinction coefficients, narrow red-emission bands, and relatively large Stokes shifts etc., in polar or apolar solvents. Besides, the new dyes, under transversal pumping at 532 nm, exhibit highly efficient and stable laser emission tunable from the green to NIR spectral region (570–725 nm). Moreover, one of these new BODIPY derivatives shows cell membrane permeability and bright intracellular red fluorescence. These advantageous characteristics assure the potential of these dyes for biophotonic applications.

  通过比较和结合两种策略，即扩展Ï-共轭和调整分子内电荷转移（ICT）效应，高效合成了新型长波长 BODIPY 染料。新的发色团在极性或非极性溶剂中表现出良好的光学特性：高荧光量子产率、特别大的摩尔消光系数、窄的红色发射带以及相对较大的斯托克斯位移等。此外，这些新型染料在 532 纳米横向泵浦条件下，可在绿色到近红外光谱区（570-725 纳米）之间实现高效稳定的激光发射。此外，其中一种新型 BODIPY 衍生物还具有细胞膜渗透性和明亮的细胞内红色荧光。这些优势特性确保了这些染料在生物光子应用方面的潜力。
• Engineering of highly efficient tetrahydroquinoline sensitizers for dye-sensitized solar cells
  作者：Yan Hao、Xichuan Yang、Jiayan Cong、Anders Hagfeldt、Licheng Sun

  DOI：10.1016/j.tet.2011.11.004

  日期：2012.1

  Four novel tetrahydroquinoline dyes by inserting isophorone and/or thiophene moieties as pi bridge between the electron donating unit of substituted tetrahydroquinoline and the electron withdrawing unit of cyano carboxylic acid have been synthesized and successfully applied to dye-sensitized solar cells. Among them, DSCs sensitized by HYTIC, which shows the simplest molecular structure, exhibit improved efficiency of 7.0%. This by now is the highest efficiency for the reported tetrahydroquinoline sensitizers and comparable to the performance of N719-sensitized solar cells under the conditions employed here. (C) 2011 Elsevier Ltd. All rights reserved.
• Photoinduced intramolecular charge-transfer state in thiophene-π-conjugated donor–acceptor molecules
  作者：Ruikui Chen、Guangjiu Zhao、Xichuan Yang、Xiao Jiang、Jifeng Liu、Haining Tian、Yan Gao、Xien Liu、Keli Han、Mengtao Sun、Licheng Sun

  DOI：10.1016/j.molstruc.2007.05.045

  日期：2008.3

  Novel thiophene-pi-conjugated donor-acceptor molecules, 5-[2-(1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)-vinyl]-thiophene2-carbaldehyde (QTC) and (1-cyano-2-5-[2-(1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)-vinyl]-thiophen-2-yl}-vinyl)-phosphonic acid diethyl ester (QTCP), were designed and synthesized. Combined experimental and theoretical methods were performed to investigate the photoinduced intramolecular charge-transfer (ICT) processes of these compounds. Steady-state absorption and fluorescence measurements in different solvents indicate the photoinduced ICT characters of QTC and QTCP. Solvent dependency of the large Stokes shifts and high dipole moment of the excited state also support the charge-transfer character of the excited state. Theoretical calculations based on time-dependent density functional theory (TDDFT) method were performed to investigate ICT states of these compounds. The results reveal that the excited states have adopted a distortion of the C=C double bond between the donor moiety and the thiophene-pi-bridge. (c) 2007 Elsevier B.V. All rights reserved.