diethyl (2,5-bisbutoxy-4-bromobenzyl)phosphonate | 960081-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (2,5-bisbutoxy-4-bromobenzyl)phosphonate
• CAS: 960081-01-0
• 化学式: C₁₉H₃₂BrO₅P
• 分子量: 451.338
• InChiKey: DKMKETJSXNIYFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  26.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl (2,5-bisbutoxy-4-bromobenzyl)phosphonate 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4,4'-bis(2,5-dibutoxy-4-(2,5-dimethoxy-4-dibutylaminostyryl)styryl)-2,2'-bipyridine
  参考文献：
  名称：

  D-π-A-A-π-D Prototype 2,2′-Bipyridine Dyads Exhibiting Large Structure and Environment-Sensitive Fluorescence: Synthesis, Photophysics, and Computation

  摘要：

  A series of 4,4'-pi-conjugated-2,2'-bipyridine chromophores (MS 1-8) were synthesized, and their photo-physical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a pi-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-pi-A-A-pi-D dyad archetype in which the A-A is the central 2,2'-bipyridine acceptor core that is electronically attached with the donor termini through pi-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field.

  DOI：

  10.1021/jo202015m
• 作为产物：
  描述：

  1-bromo-2,5-bisbutoxy-4-(bromomethyl)benzene 、 亚磷酸三乙酯 反应 2.0h， 以100%的产率得到diethyl (2,5-bisbutoxy-4-bromobenzyl)phosphonate
  参考文献：
  名称：

  通过氢键手性酸在寡聚（对亚苯基亚乙烯基）装配体中进行螺旋诱导和扩增。

  摘要：

  DOI：

  10.1002/anie.200702730

文献信息

• Asymmetrically Substituted and π-Conjugated 2,2′-Bipyridine Derivatives: Synthesis, Spectroscopy, Computation, and Crystallography
  作者：Ramakrishna Bodapati、Monima Sarma、Arunkumar Kanakati、Samar K. Das

  DOI：10.1021/acs.joc.5b02345

  日期：2015.12.18

  A new series of monosubstituted styryl- and bistyryl-2,2′-bipyridine luminophores (compounds 16–23) have been synthesized via Horner–Wadsworth–Emmons reaction involving a monophosphonate and donor aromatic aldehydes. In the title chromophores, the amino donors are varied between acyclic and cyclic while the alkoxy donors are varied in terms of their number and position. The absorption maxima of these

  一系列新的单取代的苯乙烯基和双苯乙烯基-2,2'-联吡啶发光体（化合物16 – 23）是通过霍纳-沃兹沃思-埃蒙斯反应合成的，涉及单膦酸酯和给体芳族醛。在标题发色团中，氨基供体在无环和环状之间变化，而烷氧基供体的数目和位置不同。这些生色团的吸收最大值主要是由于不同供体和受体部分之间的分子内电荷转移（ICT）引起的。标题供体-受体分子在室温下的溶液中表现出强烈的荧光，并且发现其发射行为对溶剂极性高度敏感。所有的发色团的荧光光谱和量子产率被记录在四个不同的溶剂介质，以及发色团16，17，19，和21也表现出固态荧光。供体官能团的性质和位置的在标题的发色团（电子吸收特性的联吡啶基部分的共轭主链的影响16 - 23）已被证实，其还进一步由DFT和TD-DFT计算证实这两种在气相和溶液相中。化合物的晶体结构18已被描述为家庭（代表构件16 - 23）。
• Carbazole-based π-conjugated 2,2′-Bipyridines, a new class of organic chromophores: Photophysical, ultrafast nonlinear optical and computational studies
  作者：Ramakrishna Bodapati、Gaurav Ranjan Dey、Gunjan R. Ramteke、Katturi Naga Krishnakanth、S. Venugopal Rao、K.V.Jovan Jose、Samar K. Das

  DOI：10.1016/j.dyepig.2020.108932

  日期：2021.2

  chromophores with large two-photon absorption (2 PA) cross-sections are essential for myriad of applications, ranging from nonlinear microscopy to biomedical imaging. Here, we present the results from a comprehensive study of 2 PA cross-sections of a new series of carbazole mono substituted-π-conjugated-2,2′-bipyridine derivatives with D-π-A architecture, possessing carbazole as the donor moiety and

  具有大的双光子吸收（2 PA）截面的基于供体-受体（DA）架构的有机发色团的开发对于从非线性显微镜到生物医学成像的各种应用都是必不可少的。在这里，我们提出了对具有咔唑作为供体部分的具有D-π-A结构的一系列新的咔唑单取代-π-共轭-2,2'-联吡啶衍生物系列的2 PA截面的综合研究结果联吡啶核心为受体。此外，我们通过引入苯基和丁氧基取代的苯基连接基扩展了π-共轭。这些DA生色团的荧光性质对溶剂极性和电子给体功能的改变高度敏感。相关的计算研究支持我们的实验结果，例如，发射最大值的移动和分子的带隙。标题供体-受体（DA）生色团的三阶非线性光学（NLO）特性表明，使用〜50 fs（fs）激光脉冲在90℃下获得的2 PA截面值在6–39 GM范围内。波长为800 nm。此外，非线性折射率（n发现2）这些发色团为〜10 -14  cm 2 / W，由于系数是用kHz，fs脉冲提取纯电子非线性而获得的