3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-indacene
• 英文别名: 3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacence；10-(4-bromophenyl)-3,7-dichloro-5,5-difluoro-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide；3,5-dichloro-8-(4’-bromophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；8-(4-Bromophenyl)-4,12-dichloro-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 化学式: C₁₅H₈BBrCl₂F₂N₂
• 分子量: 415.86
• InChiKey: QNBYJUDRGLIDBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-indacene 在 氯磺酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以92%的产率得到sodium 2-sulfonate-3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  功能化的水溶性BODIPY衍生物的合成及光谱性质

  摘要：

  这项工作的目的是形成水溶性4,4-二氟-4-硼3a，4a-二氮杂s-茚并二烯（BODIPY）衍生物。为几种BODIPY染料开发了磺化条件，得到了单磺化产物1a - 3a和二磺化产物1b - 3b。用芳基碘化物将化合物1官能化以用于有机金属偶联。类似地，2具有芳族溴化物，但也具有两个可通过S N Ar反应取代的氯原子。胺3适合于通过酰化反应与生物分子偶联。重氮化/叠氮化物反应顺序用于转化胺3变成叠氮化物4 ; 后者可以通过点击反应功能化，如4b转化为5所示。化合物5被设计成具有酸官能团以促进活化和与胺偶联。这些材料的光谱数据表明它们是水性环境中的高荧光探针。

  DOI：

  10.1021/jo702463f
• 作为产物：
  描述：

  5-(4-bromophenyl)dipyrromethane 在 N-氯代丁二酰亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3,5-dichloro-8-(4'-bromophenyl)-4,4-difluoro-4-bora-3a,4a-indacene
  参考文献：
  名称：

  Versatile synthetic methods for the engineering of thiophene-substituted Bodipy dyes

  摘要：

  Novel thienyl-borondiazadipyrromethene (Bodipy) dyes have been prepared using boronic acids or boronate reagents as cross-coupling mediators. A key dichloro/bromo-Bodipy starting material appears to be a useful starting material for such coupling reactions, enabling the synthesis of various symmetrically and unsymmetrically substituted thienyl-dyes. An alternative means of introducing thienyl substituents is through Knoevenagel substitution in the 3 and 5 positions of Bodipy by reaction with a formyl-functionalized thiophene derivative, resulting in systems of extended delocalization. All these Bodipy derivatives are stable and exhibit pronounced fluorescence on irradiation in the S-0 -> S-1 transition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.163

文献信息

• 3- and 5-Functionalized BODIPYs via the Liebeskind-Srogl reaction
  作者：Junyan Han、Oswaldo Gonzalez、Angelica Aguilar-Aguilar、Eduardo Peña-Cabrera、Kevin Burgess

  DOI：10.1039/b818390b

  日期：——

  Chemoselective cross-coupling reactions were demonstrated for C–S bonds in the BODIPY dyes 1 and 4, and similar reactions were applied to make the two-dye cassette system 11.

  展现了用于BODIPY染料1和4中C–S键的化学选择性交叉耦合反应，类似反应也应用于制备双染料盒系统11。
• Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core
  作者：Lingling Li、Binh Nguyen、Kevin Burgess

  DOI：10.1016/j.bmcl.2007.10.103

  日期：2008.5

  systems 1 and 2 were prepared and then used as substrates to explore S(N)Ar and F-B displacement reactions. Chloride was easily displaced from 1 by a piperidine/ester, methylmagnesium bromide selectively displaced fluoride, and cyanide could attack both sites. System 2 readily added soft nucleophiles to the electrophilic carbon atoms, providing a new method for bioconjugation of BODIPYs to proteins while

  制备了新的 BODIPY 系统 1 和 2，然后用作底物来探索 S(N)Ar 和 FB 置换反应。氯化物很容易被哌啶/酯从 1 置换，甲基溴化镁选择性置换氟化物，氰化物可以攻击两个位点。系统 2 很容易将软亲核试剂添加到亲电碳原子中，为 BODIPY 与蛋白质的生物偶联提供了一种新方法，同时还引入了 (19)F 探针。
• Carborane‐BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling
  作者：Chiara Bellomo、Mahdi Chaari、Justo Cabrera‐González、Marco Blangetti、Chiara Lombardi、Annamaria Deagostino、Clara Viñas、Nerea Gaztelumendi、Carme Nogués、Rosario Nuñez、Cristina Prandi

  DOI：10.1002/chem.201802901

  日期：2018.10.17

  library of carborane‐BODIPY/aza‐BODIPY dyads were efficiently synthesized by means of a novel convergent synthetic approach, the key step of which is a Pd‐catalyzed Heck coupling reaction. The structural characterization and photoluminescence properties of the newly synthesized dyads were evaluated. The presence of the carborane did not significantly alter the photophysical patterns of the BODIPY or aza‐BODIPY

  通过新颖的聚合合成方法有效合成了一个小分子的碳硼烷-BODIPY /氮杂-BODIPY二元组，其关键步骤是钯催化的Heck偶联反应。评价了新合成的二元组的结构表征和光致发光性质。碳硼烷的存在不会显着改变最终荧光团中BODIPY或aza-BODIPY的光物理模式，但会导致发射荧光量子产率的降低，范围从aza-BODIPY的1.4％降至48％适用于BODIPY二元组。碳硼烷-BODIPY成对成功掺入细胞，尤其是化合物2，4和13，说明其胞质定位。荧光和生物相容性特性使这些化合物成为体外细胞追踪的理想候选者。
• Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores
  作者：Clara Orofino-Pena、Diego Cortizo-Lacalle、Joseph Cameron、Muhammad T Sajjad、Pavlos P Manousiadis、Neil J Findlay、Alexander L Kanibolotsky、Dimali Amarasinghe、Peter J Skabara、Tell Tuttle、Graham A Turnbull、Ifor D W Samuel

  DOI：10.3762/bjoc.10.285

  日期：——

  Star-shaped conjugated systems with varying oligofluorene arm length and substitution patterns of the central BODIPY core have been synthesised, leading to two families of compounds, T-B1–T-B4 and Y-B1–Y-B4, with T- and Y-shaped motifs, respectively. Thermal stability, cyclic voltammetry, absorption and photoluminescence spectroscopy of each member of these two families were studied in order to determine their suitability as emissive materials in photonic applications.

  具有不同寡聚芴臂长和中心BODIPY核替代模式的星形共轭体系已被合成，导致两个化合物家族，分别为T-和Y形图案的T-B1-T-B4和Y-B1-Y-B4。研究了这两个家族的每个成员的热稳定性、循环伏安法、吸收和光致发光光谱，以确定它们作为光子应用中发射材料的适用性。
• Quasi‐One‐Dimensional Electronic Systems Formed from Boron Dipyrromethene (BODIPY) Dyes
  作者：Raymond Ziessel、Sandra Rihn、Anthony Harriman

  DOI：10.1002/chem.201001142

  日期：2010.10.18

  spectral range and emit in the far‐red region in almost quantitative yield. A notable exception to this generic behaviour is provided by the anthracenyl derivative, which exhibits charge‐transfer absorption and emission spectra in weakly polar media at ambient temperature. Regular BODIPY‐like behaviour is restored in a glassy matrix at 77 K. Overall, these new dyes represent an important addition to the range

  已经设计出合成策略，以允许合理设计和分离可吸收大部分可见区域的高度着色的硼二吡咯亚甲基（BODIPY）染料。每种染料都有一个芳基多环（通常是pyr或per），它们通过3,5位上的共轭系链连接到BODIPY中央核。单官能化和双官能化的衍生物均可使用，在某些情况下同时含有containing和per残基。对于所有新化合物，已在环境温度下的溶液中以及在77 K的玻璃状基质中记录了光物理性质。芳基多环的存在会影响BODIPY原子核的吸收和发射最大值，因此证实了这些单元以电子方式耦合。的确，带的最大值和振动子强度取决于整个分子的共轭长度，而没有多环荧光的迹象。结果，辐射速率常数趋于随每个附加的附属物而增加。连接的性质（苯乙烯基，乙烯基或乙炔基）也影响光物理性质，特别是吸收光谱在芳基多环的区域中受到干扰。含per的BODIPY衍生物在很宽的光谱范围内吸收，并以几乎定量的产率发射到远红色区域。蒽基衍生物