4,4'-bis((E)-styryl)-2,2'-bipyridine | 825621-06-5

• 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: 4,4'-bis((E)-styryl)-2,2'-bipyridine
• 英文别名: (E,E′)-4,4′-bisstyryl-2,2′-bipyridine；(E,E′)-4,4'-bisstyryl-2,2′-bipyridine；4,4'-di((E)-styryl)-2,2'-bipyridine；(E,E’)-4,4'-bisstyryl-2,2'-bipyridine；4,4'-distyryl-2,2'-bipyridine；4-[(E)-2-phenylethenyl]-2-[4-[(E)-2-phenylethenyl]pyridin-2-yl]pyridine
• CAS: 825621-06-5
• 化学式: C₂₆H₂₀N₂
• 分子量: 360.458
• InChiKey: OFZKDHVEYWXZKM-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  水合三氯化钌 、 4,4'-bis((E)-styryl)-2,2'-bipyridine 在 hydroquinone 、 LiCl 作用下， 以 乙醇 为溶剂， 生成 [RuCl2(4,4'-distyryl-2,2'-bipyridine)2]
  参考文献：
  名称：

  Influence of the Nature of the Absorption Band on the Potential Performance of High Molar Extinction Coefficient Ruthenium(II) Polypyridinic Complexes As Dyes for Sensitized Solar Cells

  摘要：

  When tested in solar cells, ruthenium polypyridinic dyes with extended pi systems show an enhanced light-harvesting capacity that is not necessarily reflected by a high (collected electrons)/(absorbed photons) ratio. Provided that metal-to-ligand charge transfer bands, MLCT, are more effective, due to their directionality, than intraligand (IL) pi-pi* bands for the electron injection process in the solar cell, it seems important to explore and clarify the nature of the absorption bands present in these types of dyes. This article aims to elucidate if all the absorbed photons of these dyes are potentially useful in the generation of electric current. In other words, their potentiality as dyes must also be analyzed from the point of view of their contribution to the generation of excited states potentially useful for direct injection. Focusing on the assignment of the absorption bands and the nature of the emitting state, a systematic study for a series of ruthenium complexes with 4,4'-distyryl-2,2'-dipyridine (LH) and 4,4'-bis[p-(dimethylamino)-alpha-styryl]-2,2'-bipyridine (LNMe2) "chromophoric" ligands was undertaken. The observed experimental results were complemented with TDDFT calculations to elucidate the nature of the absorption bands, and a theoretical model was proposed to predict the available energy that could be injected from a singlet or a triplet excited state. For the series studied, the results indicate that the percentage of MLCT character to the anchored ligand for the lower energy absorption band follows the order [Ru(deebpy)(2)(LNMe2)](PF6)(2) > [Ru(deebpy)(2)(LH)] (PF6)(2) > [Ru(deebpy)(LH)(2)](PF6)(2), where deebpy is 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine, predicting that, at least from this point of view, their efficiency as dyes should follow the same trend.

  DOI：

  10.1021/ic1020862
• 作为产物：
  描述：

  2,2'-联吡啶-4,4'-二甲醇 在 硫酸 、 potassium tert-butylate 、 氢溴酸 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4,4'-bis((E)-styryl)-2,2'-bipyridine
  参考文献：
  名称：

  以4,4'-双（（E）-苯乙烯基）-2,2'-联吡啶为辅助配体的多金属Ru（II）配合物的合成与表征及其在染料敏化太阳能电池中的应用

  摘要：

  基于4,4'-bis（（E）-styryl）-2,2'-bipyridine（bsbpy）作为染料敏化太阳能电池（DSSC）的辅助配体设计了杂多味Ru（II）配合物（II）增敏剂[Ru（L）（bsbpy）（NCS）2 ] [TBA]（TBA；四丁基铵）是根据[RuCl 2（p- cymene）] 2与苯的典型单锅反应合成的。相应的锚定配体（其中L = 4,4'-二羧基-2,2'-联吡啶（dcbpy），4,4'-双（（E）-羧基乙烯基）-2,2'-联吡啶（dcvbpy），4， 7-二羧基-1,10-菲咯啉（dcphen）或4,7-双（（E）-羧基乙烯基）-1,10-菲咯啉（dcvphen））。新型Ru（II）染料[Ru（L）（bsbpy）（NCS）2] [TBA]将乙烯基间隔基掺入辅助和/或锚定配体中，相对于N719的吸收光谱，在整个UV / VIS区域显示出红移带。bsbpy辅助和dcph

  DOI：

  10.1002/hlca.201800030

文献信息

• Synthesis, crystal structures, optoelectronic properties and resistive memory application of π-conjugated heteroaromatic molecules
  作者：Ming Jia、Yabo Li、Mengmeng Huang、Jung Keun Kim、Yingliang Liu、Yangjie Wu、Shaokui Cao

  DOI：10.1016/j.tet.2020.131471

  日期：2020.9

  binary memory behavior, while DPBT-based device presents no memory property. The experimental results confirm that the introduction of CC bridged bonds into molecules could enhance the molecular interaction, which plays an important role in the molecular arrangement on the thin film, and has a significant contribution to charge transport in memory devices. This work demonstrates that aryl vinyl terminated

  设计并合成了三种基于联噻唑或联吡啶的π共轭小分子DPBT，DEPBT和DEPBPy。在DEPBT和DEPBPy中，中心核和末端苯基通过C C双键连接，而在DPBT中，它们通过C–C单键结合。比较研究了分子结构变化对其晶体结构，光电性能和薄膜形态的影响。此外，它们的电阻记忆性能是首次被研究。无论DEPBT -和DEPBPy为基础的设备表现出典型的二元记忆行为，而基于DPBT的设备没有内存属性。实验结果证实，将C C桥键引入分子中可以增强分子相互作用，这在薄膜上的分子排列中起着重要作用，并且对存储器件中的电荷传输有重要贡献。这项工作表明，芳基乙烯基封端的联噻唑和联吡啶都是有机存储的良好前途候选者。
• Rationally designed ruthenium complexes for 1- and 2-photon photodynamic therapy
  作者：Johannes Karges、Shi Kuang、Federica Maschietto、Olivier Blacque、Ilaria Ciofini、Hui Chao、Gilles Gasser

  DOI：10.1038/s41467-020-16993-0

  日期：——

  The use of photodynamic therapy (PDT) against cancer has received increasing attention over recent years. However, the application of the currently approved photosensitizers (PSs) is limited by their poor aqueous solubility, aggregation, photobleaching and slow clearance from the body. To overcome these limitations, there is a need for the development of new classes of PSs with ruthenium(II) polypyridine

  近年来，针对癌症的光动力疗法（PDT）的使用受到越来越多的关注。但是，目前批准的光敏剂（PSs）的应用受到水溶性差，聚集，光致漂白和从体内清除缓慢的限制。为了克服这些局限性，需要开发新型的带有钌（II）聚吡啶配合物的新型聚苯乙烯。然而，这些化合物通常在生物光谱窗口中缺乏明显的吸收，从而限制了它们在治疗深部或大肿瘤中的应用。为克服此缺点，在计算机上设计了具有（E，E的钌（II）聚吡啶络合物'）-4,4'-双苯乙烯基-2,2'-联吡啶配体显示出令人印象深刻的1和2光子吸收率，其幅度比迄今为止公布的值高。尽管这些化合物在黑暗中无毒，但它们在各种2D单层细胞，3D多细胞肿瘤球体中具有光毒性，并在临床相关的1-Photon和2-Photon激发下能够根除小鼠模型内的多抗性肿瘤。
• [EN] METAL COMPLEXES BEARING BISSTYRYL-BIPYRIDINE LIGAND AND THEIR USE AS PHOTOSENSITIZER AGENT IN ONE AND TWO-PHOTON PHOTODYNAMIC THERAPY<br/>[FR] COMPLEXES MÉTALLIQUES PORTANT UN LIGAND BISSTYRYL-BIPYRIDINE ET LEUR UTILISATION EN TANT QU'AGENT PHOTOSENSIBILISANT DANS UNE THÉRAPIE PHOTODYNAMIQUE À UN ET DEUX PHOTONS
  申请人：PARIS SCIENCES LETTRES QUARTIER LATIN

  公开号：WO2021089644A1

  公开（公告）日：2021-05-14

  The present invention relates to metal complexes bearing at least one (E-E')-4,4'- bisstyryl-2,2'-bipyridine ligand (LIG1) of the following formula (I): or a pharmaceutically acceptable salt and/or solvate thereof. The present invention also relates to pharmaceutical compositions comprising these complexes and at least one pharmaceutically acceptable excipient. The present invention also relates to the use of compounds of formula (I) or pharmaceutical compositions comprising thereof as drug and as photosensitizer agent in photodynamic therapy. The present invention also relates to methods of preparation of said complexes.

  本发明涉及具有至少一个(E-E')-4,4'-双亚基苯基-2,2'-联吡啶配体（LIG1）的金属配合物的以下结构式（I）：或其药学上可接受的盐和/或溶剂。本发明还涉及包括这些配合物和至少一种药学上可接受的赋形剂的制药组合物。本发明还涉及将结构式（I）的化合物或包含其的制药组合物用作药物和光动力疗法中的光敏剂的用途。本发明还涉及所述配合物的制备方法。
• PHOTOELECTRIC CONVERSION DEVICES COMPRISING NOVEL LIGANDS AND SENSITIZERS
  申请人：Nazeeruddin Mohammad

  公开号：US20110303267A1

  公开（公告）日：2011-12-15

  The present invention provides novel dyes for dye sensitized photovoltaic conversion devices. The dyes contain novel anchoring ligands, which have a vinyl or phenylethenyl moiety incorporated in the anchoring bipyridine. Such dyes exhibit an increased molar extinction coefficient and enhanced red response in the visible regions.

  本发明提供了用于染料敏化光伏转换器件的新型染料。这些染料包含新型锚定配体，其中在锚定双吡啶中加入了乙烯基或苯乙烯基。这些染料表现出增加的摩尔消光系数和增强的可见光区域的红色响应。
• Synthesis, Characterisation and Biological Evaluation of π-Extended Fe(II) Bipyridine Complexes as Potential Photosensitizers for Photodynamic Therapy
  作者：Johannes Karges、Gilles Gasser

  DOI：10.1016/j.ica.2019.119196

  日期：2020.1

  Photodynamic therapy (PDT) has received increasing attention over the recent years to treat a variety of cancers. The use of metal complexes as PDT agents is currently a highly investigated alternative due to the attractive chemical and photophysical properties of these compounds. However, most of the metal complexes studied so far are based on rare metals, limiting their use since these metals are neither cheap nor abundant. It would be therefore of high interest to develop compounds based on a cheap, abundant metal. Having this in mind, we designed Fe(II) polypyridine complexes with an absorption in the biological spectral window (600-900 nm) through extension of the pi-system. Importantly, the complexes were found to be stable in human plasma and upon light irradiation. A cytotoxic effect in the micromolar range in the dark and a slight effect upon exposure to irradiation at 480 and 540 nm in cancerous human cervical carcinoma (HeLa) cells was observed.