8-(diethylamino)-2,2-difluoro-4-methyl-5-oxo-2,5-dihydro-[1,3,2]dioxaborinino [5,4-c]chromen-3-ium-2-uide | 1097257-23-2

• 英文名称: 8-(diethylamino)-2,2-difluoro-4-methyl-5-oxo-2,5-dihydro-[1,3,2]dioxaborinino [5,4-c]chromen-3-ium-2-uide
• 英文别名: 8-(diethylamino)-2,2-difluoro-4-methyl-5-oxo-(5H)-chromeno[4,3-d]-1,3,2-(2H)-dioxaborine；2,2-difluoro-4-metyl-5-oxo-(5H)-8-(diethylamino)-chromeno[4,3-d]-1,3,2-(2H)-dioxaborine
• CAS: 1097257-23-2
• 化学式: C₁₅H₁₆BF₂NO₄
• 分子量: 323.104
• InChiKey: AURIKHGZWAHCRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  8-(diethylamino)-2,2-difluoro-4-methyl-5-oxo-2,5-dihydro-[1,3,2]dioxaborinino [5,4-c]chromen-3-ium-2-uide 、 3-(3-formyl-9H-carbazol-9-yl)propionic acid 在 哌啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以21%的产率得到
  参考文献：
  名称：

  Viscosity sensitive fluorescent coumarin-carbazole chalcones and their BF2 complexes containing carboxylic acid – Synthesis and solvatochromism

  摘要：

  Red emitting coumarin-carbazole chalcones of the D-pi -A and D-pi-A-pi-D type were synthesized with the coumarin core as acceptor and carbazole with anchoring carboxylic group at the end of N-alkyl chain as donor. The introduction of extra donor on the coumarin core led to bathochromic shift. Further, the BF2 complexation of the synthesized chalcones led to emission in red region due to efficient increase in the electron attracting capacity of coumarin acceptor. A strong emission solvatochromism than absorption was observed for the studied dyes which is well understood with the help of the multi-linear regression analysis. The frontier molecular orbital analysis of the dyes suggest strong intramolecular charge transfer characteristics. Viscosity induced emission enhancement was observed for all dyes in polar-protic (ethanol: PEG 400) solvent mixtures. As the dyes 6 and 8 emit at 612 nm and 647 nm in polar solvents these can be used as red emitting fluorescent molecular rotors. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2018.05.074
• 作为产物：
  描述：

  4-羟基-7-二乙氨基香豆素 在 吡啶 、 乙酸酐 作用下， 以 乙腈 为溶剂， 反应 14.67h， 生成 8-(diethylamino)-2,2-difluoro-4-methyl-5-oxo-2,5-dihydro-[1,3,2]dioxaborinino [5,4-c]chromen-3-ium-2-uide
  参考文献：
  名称：

  三苯胺衍生的香豆素查尔酮及其发射红色的OBO二氟化物配合物：合成，光物理和NLO性能研究

  摘要：

  合成并表征了辅助甲氧基辅助的三苯胺供体衍生的香豆素查尔酮及其具有支化供体-pi-受体体系的OBO配合物。在不同极性的溶剂中，对其光物理性质进行了广泛的研究。它们显示出很强的发射溶剂致变色现象，并且量子产率高达0.87。高炉2香豆素查耳酮的络合与未络合的查耳酮相比，量子效率提高了约1.4倍。前沿分子轨道分析和广义Mulliken Hush分析表明，这些生色团具有很强的分子内电荷转移特性。这些发色团的一级，二级和三级极化率通过溶剂变色法进行评估，并通过使用CAM-B3LYP / 6-31g（d）方法的密度泛函理论计算得到支持。通过Z扫描分析获得的这些生色团的三阶非线性光学磁化率显示的虚部值非常小。用芳基胺基团取代N-乙基供体可为支链推挽系统提供增强的热稳定性和非线性光学响应。

  DOI：

  10.1016/j.dyepig.2017.09.045

文献信息

• 一种基于二氟硼氧基香豆素的SO2比率型荧光 探针
  申请人：济南大学

  公开号：CN109232626B

  公开（公告）日：2020-08-21

  本发明提供了一种基于二氟硼氧基香豆素的SO 2 比率型荧光探针，其结构式为： 。以二氟硼氧基香豆素为荧光团，通过亚硫酸氢盐或亚硫酸盐与碳碳双键反应使荧光发射产生蓝移。可根据两个波长下的荧光变化检测亚硫酸氢盐或亚硫酸盐的存在。可用于检测溶液和细胞内亚硫酸（氢）盐。
• Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core
  作者：Vladyslav Polishchuk、Andrii Kulinich、Eduard Rusanov、Mykola Shandura

  DOI：10.1021/acs.joc.1c00138

  日期：2021.4.2

  ring is ever more used for creating bright polymethine-type fluorophores for the visible and NIR range. Here, we report the synthesis and spectral properties of a series of dianionic cyanine dyes of the rare A1–π–A−π–A1 type, with the central dioxaborine ring (A) embedded into the polymethine chain and various electron-acceptor terminal groups A1. Depending on the nature of the end group, the maxima of

  β-二酮硼酸二氟硼环越来越多地用于在可见光和NIR范围内生成明亮的聚次甲基型荧光团。在这里，我们报告了一系列稀有的A 1 –π–A–π–A 1类型的双阴离子花青染料的合成和光谱性质，其中心二氧杂硼啉环（A）嵌入聚次甲基链和各种电子受体中端子组A 1。根据端基的性质，其强度最大（最大消光度为380 000 M –1 cm –1））和窄的长波吸收带在530-770 nm的范围内。它们的吸收和荧光带几乎像镜子一样，其特征是弱溶剂溶变色。仅当从极性非质子传递溶剂变为甲醇时，才观察到明显的七色移。设计的双阴离子染料在可见光范围内的荧光量子产率高达92％，即使对于NIR染料，在DMF中也观察到18-37％的值。
• Red-emitting NLOphoric carbazole-coumarin hybrids - Synthesis, photophysical properties and DFT studies
  作者：Abhinav B. Tathe、Nagaiyan Sekar

  DOI：10.1016/j.dyepig.2016.02.026

  日期：2016.6

  corresponding hybrids. The BF2-complexes of the 4-hydroxy-3-acetyl-coumarin derivatives were reacted to give the coumarin-carbazole hybrids. The molecules synthesized emit in the red region. Their photophysical properties were studied in various solvents of different polarity. The solvent polarity function plots were studied and show linearity. The introduction of two units of coumarin core on carbazole

  已知咔唑核是非常有效的供体，并且可以通过推动发色体系中的电子来协助香豆素核实现红色发射。9-乙基-9H-咔唑-3-咔甲醛和9-乙基-9H-咔唑-3,6-二甲醛与3-乙酰基-4-羟基香豆素和7-（N，N-二乙基氨基）-3-反应乙酰-4-羟基香豆素可得到相应的杂种。高炉2-使4-羟基-3-乙酰基-香豆素衍生物的复合物反应，得到香豆素-咔唑杂化物。合成的分子在红色区域发射。在不同极性的各种溶剂中研究了它们的光物理性质。研究了溶剂极性函数图并显示出线性。在咔唑上引入两个香豆素核可提高染料的摩尔消光系数。BF 2络合提高了分子的量子效率和非线性光学性质。
• Ultrafast electron-transfer in a fully conjugated coumarin-ferrocene donor-acceptor dyads
  作者：Alex J. King、Yuriy V. Zatsikha、Tanner Blessener、Forrest Dalbec、Philip C. Goff、Mathew Kayser、David A. Blank、Yuriy P. Kovtun、Victor N. Nemykin

  DOI：10.1016/j.jorganchem.2019.03.004

  日期：2019.5

  investigated by steady-state fluorescence and ultrafast transient absorption spectroscopy methods. Selective photoexcitation of the coumarin core was followed by ultrafast electron transfer from the ferrocene fragment, resulting in formation of a charge-separated Fc+-coumarin-. state. This charge-separated state undergoes ultrafast ground state recovery in 20–25 ps, shortening the excited state lifetime of the

  制备了一系列完全共轭的含二茂铁的香豆素和B，O螯合的香豆素，并通过多种光谱法（UV-vis，NMR和质谱），电化学（CV和DPV）和光谱电化学方法进行了表征。通过稳态荧光和超快速瞬态吸收光谱法研究了目标化合物的光物理性质。对香豆素核心进行选择性光激发，然后从二茂铁片段进行超快电子转移，导致形成电荷分离的Fc + -香豆素-。状态。这种电荷分离态在20-25 ps内经历了超快的基态恢复，使有机香豆素前体的激发态寿命（1.2-1.5 ns）缩短了近两个数量级。实验（稳态荧光氧化滴定）和理论DFT和TDDFT计算支持了电荷分离态的形成。
• NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies
  作者：Abhinav B. Tathe、Nagaiyan Sekar

  DOI：10.1007/s10895-015-1733-8

  日期：2016.3

  The red emitting dyes were synthesized by employing coumarin core as a donor and boron-bonded coumarin as an acceptor. 7-(N,N-Diethylamino)-coumarin 3-aldehyde was reacted with 3-acetyl-4-hydroxy-coumarin, 7-(N,N-diethylamino)-3-acetyl-4-hydroxy-coumarin and 3-acetyl-4-hydroxy-1-methyl-quinolone to form the corresponding chalcones. The synthesized chalcones were though red shifted as compared to the parent coumarin, and were not emitting in red region. The BF2-complexation was used as a tool to introduce a red shift in the molecules. The BF2-complexes synthesized were found to be red emitting and show higher one photon absorption cross section. The solvatochromism shown by these dyes was studied in the light of solvent polarity parameters. DFT calculations were used to understand the photophysical properties of the synthesized dyes. NLO properties of the dyes were estimated by solvatochromic and computational methods. All the molecules synthesized were characterised with the HRMS and NMR spectral Analysis.

  采用香豆素核作为供体，硼键香豆素作为受体合成红色发光染料。 7-(N,N-二乙氨基)-香豆素3-醛与3-乙酰基-4-羟基-香豆素、7-(N,N-二乙氨基)-3-乙酰基-4-羟基-香豆素和3-乙酰基反应-4-羟基-1-甲基-喹诺酮形成相应的查耳酮。与母体香豆素相比，合成的查耳酮虽然发生红移，但不在红色区域发射。 BF2 络合被用作在分子中引入红移的工具。发现合成的 配合物发射红光并显示出更高的单光子吸收截面。根据溶剂极性参数研究了这些染料显示的溶剂化变色现象。 DFT 计算用于了解合成染料的光物理性质。通过溶剂化显色和计算方法评估了染料的 NLO 特性。所有合成的分子均通过 HRMS 和 NMR 光谱分析进行表征。