2,5-bis(9-hydroxyfluoren-9-yl)thieno<2,3-b>thiophene | 160059-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,5-bis(9-hydroxyfluoren-9-yl)thieno<2,3-b>thiophene
• 英文别名: 9-[5-(9-Hydroxyfluoren-9-yl)thieno[2,3-b]thiophen-2-yl]fluoren-9-ol；9-[5-(9-hydroxyfluoren-9-yl)thieno[2,3-b]thiophen-2-yl]fluoren-9-ol
• CAS: 160059-02-9
• 化学式: C₃₂H₂₀O₂S₂
• 分子量: 500.642
• InChiKey: JFXMNEQFIZHKHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 1,2,4,5-四氰基苯 、 2,5-bis(9-hydroxyfluoren-9-yl)thieno<2,3-b>thiophene 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Fluorescent Molecular Complexes of 9-Hydroxyfluoren-9-yl Substituted Thiophene and Thienothiophenes with 1,2,4,5-Tetracyanobenzene:Crystalline Complexation of Bulky and Conformationally Mobile Molecules

  摘要：

  Bis(9-hydroxyfluoren-9-yl)-substituted thiophene (1), thieno-[3,2-b]thiophene (2), and thieno[2,3-b]thiophene (3) were recrystallized with 1,2,4,5-tetracyanobenzene (TCNB) from CH2Cl2 to afford crystalline complexes (1)(2)(TCNB), (2)(TCNB)(CH2Cl2), and (3)(TCNB)(CH2Cl2), respectively. These crystals are yellow and fluorescent in the solid state. X-ray analyses of (1)(2)(TCNB) and (3)(TCNB)(CH2Cl2) revealed that the fluorenyl moieties and the TCNB ring are arranged in a face-to-face manner. The coloring and fluorescent properties are ascribed to a weak charge-transfer (CT) interaction, which is brought about by lattice controlled packing rather than intrinsic CT interactions. The nature of the fluorescence is discussed on the basis of the crystal structure and the lifetime of the emission.

  DOI：

  10.1080/10587259608039373
• 作为产物：
  描述：

  2,5-二溴噻吩[2,3-b]噻吩 、 9-芴酮 在 正丁基锂 作用下， 生成 2,5-bis(9-hydroxyfluoren-9-yl)thieno<2,3-b>thiophene
  参考文献：
  名称：

  Clathrate Formations with Isomeric Host Compounds Based on Thieno[3,2-b]thiophene and Thieno[2,3-b]thiophene: Inclusion Modes and Crystal Structures

  摘要：

  Two host compounds 1 and 2, which are composed of isomeric thieno[3,2-b]thiophene and thieno[2,2-b]thiophene, respectively, afforded crystalline host-guest inclusion complexes. Benzene and DMSO were chosen as guest species capable of the least and the most intense host-guest interactions, respectively, and the X-ray crystal structures of their clathrates were investigated. Benzene was enclathrated in each of 1 and 2 with different host-to-guest ratios to give (1)(3)(benzene)(4) and(a)(benzene). In both crystals, there are pairs of benzene molecules arranged in parallel offset. Crystal data: (1)(3)(benzene)(4), triclinic, P $($) over bar$$ 1, a = 13.940(5)Angstrom, b = 15.537(2)Angstrom, c = 13.040(4)Angstrom, alpha = 104.13(2)degrees, beta = 119.91(2)degrees, gamma = 92.24(2)degrees, V = 2330(1)Angstrom(3), Z = 1; (2)(benzene), triclinic, P $($) over bar$$ 1, a = 12.427(4)Angstrom, b = 13.041(4)Angstrom, c = 10.733(2)Angstrom, alpha = 92.97(2)degrees, beta = 104.79(2)degrees, gamma = 117.10(1)degrees, V = 1648.2(7)Angstrom(3), Z = 2. The(2)(benzene) crystals eliminate the guest at significantly high temperature, 128 degrees C, which is discussed in light of the hydrogen-bonded rigid host lattices. The crystals including DMSO, (1)(DMSO)(2), and (2)(DMSO)(2) were isomorphous. Crystal data: (1)(DMSO)(2), triclinic, P $($) over bar$$ 1, a = 12.618(1)Angstrom, b = 13.161(2)Angstrom, c = 11.615(3)Angstrom, alpha = 115.41(2)degrees, beta = 97.04(2)degrees, gamma = 103.41(1)degrees, V = 1639.7(6)Angstrom(3), Z = 2; (2)(DMSO)(2), triclinic, P $($) over bar$$ 1, a = 12.613(1)Angstrom, b = 13.383(3)Angstrom, c = 11.601(2)Angstrom, alpha = 115.49(1)degrees, beta = 97.28(1)degrees, gamma = 104.60(1)degrees, V = 1647.3(5)Angstrom(3), Z = 2. The formation of the isostructural crystals is discussed on the basis of the strong hydrogen bonding between the host and guest molecules, which counteracts the structural and electronic differences between 1 and 2. In line with this interpretation, the conformational preference of the OC-CS bonds due to the electrostatic O ... S attraction was overcome in the DMSO inclusion crystals. In spite of the isostructural crystal packing, their thermal behavior of guest release, as investigated by DSC measurements, is rather different; (1)(DMSO)(2) loses the guest DMSO molecules stepwise at 111 and 138 degrees C, whereas (2)(DMSO)(2) does at 96 and 159 degrees C.

  DOI：

  10.1021/jo00125a020

文献信息

• Solid-State Photosolvolysis of Clathrate Crystals Including Ethanol as a Guest Component
  作者：Naoto Hayashi、Yasuhiro Mazaki、Keiji Kobayashi

  DOI：10.1080/10587259408027166

  日期：1994.6

  A simple bimolecular photosubstitution at a saturated carbon atom of the host by the guest molecule has been observed in the clathrate crystals which are composed of 9-fluorenyl substituted thienothiophenes as a host component and include ethanol as a guest species. Based on the X-ray analyses, topochemical characteristics of this novel solid-state photosolvolysis are discussed.