trans-2-[p-formylstyryl]benzimidazole | 63405-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: trans-2-[p-formylstyryl]benzimidazole
• 英文别名: trans-2-[2-(4-formylphenyl)ethenyl]benzimidazole；trans-2-(p-Formylstyryl)benzimidazole；4-[(E)-2-(1H-benzimidazol-2-yl)ethenyl]benzaldehyde
• CAS: 63405-74-3
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: ZPIZFNCWXWQTFT-MDZDMXLPSA-N

物化性质

• 熔点：
  178.4-179.6 °C(Solv: ligroine (8032-32-4))
• 沸点：
  521.1±53.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  马尿酸 、 trans-2-[p-formylstyryl]benzimidazole 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 以52%的产率得到(4Z)-4-(4-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)benzylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Two-photon absorption properties of push–pull oxazolones derivatives

  摘要：

  New fluorescent oxazolone derivatives with high two-photon absorption cross-section were synthesized. Electron donor (phenyl, dimethylaniline and furanyl) and acceptor (nitrobenzene and ethenyl-phenyl-benzimidazol) groups have been appended to the methylene end of 4-(methylidene)-2-phenyl-1,3-oxazol-5(4H)-one in order to produce an highly conjugated pi-system with push pull geometry. The linear and nonlinear optical properties of the oxazolones have been determined. The compounds with a high charge transfer from the substituent group to the oxazolone ring have relatively high two-photon absorption cross-sections (80-100 GM). The best performing nonlinear fluorophore being the benzimidazol derivative with a two-photon absorption cross-section of 80 GM and a relatively high emission quantum yield, phi = 0.31. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.005
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 对苯二甲醛 在 乙酸酐 、 溶剂黄146 作用下， 生成 trans-2-[p-formylstyryl]benzimidazole
  参考文献：
  名称：

  具有蓝/蓝双光子激发荧光的新型1 H-咪唑并[4,5- f ] [1,10]菲咯啉衍生物的绿色合成和光物理性质

  摘要：

  已开发出一种简单，快速且高效的方法来合成一系列新型的1 H-咪唑并[4,5- f ] [1,10]菲咯啉衍生物（1BN，2Py，3BI，4BT和5MOBI）通过无溶剂条件下的三组分一锅法反应。其结构的特征在于FT-IR，1 H NMR，1313 C NMR，MS和元素分析。在各种溶剂中系统地研究了它们的光物理性质，包括线性吸收，单光子激发荧光，双光子吸收和双光子激发荧光。结果表明，所有化合物均发出相对较强的蓝/青色荧光。1BN和5MOBI在THF中显示出较大的双光子吸收截面（471和654 GM）。此外，使用密度泛函理论研究了电子结构与光物理性质之间的关系。

  DOI：

  10.1016/j.tet.2017.03.075

文献信息

• Novel heterocycle-based organic molecules with two-photon induced blue fluorescent emission
  作者：Zhen-Li Huang、Hong Lei、Na Li、Zhi-Ren Qiu、He-Zhou Wang、Jing-Dong Guo、Yi Luo、Zeng-Pei Zhong、Xu-Feng Liu、Zhi-Hong Zhou

  DOI：10.1039/b300924f

  日期：2003.3.19

  Two-photon absorption and two-photon induced blue emission characteristics of a series of heterocycle-based organic molecules are investigated experimentally and by quantum-chemical computations. The molecules consist of a typical A–π–A′ structure, where heterocycle, styryl and formyl groups are employed as A, π-conjugated and A′ moieties, respectively. Experimental results indicate that significant enhancements in the blue emission efficiency and two-photon absorption cross-sections can be achieved by replacing S and O atoms with an N atom in the heterocycle acceptor moiety, which is also supported by the quantum-chemical computations. Additionally, larger two-photon absorption cross-sections can be obtained by choosing appropriate solvents, as indicated by the computations.

  通过实验和量子化学计算研究了一系列杂环基有机分子的双光子吸收和双光子诱导蓝光发射特性。这些分子具有典型的A–π–A′结构，其中杂环、苯乙烯和醛基分别作为A、π共轭和A′部分。实验结果表明，通过在杂环受体部分将硫和氧原子替换为氮原子，可以显著提高蓝光发射效率和双光子吸收截面，这一发现也得到了量子化学计算的支持。此外，计算结果表明，选择合适的溶剂可以获得更大的双光子吸收截面。
• Novel styrylbenzimidazolium-based fluorescent probe for reactive sulfur species: Selectively distinguishing between bisulfite and thiol amino acids
  作者：Jolanta Kolińska、Aleksandra Grzelakowska

  DOI：10.1016/j.saa.2021.120151

  日期：2021.12

  new fluorescent probe containing dicyanovinyl moiety has been designed and synthesized. Fluorescent probe based on styrylbenzimidazolium derivative was reported for the effective detection of bisulfite and distinguish it from biothiols by exploiting dicyanovinyl group as the recognition site. The photophysical properties of the novel styrylbenzimidazolium derivative were assessed by determination of

  在这项研究中，设计并合成了一种含有双氰基乙烯基部分的新型荧光探针。据报道，基于苯乙烯基苯并咪唑鎓衍生物的荧光探针可有效检测亚硫酸氢盐，并通过利用双氰基乙烯基作为识别位点将其与生物硫醇区分开来。通过测定吸收和荧光光谱、荧光量子产率和荧光寿命来评估新型苯乙烯基苯并咪唑鎓衍生物的光物理性质。已在 pH 值为 7.4 的水性介质中评估了其对各种分析物的光谱行为。化合物5荧光强度增幅最大在不同分析物存在的情况下观察到亚硫酸氢钠，检测限估计为 0.25 μM。使用荧光法将苯乙烯基苯并咪唑鎓染料用于检测各种葡萄酒样品中的亚硫酸氢盐。最后，评估了这种新型探针检测红酒样品中HSO 3 -的能力。
• A-π-A’化合物及其制备方法与应用
  申请人：浙江工业大学

  公开号：CN106946884B

  公开（公告）日：2019-02-01

  本发明公开了A‑π‑A'化合物及其制备方法与应用，所述A‑π‑A'化合物的结构如式(Ⅰ)或式(Ⅱ)所示，式(Ⅰ)和式(Ⅱ)化合物的化学名称分别为2‑[(1E)‑2‑[4‑(1H‑咪唑并[4,5‑f][1,10]菲咯啉‑2‑基)苯基]乙烯基]‑1H‑苯并咪唑和4‑[(1E)‑2‑[4‑(1H‑咪唑并[4,5‑f][1,10]菲咯啉‑2‑基)苯基]乙烯基]吡啶。本发明所述的A‑π‑A'化合物具有双光子吸收性能和双光子蓝色荧光性能，故进一步提供了式(Ⅰ)和式(Ⅱ)所示的A‑π‑A'化合物作为双光子吸收和双光子蓝色荧光材料的应用。
• A Novel Fluorescent Calix[4]arene Derivative with Benzimidazole Units For Selective Recognition to Fe and Cr
  作者：He Wang、Ya Feng、Jin Xue

  DOI：10.2174/157017809788681329

  日期：2009.7.1

  A novel fluorescent calix[4]arene derivative(1) with benzimidazole units as fluorophores and imino groups as ionophores at the upper rim has been synthesized in the cone conformation. Compound (1) was fully characterized by 1HNMR, 13C-NMR, IR and MS. The changes of UV-Vis spectra and fluorescent spectra upon metal ions complexation show compound (1) can selectively recognize Fe3+ and Cr3+ ions. The complexation ratio of compound (1) and Fe3+ or Cr3+ is 1:1. The association constant of compound (1) for Fe3+ was 3.4x104 and for Cr3+ was 2.8x105.

  合成了一种新型的荧光calix[4]arene衍生物（1），其上缘具有苯并咪唑单元作为荧光团和亚胺基团作为离子载体，呈锥形构象。化合物（1）通过1HNMR、13C-NMR、红外光谱和质谱进行了全面表征。金属离子络合时UV-Vis光谱和荧光光谱的变化表明，化合物（1）可以选择性地识别Fe3+和Cr3+离子。化合物（1）与Fe3+或Cr3+的络合比为1:1。化合物（1）对Fe3+的结合常数为3.4x10^4，对Cr3+的结合常数为2.8x10^5。
• Synthesis, Structures, and Two-Photon Absorption Properties of Two New Heterocycle-Based Organic Chromophores
  作者：Yun-Xing Yan、Hai-Hua Fan、Chi-Keung Lam、Hong Huang、Jing Wang、Sheng Hu、He-Zhou Wang、Xiao-Ming Chen

  DOI：10.1246/bcsj.79.1614

  日期：2006.10

  Two new heterocycle-based two-photon absorption chromophores, 4-[4-(4,5-diphenyl-1H-imidazol-2-yl)styryl]pyridine (2) and (E)-4-[2-(1H-benzimidazol-2-yl)vinyl]styryl}-N-methylpyridinium iodide (4), have been synthesized and characterized. The two molecules possess A–π–A′ structures. A π-deficient heteroaromatic ring (benzimidazole, 4,5-diphenyl-1H-imidazole) is used as an acceptor (A), and a pyridine ring is used as another acceptor (A′). One-photon-excited fluorescence, one-photon-fluorescence quantum yields, two-photon-excited fluorescence, and two-photon absorption cross-sections were investigated. Pumped with 740 and 800 nm laser excitation, compounds 2 and 4 had two-photon absorption cross-sections (41 and 38 GM) and two-photon-excited fluorescence (511 and 601 nm) in DMF, respectively. The crystal structure of compound 4 was determined by using X-ray single-crystal diffraction analysis.

  合成并表征了两种新的基于杂环的双光子吸收发色团，分别为4-[4-(4,5-二苯基-1H-咪唑-2-基)烯基]吡啶(2)和(E)-4-[2-(1H-苯并咪唑-2-基)乙烯基]烯基}-N-甲基吡啶钠碘化物(4)。这两种分子均具有A–π–A′结构。一个π缺乏的杂芳环（苯并咪唑、4,5-二苯基-1H-咪唑）被用作受体（A），而吡啶环则作为另一个受体（A′）。研究了单光子激发荧光、单光子荧光量子产率、双光子激发荧光和双光子吸收截面。在740和800 nm激光激发下，化合物2和4在DMF中的双光子吸收截面分别为41和38 GM，双光子激发荧光波长为511和601 nm。化合物4的晶体结构通过X射线单晶衍射分析确定。