3,4,5-trifluoro-o-benzenedicarboxylic acid anhydride | 1982348-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,4,5-trifluoro-o-benzenedicarboxylic acid anhydride
• 英文别名: trifluoro-o-benzenedicarboxylic acid anhydride；3,4,5-trifluorophthalic acid anhydride；3,4,5-trifluorophthalic anhydride；trifluorophthalic anhydride；4,5,6-Trifluoro-1,3-dihydro-2-benzofuran-1,3-dione；4,5,6-trifluoro-2-benzofuran-1,3-dione
• CAS: 1982348-21-9
• 化学式: C₈HF₃O₃
• 分子量: 202.089
• InChiKey: MCXWABSMXKULCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰乙酸叔丁酯 、 3,4,5-trifluoro-o-benzenedicarboxylic acid anhydride 在 乙酸酐 、 三乙胺 作用下， 反应 12.0h， 以34%的产率得到
  参考文献：
  名称：

  Fluorination Effects on Indacenodithienothiophene Acceptor Packing and Electronic Structure, End-Group Redistribution, and Solar Cell Photovoltaic Response

  摘要：

  Indacenodithienothiophene (IDTT)-based postfullerene electron acceptors, such as ITIC (2,2'-[[6,6,12,12-tetrakis (4-hexylphenyl)-6,12-dihydrodithie no [2,3-d:2',3'-d']-s-indaceno [1,2-b:5,6-b']dithiophene-2,8-diyl]-bis-[methylidyne(3-oxo-1H-indene-2,1 (3H)-diylidene) This[propanedinitrile]), have become synonymous with high power conversion efficiencies (PCEs) in bulk heterojunction (BHJ) polymer solar cells (PSCs). Here we systematically investigate the influence of end-group fluorination density and positioning on the physicochemical properties, single-crystal packing, end-group redistribution propensity, and BHJ photovoltaic performance of a series of ITIC variants, ITIC-nF (n = 0, 2, 3, 4, and 6). Increasing n from 0 -> 6 contracts the optical bandgap, but only marginally lowers the LUMO for n > 4. This yields enhanced photovoltaic short-circuit current density and good open-circuit voltage, so that ITIC-6F achieves the highest PCE of the series, approaching 12% in blends with the PBDB-TF donor polymer. Single-crystal diffraction reveals that the ITIC-nF molecules cofacially interleave with ITIC-6F having the shortest pi-pi distance of 3.28 angstrom. This feature together with ZINDO-level computed intermolecular electronic coupling integrals as high as 57 meV, and B3LYP/DZP-level reorganization energies as low as 147 meV, rival or surpass the corresponding values for fullerenes, ITIC-OF, and ITIC-4F, and track a positive correlation between the ITIC-nF space-charge limited electron mobility and n. Finally, a heretofore unrecognized solution-phase redistribution process between the 2-(3-oxoindan-1-ylidene)-malononitrile-derived end-groups (EGs) of IDTT-based NFAs, i.e., EG(1)-IDTT-EG(1) + EG(2)-IDTT-EG(2) reversible arrow 2 EG(1)-IDTT-EG(2), with implications for the entire ITIC PSC field, is identified and mechanistically characterized, and the effects on PSC performance are assessed.

  DOI：

  10.1021/jacs.8b13653
• 作为产物：
  描述：

  3,4,5-三氟苯甲酸 在 正丁基锂 、 乙酸酐 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.0h， 生成 3,4,5-trifluoro-o-benzenedicarboxylic acid anhydride
  参考文献：
  名称：

  Fluorination Effects on Indacenodithienothiophene Acceptor Packing and Electronic Structure, End-Group Redistribution, and Solar Cell Photovoltaic Response

  摘要：

  Indacenodithienothiophene (IDTT)-based postfullerene electron acceptors, such as ITIC (2,2'-[[6,6,12,12-tetrakis (4-hexylphenyl)-6,12-dihydrodithie no [2,3-d:2',3'-d']-s-indaceno [1,2-b:5,6-b']dithiophene-2,8-diyl]-bis-[methylidyne(3-oxo-1H-indene-2,1 (3H)-diylidene) This[propanedinitrile]), have become synonymous with high power conversion efficiencies (PCEs) in bulk heterojunction (BHJ) polymer solar cells (PSCs). Here we systematically investigate the influence of end-group fluorination density and positioning on the physicochemical properties, single-crystal packing, end-group redistribution propensity, and BHJ photovoltaic performance of a series of ITIC variants, ITIC-nF (n = 0, 2, 3, 4, and 6). Increasing n from 0 -> 6 contracts the optical bandgap, but only marginally lowers the LUMO for n > 4. This yields enhanced photovoltaic short-circuit current density and good open-circuit voltage, so that ITIC-6F achieves the highest PCE of the series, approaching 12% in blends with the PBDB-TF donor polymer. Single-crystal diffraction reveals that the ITIC-nF molecules cofacially interleave with ITIC-6F having the shortest pi-pi distance of 3.28 angstrom. This feature together with ZINDO-level computed intermolecular electronic coupling integrals as high as 57 meV, and B3LYP/DZP-level reorganization energies as low as 147 meV, rival or surpass the corresponding values for fullerenes, ITIC-OF, and ITIC-4F, and track a positive correlation between the ITIC-nF space-charge limited electron mobility and n. Finally, a heretofore unrecognized solution-phase redistribution process between the 2-(3-oxoindan-1-ylidene)-malononitrile-derived end-groups (EGs) of IDTT-based NFAs, i.e., EG(1)-IDTT-EG(1) + EG(2)-IDTT-EG(2) reversible arrow 2 EG(1)-IDTT-EG(2), with implications for the entire ITIC PSC field, is identified and mechanistically characterized, and the effects on PSC performance are assessed.

  DOI：

  10.1021/jacs.8b13653

文献信息

• PRODUCTION METHOD OF HALOGEN-SUBSTITUTED PHTHALIDE
  申请人：Hagiya Koji

  公开号：US20120142946A1

  公开（公告）日：2012-06-07

  Disclosed is a method for producing a halogen-substituted phthalide, which includes a reaction step of reacting a halogen-substituted phthalic anhydride with sodium borohydride.

  本发明公开了一种制备卤代邻苯二酸酐的方法，其中包括将卤代邻苯二酸酐与硼氢化钠反应的反应步骤。
• Radiation crosslinkable compositions
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0329298A2

  公开（公告）日：1989-08-23

  Aqueous solvent dispersible, radiation crosslinkable compounds and oligomers containing poly(ethylenically unsaturated) group-containing components and carboxyl groups are disclosed. Each compound is a monester of a cyclic dicarboxylic acid anhydride and a 2-hydroxyalkylpolyester, said 2-hydroxyalkylpolyester being the ester Jf a polyepoxide with a monoester which is the monoester of a poly(ethylenically-unsaturated)alkanol and a dicarboxylic acid. These compounds and oligomers are useful in the field of graphic arts and protective coatings.

  本发明公开了可在水性溶剂中分散、可辐射交联的化合物和低聚物，其中含有聚（乙烯不饱和）基团成分和羧基。每种化合物都是环状二羧酸酐和 2-羟基烷基聚酯的单酯，所述 2-羟基烷基聚酯是聚环氧化物与单酯的酯 Jf，单酯是聚(乙烯不饱和)烷醇和二羧酸的单酯。这些化合物和低聚物可用于图形艺术和保护涂层领域。
• ZIEGLER-NATTA CATALYST FOR OLEFIN POLYMERIZATION
  申请人：Hyosung Corporation

  公开号：EP2520594A2

  公开（公告）日：2012-11-07

  The present invention relates to a Ziegler-Natta catalyst, and more specifically to a Ziegler-Natta catalyst for olefin polymerization which may use a compound of Formula 3 as an internal electron donor to obtain polymers with high activity, wide molecular weight distribution and low content of fine particle.

  本发明涉及一种齐格勒-纳塔催化剂，更具体地说，涉及一种用于烯烃聚合的齐格勒-纳塔催化剂，该催化剂可使用式 3 的化合物作为内部电子供体，以获得活性高、分子量分布广和细颗粒含量低的聚合物。
• PRODUCTION METHOD OF TRI- OR TETRAHALOGEN-SUBSTITUTED PHTHALIDE
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2433933B1

  公开（公告）日：2019-05-08
• 2-ARYL-3-(AMINOARYL)-3-(HYDROXYARYL)PHTHALIMIDINE COMPOUNDS AND METHODS FOR MAKING THEM
  申请人：General Electric Company, (a New York Corporation)

  公开号：EP1957456A1

  公开（公告）日：2008-08-20