bis(3,3',4,4',5,5'-hexamethyldipyrroylmethenate)zinc(II) | 55672-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(3,3',4,4',5,5'-hexamethyldipyrroylmethenate)zinc(II)
• 英文别名: zinc(II)(3,3',4,4',5,5'-hexamethyl-2,2'-dipyrrolylmethene)₂；Zn(3,3',4,4',5,5'-hexamethyl-2,2'-dipyrrolylmethene)₂；Zn[3,3',4,4',5,5'-hexamethyldipyrrolylmethene(-1H)]2；Zn(3,3',4,4',5,5'-hexamethyldipyrrolylmethene-2,2'(-1H))2；[Zn(3,3',4,4',5,5'-hexamethyl-2,2'-dipyrrolylmethene(-H))2]
• CAS: 55672-01-0
• 化学式: C₃₀H₃₈N₄Zn
• 分子量: 520.049
• InChiKey: CXLMEYJIGJTGHJ-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  bis(3,3',4,4',5,5'-hexamethyldipyrroylmethenate)zinc(II) 以 neat (no solvent) 为溶剂， 生成 zinc(II) oxide
  参考文献：
  名称：

  Chernova; Berezin; Antina, Russian Journal of Physical Chemistry, 2003, vol. 77, # 6, p. 896 - 900

  摘要：

  DOI：
• 作为产物：
  描述：

  zinc(II) acetate dihydrate 、 2,3,4-Trimethyl-5-[(3,4,5-trimethyl-2H-pyrrol-2-ylidene)methyl]-1H-pyrrole hydrobromide (1:1) 以 N,N-二甲基甲酰胺 为溶剂， 生成 bis(3,3',4,4',5,5'-hexamethyldipyrroylmethenate)zinc(II)
  参考文献：
  名称：

  Dipyrromethene as multifunctional sensor towards d-metal cations

  摘要：

  DOI：

  10.1016/j.jphotochem.2024.115687

文献信息

• Dipyrromethene chromo-fluorogenic chemosensors for quantitative detection and express analysis of Zn2+ ions
  作者：Natalia A. Bumagina、Elena V. Antina、Zinaida S. Krasovskaya、Mikhail B. Berezin、Alexander A. Ksenofontov、Anatoly I. Vyugin、Alexander S. Semeikin

  DOI：10.1016/j.molliq.2021.117834

  日期：2022.1

  Hexamethyl-substituted dipyrromethene had high selectivity towards Zn2+ ions over many environmentally relevant ions, and high sensitivity with the detection limit in nanomolar level (4·10–8 mol/L). In terms of the thermodynamic constant and the fluorescence response of the complexation reaction of [ZnL2], as well as the detection limit of Zn2+ ions, dipyrromethene HL2 surpasses many Zn2+ sensors known in the

  合成了二吡咯亚甲基衍生物作为用于定量检测和表达分析 Zn 2+离子的新型发色荧光化学传感器，并对其进行了结构表征。通过紫外-可见光和荧光光谱、摩尔比图和 DFT 计算来评估二吡咯甲烯对Zn 2+的传感过程。由于[ZnL 2 ]配合物的形成，Zn(AcO) 2与二吡咯亚甲基在DMF溶液中的络合伴随着电子吸收光谱中显着的红移和增色效应。在吸收和理论研究的基础上提出了 1:2 (Zn:HL) 结合模式。Zn(AcO) 2的络合常数(lg K o )dipyrromethenes 为 8.1 到 10.9，这意味着 dipyrromethenes 作为 Zn 2+ 的选择性化学传感器的潜力。首次表明六甲基取代的二吡咯亚甲基可以通过由 Zn 2+引起的显着（近 100 倍）“关-开”荧光响应识别DMF 溶液中的Zn 2+离子，并且可见颜色从黄色变为亮绿色在由 [ZnL 2 ]形成诱导的紫外线照射下。六甲基取代的二吡咯亚甲基对
• Influence of structural factors and medium properties on the fluorescence of alkyl and halogen substituted zinc(II) dipyrromethenates
  作者：Ekaterina N. Nuraneeva、Galina B. Guseva、Elena V. Antinа、Anatoly I. V'yugin

  DOI：10.1016/j.molliq.2019.112026

  日期：2020.1

  functionalization features of dipyrromethene ligands on the fluorescence quenching efficiency of luminophores [ZnL2] was discussed. Found that [ZnL2] with dibromo-substituted ligands exhibits the highest sensitivity of the fluorescence characteristics to the presence of proton- and electron donor analytes in comparison with alkyl substituted analogues. The obtained results allow to offer zinc(II) dipyrromethenates

  在环己烷与质子和给电子助溶剂（丙酮，乙醇）的各种添加剂的二元混合物中，组成为[ZnL 2 ]的烷基和卤素取代的二吡咯烷酮（HL）的一系列锌（II）配合物的光谱研究结果提出了N，N-二甲基甲酰胺，吡啶，二乙胺和三乙胺。讨论了助溶剂的极性和供电子能力以及二吡咯亚甲基配体的功能化特征对发光体[ZnL 2 ]的荧光猝灭效率的影响。发现[ZnL 2与烷基取代的类似物相比，具有二溴取代的配体的化合物对质子和电子供体分析物的存在表现出最高的荧光特性敏感性。将得到的结果允许提供锌（II）dipyrromethenates如新，高灵敏度和选择性荧光 «开-关» 的O-和传感器Ñ含毒物（最多〜8∙10 -6 摩尔/升）在有机介质中。
• Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II)
  作者：Mikhail B. Berezin、Sofya A. Dogadaeva、Elena V. Antina、Mikhail M. Lukanov、Alexander A. Ksenofontov、Alexander A. Semeikin

  DOI：10.1016/j.dyepig.2022.110215

  日期：2022.6

  non-polar solvents to polar. Unsymmetrically substituted zinc(II) dipyrromethenates are characterized by low value of the fluorescence quantum yield, the fluorescence almost completely quenching in weakly polar and polar solvents. It is found that the unsymmetrically substitution increases photostability of boron(III) and zinc(II) complexes but decreases their thermal stability in solid state.

  以高收率合成了不对称取代的硼（III）和锌（II）二吡咯酸，并给出了它们的物理化学研究结果。根据分子结构，对一系列各种有机溶剂中的发光特性、光稳定性和热稳定性进行了对比分析。首次确定在一个吡咯片段的 α-、β-或 β'-位不存在甲基基团会不同地改变五甲基-二吡咯亚甲基配体和配合物的性质。结果表明，一个吡咯循环的未取代的 α- 或 β- 位会导致强吸收带的最大值和自由 β'-位向红移。一般情况下，荧光BODIPY的量子产率达到99%，几乎不依赖于溶剂性质。然而，在一个 α 位未取代的 BODIPY 在从非极性溶剂变为极性溶剂时，荧光量子产率急剧下降。不对称取代的二吡咯酸锌(II) 的特点是荧光量子产率低，在弱极性和极性溶剂中荧光几乎完全猝灭。发现不对称取代增加了硼（III）和锌（II）配合物的光稳定性，但降低了它们在固态下的热稳定性。
• Thermal properties of ligands, salts and metal complexes of linear oligopyrroles
  作者：E. V. Antina、G. B. Gusev、E. V. Rumyantsev、N. A. Dudina

  DOI：10.1134/s1070363209090163

  日期：2009.9

  The effect of structure on the thermal properties of dipyrrolylmethanes, dipyrrolylmethenes, bis (dipyrrolylmethenes), their salts, and chelates is analyzed proceeding from the results of thermogravimetric analysis. The common tendency is a decrease in the thermal stability of compounds with a disturbed symmetry of alkyl substitution of ligands and with a higher degree of their alkylation, with the increased size of alkyl substituents, with the nitrogen atom in the five-member cycles replaced by S or O. The opposite effect occurs at the change in the mode of attaching methylene spacer in going from 2,2'- to 3,3'-bis(dipyrrolylmethenes). The effects of the themostabilization of the ligands of linear oligopyrroles in the composition of chelates and HBr salts are evaluated quantitatively.
• Complex formation of Cu(II), Ni(II), Zn(II), Co(II), and Cd(II) acetates with 3,3′,4,4′,5,5′-hexamethyldipyrrolylmethene
  作者：G. B. Guseva、E. V. Antina、A. I. V’yugin、A. E. Loginova

  DOI：10.1134/s1070328408080071

  日期：2008.8

  The reactions of complex formation of Cu(II), Co(II), Zn(II), Ni(II), and Cd(II) acetates with 3,3',4,4'5,5'-hexamethyl-2,2'-dipyrrolylmethene (HL) in DMF were studied by the electronic spectroscopy and calorimetric titration methods at 298.15 K. The main products of the above reactions are [ML2] chelates. In the case of Cu and Ni salts, the process occurs through the spectrally recorded stage of formation of the heteroligand [ML(AcO)] complexes. The reaction with Cd acetate terminates at the stage of the heteroligand complex formation due to the large radius and decreasing electron affinity of the Cd2+ ion. The effect of the metal nature appears in the increasing thermodynamic stability of single-type complexes in the series [ML2]: Ni(II) < Zn(II) < Co(II) < Cu(II) and [ML(AcO)]: Cd(II) < Ni(II) < Cu(II).

表征谱图