4’-(3,4-ethylenedioxythiophene)-2,2’:6’,2’’-terpyridine | 1421943-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4’-(3,4-ethylenedioxythiophene)-2,2’:6’,2’’-terpyridine
• 英文别名: 4′-(3,4-ethylenedioxythiophene)-2,2′:6′,2″-terpyridine；4-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2,6-dipyridin-2-ylpyridine
• CAS: 1421943-91-0
• 化学式: C₂₁H₁₅N₃O₂S
• 分子量: 373.435
• InChiKey: UCPJOPYZJNMUFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cobalt(II) chloride hexahydrate 、 4’-(3,4-ethylenedioxythiophene)-2,2’:6’,2’’-terpyridine 在 ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以84%的产率得到bis-[4’-(3,4-ethylenedioxythiophene)-2,2’ :6’,2’’-terpyridine] cobalt(II) bis-hexafluorophosphate
  参考文献：
  名称：

  Synthesis of π-Conjugated 2,2:6′,2″-Terpyridine-Substituted Oligomers Based on 3,4-Ethylenedioxythiophene

  摘要：

  Dissymmetric pi-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in basic media or, for the longest oligomers, direct C H bond arylation. They have a low HOMO-UMO gap and are easily oxidized at low potentials. Upon complexation with cobalt(II) and iron(II) they yield new hybrid materials that can be used in various applications ranging from photovoltaics to spintronics.

  DOI：

  10.1021/ol303512f
• 作为产物：
  描述：

  3,4-乙烯二氧噻吩 在 氨 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 68.0h， 生成 4’-(3,4-ethylenedioxythiophene)-2,2’:6’,2’’-terpyridine
  参考文献：
  名称：

  Synthesis of π-Conjugated 2,2:6′,2″-Terpyridine-Substituted Oligomers Based on 3,4-Ethylenedioxythiophene

  摘要：

  Dissymmetric pi-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in basic media or, for the longest oligomers, direct C H bond arylation. They have a low HOMO-UMO gap and are easily oxidized at low potentials. Upon complexation with cobalt(II) and iron(II) they yield new hybrid materials that can be used in various applications ranging from photovoltaics to spintronics.

  DOI：

  10.1021/ol303512f

文献信息

• Tuning the photophysical properties of 4′-substituted terpyridines – an experimental and theoretical study
  作者：Anna Maroń、Agata Szlapa、Tomasz Klemens、Slawomir Kula、Barbara Machura、Stanisław Krompiec、Jan Grzegorz Małecki、Anna Świtlicka-Olszewska、Karol Erfurt、Anna Chrobok

  DOI：10.1039/c6ob00038j

  日期：——

  Several 2,2′:6′,2′′-terpyridines substituted in the 4′-position were synthesized and their photophysical properties were investigated by absorption and photoluminescence spectroscopy in dilute solutions and solid state. The studies confirmed that the absorption and emission wavelengths, fluorescence quantum yields and lifetimes of 1-R1–16 are strongly structure-related, demonstrating a decisive role

  合成了几个在4'-位取代的2,2'：6'，2''-吡啶吡啶，并在稀溶液和固态下，通过吸收和光致发光光谱研究了它们的光物理性质。研究证实1-R 1-16的吸收和发射波长，荧光量子产率和寿命与结构密切相关，这表明取代基的性质在确定4'-官能化的吡啶的光物理性质中起着决定性的作用。此外，对1-R 1-16进行了密度泛函理论（DFT）计算，以了解其电子结构和光谱性质。
• Rhenium(<scp>i</scp>) terpyridine complexes – synthesis, photophysical properties and application in organic light emitting devices
  作者：Tomasz Klemens、Anna Świtlicka-Olszewska、Barbara Machura、Marzena Grucela、Ewa Schab-Balcerzak、Karolina Smolarek、Sebastian Mackowski、Agata Szlapa、Slawomir Kula、Stanisław Krompiec、Piotr Lodowski、Anna Chrobok

  DOI：10.1039/c5dt04093k

  日期：——

  The structural and photophysical characterization of new Re(i) complexes was reported.

  报道了新的Re(i)配合物的结构和光物理特性表征。
• Impact of Counteranion on Reversible Spin-State Switching in a Series of Cobalt(II) Complexes Containing a Redox-Active Ethylenedioxythiophene-Based Terpyridine Ligand
  作者：Subrata Ghosh、Sounak Ghosh、Sujit Kamilya、Subhankar Mandal、Sakshi Mehta、Abhishake Mondal

  DOI：10.1021/acs.inorgchem.2c02313

  日期：2022.10.31

  (EDOT)-terpyridine-based tridentate ligand and cobalt(II) unit with different counteranions has led to a series of new cobalt(II) complexes [Co(L)2](X)2 (X = BF4 (1), ClO4 (2), and BPh4 (3)) (L = 4′-(3,4-ethylenedioxythiophene)-2,2′:6′,2″-terpyridine). The impact of various counteranions on stabilization and spin-state switching of the cobalt(II) center was explored through detailed magneto-structural

  具有氧化还原活性的乙烯二氧噻吩 (EDOT)-三联吡啶基三齿配体和具有不同抗衡阴离子的钴 (II) 单元的自组装产生了一系列新的钴 (II) 配合物 [Co( L ) 2 ](X) 2 (X = BF 4 ( 1 )、ClO 4 ( 2 ) 和 BPh 4 ( 3 )) ( L= 4'-(3,4-乙烯二氧噻吩)-2,2':6',2"-三联吡啶)。通过使用变温单晶 X 射线衍射、磁性、光谱、电化学和光谱电化学研究的详细磁结构研究，探索了各种反阴离子对钴 (II) 中心的稳定性和自旋态转换的影响。所有三个配合物1 – 3均由两个​​L配体以双子午线方式提供的同构双阳离子扭曲八面体 CoN 6配位环境和 BF 4 –、ClO 4 –和 BPh 4 –分别作为抗衡阴离子组成。复合体2与 ClO 4 –抗衡阴离子在低自旋 (LS) ( S = 1/2) 和高自旋 (HS) ( S = 3/2) 状态
• Synthesis, X-ray Studies and Photophysical Properties of Iridium(III) Complexes Incorporating Functionalized 2,2′:6′,2″ Terpyridines and 2,6-Bis(thiazol-2-yl)pyridines
  作者：Bartosz Zowiślok、Anna Świtlicka、Anna Maroń、Mariola Siwy

  DOI：10.3390/molecules29112496

  日期：——

  iridium(III) triimine complexes incorporating 2,2′:6′,2″-terpyridine (terpy) and 2,6-bis(thiazol-2-yl)pyridine (dtpy) derivatives were successfully designed and synthesized to investigate the impact of the peripheral rings (pyridine, thiazole) and substituents (thiophene, bithiophene, EDOT) attached to the triimine skeleton on their photophysical properties. The Ir(III) complexes were fully characterized

  成功设计并合成了一系列包含 2,2':6',2"-三联吡啶 (terpy) 和 2,6-双(噻唑-2-基)吡啶 (dtpy) 衍生物的铱(III)三亚胺配合物，用于研究连接到三亚胺骨架上的外围环（吡啶、噻唑）和取代基（噻吩、联噻吩、EDOT）对其光物理性质的影响。使用 IR、1H、元素分析和单晶 X 射线分析对 Ir(III) 配合物进行了全面表征。使用 TGA 测量来评估它们的热性能。在 298 和 77 K 的溶液中研究了 [IrCl3L1–6] 的光致发光光谱。实验研究伴随着 DFT/TDDFT 计算。通过电子吸收和发射详细研究了合成的三亚胺配体和Ir(III)配合物的光物理性质。在溶液中，它们表现出的光致发光量子产率范围为 1.27% 至 5.30%，具体取决于化学结构。实验研究包括DFT/TDDFT计算。使用电子吸收和发射技术对合成的三亚胺配体和Ir(III)配合物的光物理性质进