2-[(3,5-diphenyl-2H-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1H-pyrrole | 13401-33-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-[(3,5-diphenyl-2H-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1H-pyrrole
• 英文别名: 2-[(3,5-Diphenyl-2h-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1h-pyrrole；2-[(3,5-diphenyl-1H-pyrrol-2-yl)methylidene]-3,5-diphenylpyrrole
• CAS: 13401-33-7
• 化学式: C₃₃H₂₄N₂
• 分子量: 448.567
• InChiKey: YYQCPYDRARPYOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(3,5-diphenyl-2H-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1H-pyrrole 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4,4-difluoro-1,3,5,7-tetraphenyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  The computational and experimental investigations of photophysical and spectroscopic properties of BF2 dipyrromethene complexes

  摘要：

  The electronic excited states of BF2 dipyrromethene (2BrDPM, DPMI, DPMII, PM567 and 4PhDPM) complexes were investigated using the extended multi-configuration quasi-degenerate at the second order of perturbation theory (XMCQDPT2) and the second-order approximate coupled-cluster (CC2) methods. The excitation energies calculated by CC2 are significantly overestimated by 0.42-0.59 eV because of the substantial contributions of double excitation levels to excited states (>10%). However, the calculated XMCQDPT2 excitation energies agree well with experimental ones within the accuracy 0.11-0.20 eV. The very low lasing efficiency (7.8-8.4%) of 4PhDPM compound was explained by the T-1 -> T-4 and T-1 -> T-5 reabsorptions at XMCQDPT2 level of theory. The molecular photonics of pyrromethenes are studied using a combination of the first-principle and semi-empirical calculations. The main mechanism for the deactivation of the energy of the first singlet excited electronic state is the radiative electronic transition for DPMI, DPMII, PM567 and 4PhDPM compounds. Also, the main mechanism for the quenching of fluorescence in considered complexes (except DPMII compound) is the internal conversion. The processes of the internal conversion and intersystem crossing compete with each other in DPMII compound. The measured and calculated fluorescence quantum yields agree well for all considered molecules. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.08.042
• 作为产物：
  描述：

  3,5-diphenyl-3,4-dihydro-2H-pyrrole 在 selenium 作用下， 生成 2-[(3,5-diphenyl-2H-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1H-pyrrole
  参考文献：
  名称：

  157. 2：4-二芳基吡咯。第二部分：蛋氨酸

  摘要：

  DOI：

  10.1039/jr9430000596

文献信息

• Synthesis, Spectral-Luminescent Properties, and Photostability of Zn(II) Complexes With Dipyrrins Modified by the Periphery and meso-Spacer
  作者：N. A. Dudina、A. Yu. Nikonova、Ye. V. Antina、M. B. Berezin、A. I. Vyugin

  DOI：10.1007/s10593-014-1426-2

  日期：2014.3

  characterization was performed for the homoleptic zinc(II) chelates with dipyrrins containing four methyl or aryl substituents in the pyrrole rings and methine group or nitrogen atom as meso-spacer. It was shown that zinc dipyrrinates with substituted pyrrole rings and a methene spacer exhibited an intense fluorescence in nonpolar media. The phenyl-substituted complex had an order of magnitude stronger fluorescence

  对均一的锌（II）螯合物进行了比较的光谱发光表征，其中吡咯类在吡咯环中含有四个甲基或芳基取代基，次甲基或氮原子作为中间隔基。结果表明，具有取代的吡咯环和亚甲基间隔基的二吡啶锌锌在非极性介质中表现出强烈的荧光。苯基取代的配合物比甲基取代的类似物具有增强一个数量级的荧光。从亚甲基间隔基更改为氮原子会导致电子吸收光谱发生明显的红移（最高达64 nm），并且螯合物完全失去了荧光性能。建立了螯合配体结构对锌（II）配合物光稳定性的影响。
• Effect of Aryl-, Halogen-, and Ms-Aza-Substitution on the Luminescent Properties and Photostability of Difluoroborates of 2,2′-Dipyrrometenes
  作者：Anna Yu. Kritskaya、Mikhail B. Berezin、Elena V. Antina、Anatoly I. Vyugin

  DOI：10.1007/s10895-019-02403-2

  日期：2019.7

  to 5–20%. The stability of 2,2′-dipyrromethenes difluoroborates to oxidative destruction under the influence of UV irradiation in cyclohexane solutions was evaluated. It has been shown that symmetric aryl substitution in pyrrole cycles of dipyrromethene significantly increases the photostability of the corresponding compounds as compared to alkyl-substituted analogs and is an effective method of obtaining

  合成了具有烷基，苯基和卤素取代的2,2'-二吡咯烷酮（BODIPY）和内消旋氮杂双吡咯烷酮（ms-aza-BODIPY）的硼（III）配合物。分析了所获得的配位化合物与其发光特性的结构关系。与烷基取代的类似物相比，丙烯酸化的BODIPY对与溶剂的粒子间相互作用更敏感，从而导致量子产率最多降低40％。在BODIPY分子中引入苯基​​取代基会使第一个吸收带发生红移，显着（32-37 nm）增加了发射光谱的斯托克斯位移，但降低了S 0  →S 1的可能性与烷基化配合物相比，电子跃迁。与BODIPY相比，用氮取代次甲基碳原子会导致ms-aza-BODIPY荧光猝灭，最高可达5-20％。评价了2,2'-吡咯并蒽二氟硼酸盐在环己烷溶液中的紫外线照射下对氧化破坏的稳定性。已经显示，与烷基取代的类似物相比，在二吡咯亚甲基的吡咯循环中的对称芳基取代显着增加了相应化合物的光稳定性，并且是获得具有实际有用性能的
• A New Sensitive and Selective Off-On Fluorescent Zn2+ Chemosensor Based on 3,3′,5,5′-Tetraphenylsubstituted Dipyrromethene
  作者：Natalia A. Bumagina、Elena V. Antina、Anna Yu. Nikonova、Mikhail B. Berezin、Alexander A. Ksenofontov、Anatoly I. Vyugin

  DOI：10.1007/s10895-016-1890-4

  日期：2016.11

  highly sensitive and selective Off-on fluorescent colorimetric chemosensor for Zn2+ based on the chelation-enhanced fluorescence (CHEF) effect. The reaction of dipyrromethene ligand with Zn2+ induces the formation of the [ZnL2] complex, which exhibits the increasing fluorescence in 120 fold compared with ligand in the propanol-1/cyclohexane (1:30) binary mixture. The Zn2+ detection limit was 1.4 × 10−7

  3,3'，5,5'-四苯基-2,2'-二吡咯亚甲基被描述为基于螯合增强荧光（CHEF）效应的Zn 2+的高灵敏度和选择性Off-on荧光比色化学传感器。二吡咯亚甲基配体与Zn 2+的反应诱导了[ZnL 2 ]配合物的形成，与丙醇-1 /环己烷（1:30）二元混合物中的配体相比，荧光显示增加了120倍。中的Zn 2+检测限为1.4×10 -7 М. UV-Vis和荧光光谱研究表明，二吡咯亚甲基传感器对Zn 2+阳离子的选择性高于其他金属离子（Na +，Mg 2+，Co 2 +，Ni 2 +，Fe 3+，Cu 2 +，Mn 2 +，Cd 2+和Pb 2 +），Hg 2+除外。
• Cook; Majer, Journal of the Chemical Society, 1944, p. 482,485
  作者：Cook、Majer

  DOI：——

  日期：——
• Synthesis, spectral-luminescent properties of B(III) and Zn(II) complexes with alkyl- and aryl-substituted dipyrrins and azadipyrrins
  作者：E. V. Antina、M. B. Berezin、N. A. Dudina、S. L. Burkova、A. Yu. Nikonova

  DOI：10.1134/s0036023614100027

  日期：2014.10

  Effect of complexing atom, molecular structure of dipyrrolylmethene and its aza analog on spectral-luminescent properties of heteroleptic boron(III) and homoleptic zinc(II) complexes with 3,3',5,5'-tetramethyl-2,2'-dipyrrolylmethene, 3,3',5,5'-tetraphenyl-2,2'-dipyrrolylmethene, and 3,3',5,5'-tetraphenyl-ms-aza-2,2'-dipyrrolylmethene in organic solvent solutions was studied. The complexes were found to exhibit strong chromophore (lambda = 350-690 nm, E > similar to 10(5) L/mol cm) and fluorescent properties. Quantum yield (gamma(fl)) for fluoroborate complexes reaches 100% and is weakly dependent on medium nature. The value of gamma(fl) for phenyl- and alkyl-substituted zinc(II) dipyrrolylmethenates in nonpolar solvents is not higher 0.3 and 0.03, respectively; complete fluorescence quenching is observed in electron-donating solvents. Aza-substitution at the meso spacer causes considerable shift of electronic absorption and fluorescence spectra to the red region but completely quenches fluorescence of zinc(II) chelates and decreases gamma(fl) of boron(III) complex to 0.04.