4,4-二氟-8-（4'-碘苯基）-1,7-双-（1'-萘基）-4-硼烷-3α，4α-二氮杂-s-茚并四烯 | 216255-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4,4-二氟-8-（4'-碘苯基）-1,7-双-（1'-萘基）-4-硼烷-3α，4α-二氮杂-s-茚并四烯
• 英文名称: 4,4-difluoro-8-(4'-iodophenyl)-1,7-bis(1'-naphthyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-Difluoro-8-(4'-iodophenyl)-1,7-bis-(1'-napthyl)-4-bora-3alpha,4alpha-diaza-s-indacene；2,2-difluoro-8-(4-iodophenyl)-4,12-dinaphthalen-1-yl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 216255-54-8
• 化学式: C₃₅H₂₂BF₂IN₂
• 分子量: 646.285
• InChiKey: SDJXSBQAERLUKD-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166°C

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  8.0
• 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

• 作为产物：
  描述：

  N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole 在 三氟化硼乙醚 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 31.33h， 生成 4,4-二氟-8-（4'-碘苯基）-1,7-双-（1'-萘基）-4-硼烷-3α，4α-二氮杂-s-茚并四烯
  参考文献：
  名称：

  3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes:  Synthesis, Spectroscopic, Electrochemical, and Structural Properties

  摘要：

  This research was undertaken to obtain new "BODIPY" dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert-butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl-substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.

  DOI：

  10.1021/jo990796o

文献信息

• 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes:  Synthesis, Spectroscopic, Electrochemical, and Structural Properties
  作者：Armin Burghart、Heejin Kim、Mike B. Welch、Lars H. Thoresen、Joe Reibenspies、Kevin Burgess、Fredrik Bergström、Lennart B.-Å. Johansson

  DOI：10.1021/jo990796o

  日期：1999.10.1

  This research was undertaken to obtain new "BODIPY" dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert-butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl-substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.