| 1013425-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• CAS: 1013425-08-5
• 化学式: C₃₆H₃₄N₄S₂
• 分子量: 586.825
• InChiKey: IITRLCTZJBGUHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.51
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.64
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  、 碘甲烷 以 乙腈 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  Modular Fluorescent Benzobis(imidazolium) Salts:  Syntheses, Photophysical Analyses, and Applications

  摘要：

  A series of benzobis(imidazolium) (BBI) salts has been prepared and studied as a new class of versatile fluorescent materials. Using a high yielding, modular synthetic strategy, 13131 salts with a range of functionality poised for investigating fundamental and applications-oriented characteristics, including emission wavelength tunability, solvatochromism, red-edge excitation, chemical stability, multiphoton excitation, and protein conjugation, were prepared in overall yields of 40-97%. Through structural variation, the BBIs exhibited lambda(em) ranging between 329 and 561 nm while displaying Phi(f)s up to 0.91. In addition, the emission characteristics of these salts were found to exhibit strong solvent dependencies with Stokes shifts ranging from 4570 to 13 793 cm(-1), depending on the nature of the BBI core. Although red-edge effects for BBI salts with Br and BF4 counterions were found to be similar, unique characteristics were displayed by an analogue with MeSO4 anions. The stability of an amphiphilic BBI was quantified in aqueous solutions of varying pH, and > 85% of the emission intensity was retained after 2 h at pH 3-9. Through multiphoton excitation experiments in aqueous solutions, a BBI salt was found to exhibit three-photon fluorescence action cross sections similar to serotonin. The application of BBI salts as fluorescent protein tags was demonstrated by conjugating bovine serum albumin to a maleimide-functionalized derivative.

  DOI：

  10.1021/ja7102247
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 在 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以78%的产率得到
  参考文献：
  名称：

  Modular Fluorescent Benzobis(imidazolium) Salts:  Syntheses, Photophysical Analyses, and Applications

  摘要：

  A series of benzobis(imidazolium) (BBI) salts has been prepared and studied as a new class of versatile fluorescent materials. Using a high yielding, modular synthetic strategy, 13131 salts with a range of functionality poised for investigating fundamental and applications-oriented characteristics, including emission wavelength tunability, solvatochromism, red-edge excitation, chemical stability, multiphoton excitation, and protein conjugation, were prepared in overall yields of 40-97%. Through structural variation, the BBIs exhibited lambda(em) ranging between 329 and 561 nm while displaying Phi(f)s up to 0.91. In addition, the emission characteristics of these salts were found to exhibit strong solvent dependencies with Stokes shifts ranging from 4570 to 13 793 cm(-1), depending on the nature of the BBI core. Although red-edge effects for BBI salts with Br and BF4 counterions were found to be similar, unique characteristics were displayed by an analogue with MeSO4 anions. The stability of an amphiphilic BBI was quantified in aqueous solutions of varying pH, and > 85% of the emission intensity was retained after 2 h at pH 3-9. Through multiphoton excitation experiments in aqueous solutions, a BBI salt was found to exhibit three-photon fluorescence action cross sections similar to serotonin. The application of BBI salts as fluorescent protein tags was demonstrated by conjugating bovine serum albumin to a maleimide-functionalized derivative.

  DOI：

  10.1021/ja7102247