8-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde | 1160424-47-4

• 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: 8-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde
• CAS: 1160424-47-4
• 化学式: C₂₉H₄₉NO₃Si
• 分子量: 487.798
• InChiKey: IGESAYBDMDJRPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Donor modification of nonlinear optical chromophores: Synthesis, characterization, and fine-tuning of chromophores' mobility and steric hindrance to achieve ultra large electro-optic coefficients in guest–host electro-optic materials

  摘要：

  We synthesized three new donor-modified push-pull chromophores with the same divinylenethio-phenyl bridge and tricyanofuran acceptor, but with different modified donor moieties. Structure analysis and photophysical properties were carried out to compare the molecular mobility and steric hindrance effect of different donor-modified chromophores. Density functional theory calculations and thermal properties showed the different results of chromophores' microscopic nonlinearity and thermal stability. In electro-optic activities, the poling process demonstrated that guest-host electro-optic polymers containing the chromophores with different steric hindrance and molecular free mobility, required different optimal poling condition to achieve the large macroscopic electro-optic coefficients. After the exploration of the poling condition, it showed an ultra large electro-optic coefficient (266 pm/V) for electro-optic polymer WJ5-APC-2, which indicated the fine-tuning of steric hindrance and molecular free mobility of chromophore WJ5 in host polymer APC-2. Meanwhile, steric hindrance also improved the temporal stability of electro-optic coefficients for WJ5-APC-2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.12.023
• 作为产物：
  描述：

  6-氯-1-己醇 在 咪唑 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 8-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde
  参考文献：
  名称：

  合成新型非线性光学发色团以实现超高电光活性。

  摘要：

  通过H键诱导的Vilsmeier反应合成了新型的二烯共轭生色团WJ1，收率达36％。通过简单的客体-主体掺杂，在WJ1 / APC的极化薄膜中，负载密度为40 wt％，在1310 nm处实现了337 pm V（-1）的大电光效率和在75摄氏度下的出色的时间稳定性。 ％。

  DOI：

  10.1039/c2cc34747d

文献信息

• 具有D-π-A结构的有机二阶非线性光学发色 团及合成方法和用途
  申请人：中国科学院理化技术研究所

  公开号：CN104558004B

  公开（公告）日：2017-12-15

  本发明涉及有机二阶非线性光学材料领域，特别涉及以久洛尼定或其衍生物为电子给体，以噻吩环或环多烯结构为共轭电子桥，以三氰基二氢呋喃或三氟取代的三氰基二氢呋喃为电子受体的具有D‑π‑A结构的有机二阶非线性光学发色团及其合成方法和用途。本发明所使用的电子给体、共轭π电子桥和电子受体组合在一起后既能很好的提高分子内电子传输能力，又能增加分子间位阻。因此，该类结构能有效提高发色团分子的一阶分子超极化率（β），并能有效降低分子间相互作用力。将所述有机二阶非线性光学发色团与无定型聚碳酸酯掺杂可用于制备极化聚合物薄膜，该极化聚合物薄膜可作为光信号调制领域中的材料使用。所述有机二阶非线性光学发色团具有以下结构。
• Synthesis of novel nonlinear optical chromophores: achieving enhanced electro-optic activity and thermal stability by introducing rigid steric hindrance groups into the julolidine donor
  作者：Hua Zhang、Hongyan Xiao、Fenggang Liu、Fuyang Huo、Yanling He、Zhuo Chen、Xinhou Liu、Shuhui Bo、Ling Qiu、Zhen Zhen

  DOI：10.1039/c6tc05414e

  日期：——

  functional theory (DFT) was used to calculate the HOMO–LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. Besides, to determine the redox properties of these chromophores, cyclic voltammetry (CV) experiments were performed. All these four chromophores showed superb thermal stabilities with high thermal decomposition temperatures above 265 °C. Most importantly, the introduction

  基于由四个不同的刚性位阻基团包括苯，2,3,4,5,6-五氟苯，3,5-双（苄氧基）苯和3,5修饰的聚甲基吡啶供体，合成了一系列发色团z1-z4 -双（2,3,4,5,6-五氟苯甲酸酯）苯，分别具有相同的噻吩桥和强三氰基乙烯基二氢呋喃（TCF）受体，且收率高。密度泛函理论（DFT）用于计算HOMO-LUMO能隙和一阶超极化率（β）这些发色团。此外，为了确定这些生色团的氧化还原性质，进行了循环伏安法（CV）实验。所有这四个生色团均具有出色的热稳定性，并且在265°C以上的高温下具有较高的热分解温度。最重要的是，引入刚性位阻基团可以有效减少偶极-偶极相互作用，从而将其相对的β值转化为大量的高EO活性。通过在APC中以25 wt％的高负载量掺杂发色团z1-z4，在1310 nm处可分别获得高达99、104、97和89 pm V -1的EO系数（r 33）。归一化的r 33值增加到6.84×10 -18z4的每立方米（V分子）pm
• Structure–function relationship exploration for enhanced electro-optic activity in isophorone-based organic NLO chromophores
  作者：Fenggang Liu、Hua Zhang、Hongyan Xiao、Huajun Xu、Shuhui Bo、Ling Qiu、Zhen Zhen、Lijie Lai、Shujie Chen、Jiahai Wang

  DOI：10.1016/j.dyepig.2018.04.036

  日期：2018.10

  the macroscopic electro-optic efficiency. The chromophore FLD3 possesses better thermal stability than chromophore FLD1 without the isolation group on the bridge. Moreover, density functional theory calculations suggested that the hyperpolarizability (β) value of chromophore FLD3 is larger than that of chromophore FLD1. Polymers doped with chromophore FLD3 have been poled to afford ultrahigh electro-optic

  合成了四种基于异佛尔酮的生色团FLD1-FLD4，并基于朱螺啶基供体，并修饰了异佛尔酮衍生的桥和三氰基乙烯基二氢呋喃或苯基-三氟甲基-三氰呋喃受体。发色团FLD3被共价连接到π-共轭桥的2-（（叔丁基二甲基甲硅烷基）氧基）乙硫醇基团修饰，以确保其全反式构象并防止分子的紧密堆积，这有利于宏观电光效率。发色团FLD3具有比在桥上没有隔离基团的发色团FLD1更好的热稳定性。此外，密度泛函理论计算表明，发色团FLD3的超极化率（β）值大于发色团FLD1的超极化率。33）在1.31μm时为238 pm / V，比发色团FLD1高近60％，比类似发色团FLD2和FLD4高三倍。
• Tailoring the chemical structures and nonliear optical properties of julolidinyl-based chromophores by molecular engineering
  作者：Zhuo Chen、Airui Zhang、Hongyan Xiao、Fuyang Huo、Zhen Zhen、Xinhou Liu、Shuhui Bo

  DOI：10.1016/j.dyepig.2019.107876

  日期：2020.2

  5-dihydrofuran)) were synthesized and characterized. The microscopic nonlinear optical properties including solvent dependence of dipole moment (μ), hyperpolarizability (β), static polarizability (ɑ), and bond length alternation (BLA) of all chromophores were demonstrated by density functional theory (DFT) calculations. The macroscopic properties of EO effect were measured by simple reflection method, and the highest

  为了研究组分对非线性（NLO）光学性能的影响，一系列NLO发色团包含朱螺啶基作为电子供体，两种π共轭桥（二乙烯基异佛尔酮，二乙烯基噻吩），两种电子受体（TCF） （2-二氰基亚甲基-3-氰基-4,5,5-三甲基-2,5-二氢呋喃）和CF 3合成并表征了-Ph-TCF（2-二氰基亚甲基-3-氰基-4,5-二甲基-5-三氟甲基-2,5-二氢呋喃）。通过密度泛函理论（DFT）计算证明了所有生色团的微观非线性光学性质，包括偶极矩对溶剂的依赖性（μ），超极化率（β），静态极化率（ɑ）和键长交替（BLA）。通过简单反射法测量了EO的宏观特性，最高EO系数（r 33）为256 pm / V。还评估了溶剂溶变色行为和热稳定性以研究结构-性质关系。这项研究解释了微观结构对基于聚氯吡啶基的发色团的宏观性能的影响。
• Thermally Stable Nonlinear Optical Polymers Based on Polyimides Substituted with Chromophores Containing Julolidine Moiety
  作者：Hyun Kyung Ju、Jong Sun Lim、Changjin Lee、Dong Hoon Choi、Dong Wook Kim

  DOI：10.1080/15421400802329590

  日期：2008.9.30

  We designed and synthesized a NLO chromophore adopting the concept of shape modification as well as possessing high thermal stability. The chromophore was featured by a phenylene ring as a conjugation bridge, a bulky alkyl chain attached on the side of the conjugation bridge, and julolidine moiety as an electron donor. The NLO chromophore was attached to the polyimide as a side chain, resulting in thermally durable NLO polymers. On set decomposition temperature of the NLO chromophore was measured 330 degrees C in TGA analysis. The NLO polymer exhibited high glass transition temperature of 150 degrees C and was thermally stable up to 250 degrees C. The polymer was quite soluble in common solvents and produced an optical quality film by spin-coating. The electro-optic coefficient of the film was measured using 1.55 mu m laser source, giving as high as 30 pm/V at the poling condition of 150 degrees C and 1 MV/cm.