zinc(II)(3,3',5,5'-tetramethyl-4,4'-diethyl-2,2'-dipyrrolylmethene)₂ | 53504-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: zinc(II)(3,3',5,5'-tetramethyl-4,4'-diethyl-2,2'-dipyrrolylmethene)₂
• 英文别名: Zn(3,3',5,5'-tetramethyl-4,4'-diethyl-2,2'-dipyrrolylmethene)₂；bis(4,4'-diethyl-3,3',5,5'-tetramethyldipyrroylmethenate)zinc(II)；bis(κ2-4,4'-diethyl-3,3',5,5'-tetramethyldipyrrinato)zinc；Zn(DPM)2；Zn(4,4'-diethyl-3,3',5,5'-tetramethyl-2,2'-dipyrrolylmethene(-1H))2；Zn(3,3',5,5'-tetramethyl-4,4'-diethyldipyrrolylmethene-2,2'(-1H))2；Zn(3,3',5,5'-tetramethyl-4,4'-diethyldipyrrolylmethene(-1H))2；zinc;(2Z)-4-ethyl-2-[(4-ethyl-3,5-dimethylpyrrol-1-id-2-yl)methylidene]-3,5-dimethylpyrrole
• CAS: 53504-73-7
• 化学式: C₃₄H₄₆N₄Zn
• 分子量: 576.156
• InChiKey: IZYCAJKRKYPQMD-KNGYMQEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四苯基卟啉 、 zinc(II)(3,3',5,5'-tetramethyl-4,4'-diethyl-2,2'-dipyrrolylmethene)₂ 以 N,N-二甲基甲酰胺 为溶剂， 生成 zinc tetraphenylporphyrin
  参考文献：
  名称：

  10.1007/s11502-008-3009-6

  摘要：

  DOI：

  10.1007/s11502-008-3009-6
• 作为产物：
  描述：

  2,4,8,10-tetramethyl-3,9-diethyldipyrrolyl-5,7-methene 、 zinc diacetate 以 N,N-二甲基甲酰胺 为溶剂， 生成 zinc(II)(3,3',5,5'-tetramethyl-4,4'-diethyl-2,2'-dipyrrolylmethene)₂
  参考文献：
  名称：

  Trends in formation and stability of homo- and heteroligand d-metal complexes with 2,2′-dipyrrolylmethenes in dimethylformamide

  摘要：

  The reactions of symmetric and nonsymmetric alkyl-substituted 2,2'-dipyrrolylmethenes with Cu(II), Ni(II), Co(II), Zn(II), Cd(II), and Hg(II) acetates in dimethylformamide solutions at 298.15 K were studied. The formation of hetero- and homoligand complexes was observed in the systems studied depending on the concentration conditions and the nature of the complexing metal. The stepped and complete constants of formation for metal complexes were determined. The key trends of the influence of the metal and ligand nature on the stabilization of the complexes were established.

  DOI：

  10.1134/s0036023609110084

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
• The first series of alkali dipyrrinato complexes
  作者：Adeeb Al-Sheikh Ali、Judy Cipot-Wechsler、Sarah M. Crawford、Omar Selim、Rhonda L. Stoddard、T. Stanley Cameron、Alison Thompson

  DOI：10.1139/v09-180

  日期：2010.8

  The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, the intermolecular distance between the two nitrogen atoms and thus the κ²-N,N-bidentate bite angle was altered, as confirmed by comparison of crystallographic structures of dipyrrin free-bases in the solid-state. The mode of bonding varies as the ionic radius of the metal ion increases: solid-state structures reveal lithium to be accommodated in the plane of the dipyrrinato unit, whilst sodium is accommodated out of plane. The reactivity of analogous lithium, sodium, and potassium dipyrrinato complexes increases as the ionic radius of the metal ion increases, in keeping with the concept that the complexes tend towards an increasingly ionic nature as the size of the alkali metal increases.

  报告了第一个碱二吡咯烷酮配合物系列，包括中位未取代和中位芳基取代衍生物的锂、钠和钾盐。通过改变中位取代基，两个氮原子之间的分子间距发生了变化，从而改变了κ2-N,N-二齿咬合角，这一点通过比较二吡咯啉游离基在固态下的晶体结构得到了证实。成键模式随金属离子的离子半径增大而变化：固态结构显示锂被容纳在二吡咯烷单元的平面内，而钠则被容纳在平面外。类似的锂、钠和钾二吡咯烷酮络合物的反应性随着金属离子的离子半径的增加而增加，这与络合物的离子性随着碱金属尺寸的增加而增加这一概念是一致的。
• 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。
• Synthesis and Reactivity of a Dipyrrinatolithium Complex
  作者：Judy Cipot-Wechsler、Adeeb Al-Sheikh Ali、Erin E. Chapman、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/ic701369h

  日期：2007.12.1

  The synthesis and characterization of the first dipyrrinato-alkalimetal complex is reported herein. The novel reactivity of this lithium complex is demonstrated in the preparation, isolation, and characterization of a heteroleptic zinc(II) complex in high yield.
• 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.