spiro[[8H]indeno[2,1-b]thiophene-8,9'-fluorene] | 884499-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro[[8H]indeno[2,1-b]thiophene-8,9'-fluorene]
• 英文别名: Spiro[fluorene-9,4'-indeno[2,1-b]thiophene]；spiro[fluorene-9,4'-indeno[2,1-b]thiophene]
• CAS: 884499-24-5
• 化学式: C₂₃H₁₄S
• 分子量: 322.43
• InChiKey: IDIWTYBVYVFUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  spiro[[8H]indeno[2,1-b]thiophene-8,9'-fluorene] 、 9-(3-phenylthiophen-2-yl)fluoren-9-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到2'-(9-(4-phenylthiophen-2-yl)fluoren-9-yl)spiro[fluorene-9,8'-indeno[2,1-b]thiophene]
  参考文献：
  名称：

  Diarylfluorenes-based π-stacked molecules: synthesis, X-ray crystallography, and supramolecular light-emitting devices

  摘要：

  A series of intramolecular pi-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF3 center dot Et2O-mediated Friedel Crafts reaction of carbinols. Their intramolecular pi-pi stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m(2), a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The pi-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.02.090
• 作为产物：
  描述：

  3-苯基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 spiro[[8H]indeno[2,1-b]thiophene-8,9'-fluorene]
  参考文献：
  名称：

  新型螺旋[[8 H ]茚并[ 2,1- b ]-噻吩-8,9'-芴]构件的高效合成

  摘要：

  我们已经开发出有效的合成途径，以获得新型的建筑材料螺[[8 H ]茚并[ 2,1- b ]噻吩-8,9'-芴]（SITF），含一噻吩的螺二芴类似物，并构建了蓝光。发射材料，包括2'，7'-双（[[1,1'-联苯] -4-基）-螺[茚并[ 2,1- b ]噻吩-8,9'-芴]（BBP–SITF ）和2'，7'-双（9,9'-spirobifluoren -2-yl）spiro [[8 H ] indeno [2,1- b ]-噻吩-8,9'-芴]（BSBF–SITF） 。BSBF-SITF已证明是一种稳定的蓝色发光材料，具有高PL量子效率（89％）和在噻吩的C2处具有独特的区域选择性特征，这表明BSBF-SITF可用于构建复杂的光电系统。

  DOI：

  10.1016/j.tetlet.2006.06.143

文献信息

• Facile Synthesis of Complicated 9,9-Diarylfluorenes Based on BF₃·Et₂O-Mediated Friedel−Crafts Reaction
  作者：Ling-Hai Xie、Xiao-Ya Hou、Yu-Ran Hua、Chao Tang、Feng Liu、Qu-Li Fan、Wei Huang

  DOI：10.1021/ol061268j

  日期：2006.8.1

  (BF3OEt2)-O-.-mediated Friedel-Crafts reaction of 9-phenyl-fluoren-9-ol with electron-rich aromatic substrates to prepare a new family of complicated 9,9-diarylfluorenes is described. The 9,9-diarylfluorenes tethered with various functional substituents, e.g., bulky spiro units, hole-transporting moieties, and fluorescent dyes, will be promising building blocks for the construction of optoelectronic materials.

  文中描述了以 (BF3OEt2)-O- 为介导剂，通过 Friedel-Crafts 反应将 9-苯基芴-9-醇与电子丰富的芳香底物反应，制备出一类结构复杂的 9,9-二芳基芴。这些 9,9-二芳基芴带有多种功能取代基，例如大位阻的螺环结构、空穴传输基团和荧光染料，有望成为构建光电材料的理想构建模块。
• An efficient synthesis of novel spiro[[8H]indeno[2,1-b]-thiophene-8,9′-fluorene] building block for blue light-emitting materials
  作者：Ling-Hai Xie、Ting Fu、Xiao-Ya Hou、Chao Tang、Yu-Ran Hua、Rui-Jie Wang、Qu-Li Fan、Bo Peng、Wei Wei、Wei Huang

  DOI：10.1016/j.tetlet.2006.06.143

  日期：2006.9

  obtain a novel building block spiro[[8H]indeno[2,1-b]thiophene-8,9′-fluorene] (SITF), a monothiophene-containing spirobifluorene analogue, and constructed blue light-emitting materials, including 2′,7′-bis([1,1′-biphenyl]-4-yl)-spiro[indeno[2,1-b]thiophene-8,9′-fluorene] (BBP–SITF) and 2′,7′-bis(9,9′-spirobifluoren-2-yl)spiro[[8H]indeno[2,1-b]-thiophene-8,9′-fluorene] (BSBF–SITF). BSBF–SITF has shown

  我们已经开发出有效的合成途径，以获得新型的建筑材料螺[[8 H ]茚并[ 2,1- b ]噻吩-8,9'-芴]（SITF），含一噻吩的螺二芴类似物，并构建了蓝光。发射材料，包括2'，7'-双（[[1,1'-联苯] -4-基）-螺[茚并[ 2,1- b ]噻吩-8,9'-芴]（BBP–SITF ）和2'，7'-双（9,9'-spirobifluoren -2-yl）spiro [[8 H ] indeno [2,1- b ]-噻吩-8,9'-芴]（BSBF–SITF） 。BSBF-SITF已证明是一种稳定的蓝色发光材料，具有高PL量子效率（89％）和在噻吩的C2处具有独特的区域选择性特征，这表明BSBF-SITF可用于构建复杂的光电系统。
• Diarylfluorenes-based π-stacked molecules: synthesis, X-ray crystallography, and supramolecular light-emitting devices
  作者：Yang Yang、Jian-Feng Zhao、Ran-Ran Liu、Jie-Wei Li、Ming-Dong Yi、Guo-Hua Xie、Ling-Hai Xie、Yong-Zheng Chang、Cheng-Rong Yin、Xin-Hui Zhou、Yi Zhao、Yan Qian、Wei Huang

  DOI：10.1016/j.tet.2013.02.090

  日期：2013.7

  A series of intramolecular pi-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF3 center dot Et2O-mediated Friedel Crafts reaction of carbinols. Their intramolecular pi-pi stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m(2), a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The pi-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics. (C) 2013 Published by Elsevier Ltd.