2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide | 500772-34-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide
• 英文别名: 2-bromo-3,5-dimethyldithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide；4-Bromo-5,9-dimethyl-3,7lambda6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide；4-bromo-5,9-dimethyl-3,7λ6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide
• CAS: 500772-34-9
• 化学式: C₁₀H₇BrO₂S₃
• 分子量: 335.266
• InChiKey: CTJYWZWXBYFVOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide 在 tetrakis(triphenylarsine)palladium(0) N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 5.0h， 生成 2-phenyl-3,5-dimethyl-6-[(4-dimethyl(chloromethyl)silyl)phenyl]dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
  参考文献：
  名称：

  Rigid-Core Fluorescent Oligothiophene-S,S-dioxide Isothiocyanates. Synthesis, Optical Characterization, and Conjugation to Monoclonal Antibodies

  摘要：

  In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.

  DOI：

  10.1021/jo026298o
• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 双(三丁基锡)硫醚 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 25.0h， 生成 2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide
  参考文献：
  名称：

  噻吩，二噻吩并噻吩S，S-二氧化物，噻吩并[3,4]吡嗪和2,1,3-苯并噻二唑的混合低聚物的设计与合成：机械敏感系统的翻转筛选。

  摘要：

  具有大表面积和高量子产率的单体，即荧光鳍状肢，已被工程化为扭曲的推挽式低聚物，以产生具有高机械敏感性和长荧光寿命的膜探针。在这里，与原始的二噻吩并噻吩S，S-二氧化物相比，描述了噻吩并[3,4]吡嗪和2,1,3-苯并噻二唑的合成和表征。迄今为止，二硫代噻吩S，S-二氧化锡脚蹼已被证实是最好的报道，而单个脚蹼探针的结果较差则表明需要两个脚蹼才能使探针真正“游动”，即具有较高的机械敏感性。

  DOI：

  10.1002/open.201402139

文献信息

• Fluorescent Flippers for Mechanosensitive Membrane Probes
  作者：Marta Dal Molin、Quentin Verolet、Adai Colom、Romain Letrun、Emmanuel Derivery、Marcos Gonzalez-Gaitan、Eric Vauthey、Aurélien Roux、Naomi Sakai、Stefan Matile

  DOI：10.1021/ja5107018

  日期：2015.1.21

  In this report, fluorescent flippers are introduced to create planarizable pushpull probes with the mechanosensitivity and fluorescence lifetime needed for practical use in biology. Twisted pushpull scaffolds with large and bright dithienothiophenes and their S,S-dioxides as the first fluorescent flippers are shown to report on the lateral organization of lipid bilayers with quantum yields above 80% and lifetimes above 4 ns. Their planarization in liquid-ordered (Lo) and solid-ordered (So) membranes results in red shifts in excitation of up to +80 nm that can be transcribed into red shifts in emission of up to +140 nm by Forster resonance energy transfer (FRET). These unique properties are compatible with multidomain imaging in giant unilamellar vesicles (GUVs) and cells by confocal laser scanning or fluorescence lifetime imaging microscopy. Controls indicate that strong push-pull macrodipoles are important, operational probes do not relocate in response to lateral membrane reorganization, and two flippers are indeed needed to really swim, i.e., achieve high mechanosensitivity.
• Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils
  作者：Ilaria Palamà、Francesca Di Maria、Ilenia Viola、Eduardo Fabiano、Giuseppe Gigli、Cristian Bettini、Giovanna Barbarella

  DOI：10.1021/ja2065522

  日期：2011.11.9

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.
• Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene <i>S</i> ,<i>S</i> -Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems
  作者：Quentin Verolet、Saeideh Soleimanpour、Kaori Fujisawa、Marta Dal Molin、Naomi Sakai、Stefan Matile

  DOI：10.1002/open.201402139

  日期：2015.6

  push–pull oligomers to create membrane probes with high mechanosensitivity and long fluorescence lifetime. Here, the synthesis and characterization of thieno[3,4]pyrazines and 2,1,3‐benzothiadiazoles are described in comparison with the original dithienothiophene S,S‐dioxides. Dithienothiophene S,S‐dioxide flippers are confirmed as the best reported so far, and poor results with single flipper probes support

  具有大表面积和高量子产率的单体，即荧光鳍状肢，已被工程化为扭曲的推挽式低聚物，以产生具有高机械敏感性和长荧光寿命的膜探针。在这里，与原始的二噻吩并噻吩S，S-二氧化物相比，描述了噻吩并[3,4]吡嗪和2,1,3-苯并噻二唑的合成和表征。迄今为止，二硫代噻吩S，S-二氧化锡脚蹼已被证实是最好的报道，而单个脚蹼探针的结果较差则表明需要两个脚蹼才能使探针真正“游动”，即具有较高的机械敏感性。
• Rigid-Core Fluorescent Oligothiophene-<i>S</i>,<i>S</i>-dioxide Isothiocyanates. Synthesis, Optical Characterization, and Conjugation to Monoclonal Antibodies
  作者：Giovanna Sotgiu、Massimo Zambianchi、Giovanna Barbarella、Fabio Aruffo、Franco Cipriani、Alfredo Ventola

  DOI：10.1021/jo026298o

  日期：2003.2.1

  In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.