spiro[9H-fluorene-9,9'-[9H]-xanthene]-2',7'-diol | 2152-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro[9H-fluorene-9,9'-[9H]-xanthene]-2',7'-diol
• 英文别名: Spiro[fluorene-9,9'-xanthene]-2',7'-diol
• CAS: 2152-03-6
• 化学式: C₂₅H₁₆O₃
• 分子量: 364.4
• InChiKey: GYSQGMRKCZPWHK-UHFFFAOYSA-N

物化性质

• 沸点：
  591.1±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-芴酮 、 对苯二酚 、 间苯二酚 在 盐酸 、 十二硫醇 作用下， 以 水 为溶剂， 反应 8.0h， 生成 spiro[9H-fluorene-9,9'-[9H]-xanthene]-2',7'-diol 、 spiro(fluorene-9,9'-xanthene)-2',6'-diol 、 螺[9H-芴-9,9'-[9H]呫吨]-3',6'-二醇
  参考文献：
  名称：

  Symmetric and asymmetric spiro-type colorless poly(ester imide)s with low coefficients of thermal expansion, high glass transition temperatures, and excellent solution-processability

  摘要：

  In this work, we present several new poly(ester imide)s (PEsIs) with low coefficients of thermal expansion (CTE), excellent optical transparency, very high heat resistance (T-g), film ductility, and solution-processability. Symmetric and asymmetric spiro-type tetracarboxylic dianhydrides containing ester linkages (TA-s-Spiro and TA-a-Spiro) and diamines (AB-s-Spiro and AB-a-Spiro) were synthesized using xanthene-based isomeric bi-sphenols with a fluorenyl side group. The chemically imidized PEsIs were highly soluble in various common solvents including less polar non-amide solvents, and yielded stable solutions with high solid contents. The properties of the spiro-type PEsIs were systematically investigated and compared with those of the cardo-type counterparts. A PEsI derived from 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), AB-a-Spiro, and 2,2'-bis( trifluoromethyl) benzidine (TFMB) achieved outstanding combined properties, i.e., a very low CTE (10.5 ppm K-1), excellent optical transparency (YI = 3.4, T-400 = 80.8%), a very high T-g (351 degrees C) and solution-processability. Thus, the PEsIs are promising candidates as novel plastic substrates for use in image display devices. The isomer effects on the properties were also investigated and a possible mechanism for these effects is proposed.

  DOI：

  10.1016/j.polymer.2019.02.020

文献信息

• CHLORINATION PROCESS, ALKYLATION OF PRODUCTS OF SAID PROCESS AND SOME PRODUCTS THEREOF
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0611366A1

  公开（公告）日：1994-08-24
• US5387725A
  申请人：——

  公开号：US5387725A

  公开（公告）日：1995-02-07
• US5578737A
  申请人：——

  公开号：US5578737A

  公开（公告）日：1996-11-26
• [EN] CHLORINATION PROCESS, ALKYLATION OF PRODUCTS OF SAID PROCESS AND SOME PRODUCTS THEREOF
  申请人：——

  公开号：WO1993009074A2

  公开（公告）日：1993-05-13

  [EN] Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is a tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.
  [FR] On effectue la chloration de composés possédant des protons acides et une structure moléculaire pouvant délocaliser la densité d'électrons de la base du conjugué (composés cible) en les mettant en contact avec un perchloroalcane et une base aqueuse en présence d'un catalyseur de transfert de phase qui est un hydroxyde de tétra-alkylammonium. On obtient des produits chlorés, de préference, des composés gem-dichloro, c'est-à-dire, possédant deux atomes de chlore sur le même atome de carbone. Lesdits composés gem-dichloro sont efficaces pour l'alkylation de composés aromatiques. Par exemple, on effectue la chloration du fluorène, afin d'obtenir du 9,9-dichlorofluorène qu'on fait réagir avec des composés tels que le phénol ou l'aniline, afin d'obtenir des composés de 9,9-bis(hydroxyphényl)fluorène, 9,9-bis(aminophényl)fluorène ou 9-aminophényle-9-chlorofluorène.
• Symmetric and asymmetric spiro-type colorless poly(ester imide)s with low coefficients of thermal expansion, high glass transition temperatures, and excellent solution-processability
  作者：Masatoshi Hasegawa、Shinya Takahashi、Soichi Tsukuda、Tomoki Hirai、Junichi Ishii、Yukari Yamashina、Yoshinori Kawamura

  DOI：10.1016/j.polymer.2019.02.020

  日期：2019.4

  In this work, we present several new poly(ester imide)s (PEsIs) with low coefficients of thermal expansion (CTE), excellent optical transparency, very high heat resistance (T-g), film ductility, and solution-processability. Symmetric and asymmetric spiro-type tetracarboxylic dianhydrides containing ester linkages (TA-s-Spiro and TA-a-Spiro) and diamines (AB-s-Spiro and AB-a-Spiro) were synthesized using xanthene-based isomeric bi-sphenols with a fluorenyl side group. The chemically imidized PEsIs were highly soluble in various common solvents including less polar non-amide solvents, and yielded stable solutions with high solid contents. The properties of the spiro-type PEsIs were systematically investigated and compared with those of the cardo-type counterparts. A PEsI derived from 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), AB-a-Spiro, and 2,2'-bis( trifluoromethyl) benzidine (TFMB) achieved outstanding combined properties, i.e., a very low CTE (10.5 ppm K-1), excellent optical transparency (YI = 3.4, T-400 = 80.8%), a very high T-g (351 degrees C) and solution-processability. Thus, the PEsIs are promising candidates as novel plastic substrates for use in image display devices. The isomer effects on the properties were also investigated and a possible mechanism for these effects is proposed.