meso-(5-bromothiophen-2-yl)dipyrromethane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: meso-(5-bromothiophen-2-yl)dipyrromethane
• 英文别名: 2,2 inverted exclamation mark-[(5-Bromothiophen-2-yl)methylene]bis(1H-pyrrole)；2-[(5-bromothiophen-2-yl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• 化学式: C₁₃H₁₁BrN₂S
• 分子量: 307.214
• InChiKey: IYEMESXJBWMNBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  meso-(5-bromothiophen-2-yl)dipyrromethane 在 N-溴代丁二酰亚胺(NBS) 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,5-dibromo-8-(5’-bromothiophen-2’-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  溴化 BODIPY 晶体中的卤素键：晶体学和计算研究

  摘要：

  随着溴原子数量的增加，分析了 BODIPY 中的分子间相互作用，特别是卤素键 (XB)。发现了单配位和分叉的卤素键，并通过 XB 相互作用形成了菱形结构。计算分析和指纹图表明，Br⋅⋅⋅Br 接触贡献的增加取决于溴原子的数量。

  DOI：

  10.1002/chem.202302847
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 吡咯 在 iodine loaded amine functionalized metal organic framework 作用下， 以56%的产率得到meso-(5-bromothiophen-2-yl)dipyrromethane
  参考文献：
  名称：

  MOF as a syringe pump for the controlled release of iodine catalyst in the synthesis of meso-thienyl dipyrromethanes

  摘要：

  一种富含碘的NH₂-MOF作为一种注射泵，用于在噻吩二吡咯甲烷合成中缓慢释放碘催化剂。

  DOI：

  10.1039/c5cc06311f

文献信息

• On the structure of meso-substituted F-BODIPYs and their assembly in molecular crystals: An experimental-theoretical approach
  作者：Elba Xochitiotzi-Flores、Alisul A. Islas-Mejía、Héctor García-Ortega、Margarita Romero-Ávila、José Manuel Mendez-Stivalet、María del Pilar Carreón-Castro、Rosa Santillan、Mauricio Maldonado-Domínguez、Rafael Arcos-Ramos、Norberto Farfán

  DOI：10.1016/j.jorganchem.2016.01.021

  日期：2016.3

  structurally analogous, yet their crystal packing motifs displayed remarkable differences due to contrasting hydrogen-bonding interactions. A CASTEP study of the unit cell for each compound provided the theoretical band structure and density-of-states (DOS) diagrams for each molecular crystal, suggesting a semiconductor character for both solids. Analysis of the computed electron density with Bader's

  的分子晶体内消旋- （5 - （（4-甲酰基苯基）乙炔基）噻吩-2-基）-4,4-二氟-4-硼-3a，4a-二氮杂-小号-indacene图4a和内消旋- （4-（ （4-甲酰基苯基）乙炔基）苯基）-4,4-二氟-4-硼-3a，4a-二氮杂-小号-indacene 4b中使用钯合成（0）催化的Sonogashira交叉偶联反应和使用，其特征在于试验-理论方法。F-BODIPYs 4a-b的晶体结构在结构上类似，但由于氢键相互作用的对比，它们的晶体堆积图案显示出显着差异。对每种化合物的晶胞进行的CASTEP研究提供了每种分子晶体的理论能带结构和状态密度（DOS）图，表明两种固体的半导体特性。使用Bader的QTAIM对计算的电子密度的分析描述了每个周期系统内的分子间接触网络，而自然键合轨道（NBO）显示出堆叠单元之间的同相重叠，表示通过堆叠使电子密度发生了分子间离域化。TDDFT分析溶液的U
• Optical properties of two fluorene derived BODIPY molecular rotors as fluorescent ratiometric viscosity probes
  作者：Elba Xochitiotzi-Flores、Arturo Jiménez-Sánchez、Héctor García-Ortega、Nuria Sánchez-Puig、Margarita Romero-Ávila、Rosa Santillan、Norberto Farfán

  DOI：10.1039/c5nj03339j

  日期：——

  Two fluorescent ratiometric fluorene derived BODIPY probes present a sensitive response to microviscosity changes.

  两种荧光比色法衍生的BODIPY探针对微粘度变化呈现敏感响应。
• BODIPY-Ethynylestradiol molecular rotors as fluorescent viscosity probes in endoplasmic reticulum
  作者：Diego Martínez-Bourget、Erika Rocha、Pablo Labra-Vázquez、Rosa Santillan、Benjamín Ortiz-López、Vianney Ortiz-Navarrete、Valérie Maraval、Remi Chauvin、Norberto Farfán

  DOI：10.1016/j.saa.2022.121704

  日期：2022.12

  capability for sensing changes in viscosity, fluorescent molecular rotors (FMRs) have emerged as potential tools to develop several promising viscosity probes; most of them, however, localize non-selectively within cells, precluding changes in the viscosity of specific cellular microdomains to be studied by these means. Following previous reports on enhanced fluorophore uptake efficiency and selectivity

  由于能够感知粘度变化，荧光分子转子 (FMR) 已成为开发几种有前途的粘度探针的潜在工具。然而，它们中的大多数在细胞内非选择性定位，从而排除了通过这些方法研究的特定细胞微域的粘度变化。继先前关于通过掺入生物亚分子片段提高荧光团吸收效率和选择性的报道之后，我们在此报告了两种基于乙炔雌二醇纺锤体的潜在 BODIPY FMR，这是一种被人类细胞很好识别的非细胞毒性半合成雌激素。对这些荧光团用作 FMR 的潜力进行了批判性评估，包括探针的光物理表征、SXRD 研究和 TD-DFT 计算，
• Brominated BODIPYs as potential photosensitizers for photodynamic therapy using a low irradiance excitation
  作者：Valdez-Calderón Alejandro、Farfán-Paredes Mónica、Araujo-Padilla Xelha、Rodríguez Mario、Ramos-Ortiz Gabriel、Farfán Norberto、Ramón-Gallegos Eva

  DOI：10.1016/j.poly.2019.114207

  日期：2020.1

  Three novel BODIPY-chromophores 4, 6 and 7 were synthesized by simple condensation reaction of thiocarboxaldehyde and pyrrole ring. Molecular structures were designed to contain thiophene rings and different arrangements for bromine substitution. The effect of these arrangements on the generation of singlet oxygen and optical properties was studied. In general, the presence of thiophene rings produces red-shifts in absorption spectra while three bromine substitution (6) tend to produce the largest singlet oxygen generation. Results show that these BODIPYs are excellent chromophores with high absorption coefficient, however they are poor fluorophores (with quantum yields <1%). Compounds 4, 6 and 7 were evaluated in three different organic solvents for the generation of singlet oxygen by using a spectrophotometric method, obtaining maximum quantum efficiencies of singlet oxygen generation of 84, 93 and 74% for 4, 6 and 7, respectively. The compounds comprise excellent photo- and chemical stability against reactive oxygen species. These BODIPYs show good compatibility to aqueous media and conserve most of their optical properties obtained in organic solvents. These results motivated to evaluate these BODIPYs as photosensitizers in photodynamic therapy (PDT). In particular, 4 used as photosensitizer showed 60% of HeLa cells viability reduction, determined by MIT assay. (C) 2019 Elsevier Ltd. All rights reserved.