1,8-difluoropentacene-6,13-dione | 854519-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯醌
• 英文名称: 1,8-difluoropentacene-6,13-dione
• CAS: 854519-93-0
• 化学式: C₂₂H₁₀F₂O₂
• 分子量: 344.317
• InChiKey: BZORCVVMXTVHAO-UHFFFAOYSA-N

物化性质

• 沸点：
  562.5±40.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氟邻二甲苯 、 对苯醌 在 N-溴代丁二酰亚胺(NBS) 、 potassium iodide 作用下， 以 四氯化碳 、 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 生成 1,11-difluoropentacene-6,13-dione 、 1,8-difluoropentacene-6,13-dione
  参考文献：
  名称：

  迈向可溶液处理的空气稳定型p型有机半导体：单和二氟化并五苯衍生物的合成和评估†

  摘要：

  报道了一系列用作有机半导体的单氟化和二氟化TIPS并五苯化合物的合成。即新型的1-氟-6,13-​​双[三异丙基甲硅烷基-乙炔基]并五苯（1-氟-TIPS-并五苯），2-氟-TIPS-并五苯以及最近报道的1：1顺 ： 反异构体混合物1， （8:11）-二氟-TIPS-戊烯和2，（9:10）-二氟-TIPS-戊烯。这些材料首次进行了分子结构与热/光化学稳定性之间关系的研究。并五苯HOMO的变化通过研究了氟取代的变化及其与环境稳定性的关系。如所预测的，发现增加吸电子的氟取代基的数量增加了对光降解的稳定性。还观察到，当氟存在于靠近中心环的1-和1，（8:11）-位置而不是2-和2，（9:10）-时，稳定性增加（而HOMO降低）。职位。与未衍生的TIPS-并五苯相比，含氟衍生物的比较晶体管测量结果显示出具有竞争力的器件性能。通过首次对该系列进行比较，已完成了这些材料的完整表征和NMR分配。

  DOI：

  10.1039/c6tc01221c

文献信息

• [EN] SILYLETHYNYL PENTACENE COMPOUNDS AND COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPOSÉS DE SILYLÉTHYNYLE PENTACÈNE ET COMPOSITIONS ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CEUX-CI
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2009155106A1

  公开（公告）日：2009-12-23

  Silylethynyl pentacenes and compositions containing silylethynyl pentacenes are disclosed. Exemplary pentacene compounds have 6, 13 -silylethynyl substitution with one or more groups (e.g., R, R' and R") covalently bonded to each Si atom of the silylethynyl groups. Methods of making and using silylethynyl pentacenes and compositions containing silylethynyl pentacenes are also disclosed. Substrates and devices comprising the silylethynyl pentacenes and compositions are also disclosed.

  揭示了含有硅基乙炔基戊二烯和含有硅基乙炔基戊二烯的组合物。示例戊二烯化合物具有6,13-硅基乙炔基取代物，其中一个或多个基团（例如，R、R'和R"）共价键合到硅基乙炔基的每个Si原子。还公开了制备和使用硅基乙炔基戊二烯和含有硅基乙炔基戊二烯的组合物的方法。还公开了包含硅基乙炔基戊二烯和组合物的基板和器件。
• Organic semiconducting layers
  申请人：Brown Beverley

  公开号：US20070102696A1

  公开（公告）日：2007-05-10

  An organic semiconducting layer formulation, which comprises: an organic binder which has a permittivity, ∈, at 1,000 Hz of 3.3 or less; and a polyacene compound of Formula: A: wherein: each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and (R 12 , which may be the same or different, independently represents hydrogen; an optionally substituted C 1 -C 40 carbyl or hydrocarbyl group; an optionally substituted C 1 -C 40 alkoxy group; an optionally substituted C 6 -C 40 aryloxy group; an optionally substituted C 7 -C 40 alkylaryloxy group; an optionally substituted C 2 -C 40 alkoxycarbonyl group; an optionally substituted C 7 -C 40 aryloxycarbonyl group; a cyano group (—CN); a carbamoyl group (—C(═O)NH 2 ); a haloformyl group (—C(═O)—X, wherein X represents a halogen atom); a formyl group (—C(═O)—H); an isocyano group; an isocyanate group; a thiocyanate group or a thioisocyanate group; an optionally substituted amino group; a hydroxy group; a nitro group; a CF 3 group; a halo group (CI, Br, F); or an optionally substituted silyl group; and wherein independently each pair of R 2 and R 3 and/or R 8 and R 9 , may be cross-bridged to form a C 4 -C 40 saturated or unsaturated ring, which saturated or unsaturated ring may be intervened by an oxygen atom, a sulphur atom or a group shown by formula —N(R a )— (wherein R a is a hydrogen atom or an optionally substituted hydrocarbon group), or may optionally be substituted; and wherein one or more of the carbon atoms of the polyacene skeleton may optionally be substituted by a heteroatom selected from O N, P, As, O, S, Se and Te; and wherein independently any two or more of the substituents R 1 -R 12 which are located on adjacent ring positions of the polyacene may, together, optionally constitute a further C 4 -C 40 saturated or unsaturated ring optionally interrupted by O, S or —N(R a ) where R a is as defined above) or an aromatic ring system, fused to the polyacene; and wherein n is 0, 1, 2, 3 or 4, also claimed is an electronic device, particularly an organic field effect transistor comprising the organic semiconductor layer formulation.

  一种有机半导体层配方，包括：具有介电常数在1,000 Hz时为3.3或更低的有机粘合剂；以及式子A的聚芳烃化合物： 其中，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和（R12，可以相同或不同，独立地代表氢；可选地取代的C1-C40卡烷基或烃基；可选地取代的C1-C40烷氧基；可选地取代的C6-C40芳氧基；可选地取代的C7-C40烷基芳氧基；可选地取代的C2-C40烷氧羰基基团；可选地取代的C7-C40芳氧羰基基团；氰基（—CN）；氨基甲酰基（—C（═O）NH2）；卤甲基基团（—C（═O）—X，其中X代表卤素原子）；甲酰基（—C（═O）—H）；异氰基基团；异氰酸酯基团；硫氰酸基团或硫代异氰酸基团；可选地取代的氨基团；羟基；硝基；CF3基团；卤素基团（CI，Br，F）；或可选地取代的硅基团；其中，独立地，R2和R3和/或R8和R9的任意一对可以通过交叉桥接形成一个饱和或不饱和的C4-C40环，该饱和或不饱和的环可以由氧原子，硫原子或由式子—N（Ra）—（其中Ra是氢原子或可选地取代的碳氢基团）所示的基团介入，或者可以可选地被取代；聚芳烃骨架的一个或多个碳原子可以可选地被从O、N、P、As、O、S、Se和Te中选择的杂原子所取代；独立地，位于聚芳烃上相邻环位置的两个或多个取代基R1-R12中的任意两个或多个，可以一起可选地构成进一步的C4-C40饱和或不饱和环，该环可被O、S或—N（Ra）（其中Ra如上定义）或融合到聚芳烃中的芳香环系统中打断；n为0、1、2、3或4。此外，还声明了一种电子器件，特别是包括有机半导体层配方的有机场效应晶体管。
• ORGANIC SEMICONDUCTING LAYERS
  申请人：Brown Anne Beverley

  公开号：US20070137520A1

  公开（公告）日：2007-06-21

  An organic semiconducting layer formulation, which comprises: an organic binder which has a permittivity, ε, at 1,000 Hz of 3.3 or less; and a polyacene compound of Formula: A: wherein: each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 , which may be the same or different, independently represents hydrogen; an optionally substituted C 1 -C 40 carbyl or hydrocarbyl group; an optionally substituted C 1 -C 40 alkoxy group; an optionally substituted C 6 -C 40 aryloxy group; an optionally substituted C 7 -C 40 alkylaryloxy group; an optionally substituted C 2 -C 40 alkoxycarbonyl group; an optionally substituted C 7 -C 40 aryloxycarbonyl group; a cyano group (—CN); a carbamoyl group (—C(═O)NII 2 ); a haloformyl group (—C(═O)—X, wherein X represents a halogen atom); a formyl group (—C(═O)—H); an isocyano group; an isocyanate group; a thiocyanate group or a thioisocyanate group; an optionally substituted amino group; a hydroxy group; a nitro group; a CF 3 group; a halo group (Cl, Br, F); or an optionally substituted silyl group; and wherein independently each pair of R 2 said R 3 and/or R 8 and R 9 , may be cross-bridged to form a C 4 -C 40 saturated or unsaturated ring, which saturated or unsaturated ring may be intervened by an oxygen atom, a sulphur atom or a group shown by formula —N(R a )— (wherein R a is a hydrogen atom or an optionally substituted hydrocarbon group), or may optionally be substituted; and wherein one or more of the carbon atoms of the polyacene skeleton may optionally be substituted by a heteroatom selected from N, P, As, O, S, Se and Te; and wherein independently any two or more of the substituent R 1 —R 12 which are located on adjacent ring positions of the polyacene may, together, optionally constitute a further C 4 -C 40 saturated or unsaturated ring optionally interrupted by O, S or —N(R a ) where R a is as defined above) or an aromatic ring system, fused to the polyacene; and wherein n is 0, 1, 2, 3 or 4, also claimed is an electronic device, particularly an organic field effect transistor comprising the organic semiconductor layer formulation.

  一种有机半导体层组合物，包括：具有在1,000 Hz时介电常数ε为3.3或以下的有机粘合剂；以及Formula A的多聚芳烃化合物：其中：R1，R2，R3，R4，R5，R6，R7，R8，R9，R10，R11和R12中的每一个，可以相同或不同地独立地表示氢；一个可选取代的C1-C40卡比尔或烃基；一个可选取代的C1-C40烷氧基；一个可选取代的C6-C40芳氧基；一个可选取代的C7-C40烷基芳氧基；一个可选取代的C2-C40烷氧羰基；一个可选取代的C7-C40芳基氧羰基；一个氰基（-CN）；一个氨基甲酰基（-C（═O）NII2）；一个卤甲基（-C（═O）-X，其中X表示卤素原子）；一个甲酰基（-C（═O）-H）；一个异氰基；一个异氰酸酯基；一个硫氰酸酯基或硫代异氰酸酯基；一个可选取代的氨基；一个羟基；一个硝基；一个CF3基团；一个卤素基团（Cl，Br，F）；或一个可选取代的硅基团；其中，独立地，R2所述的R3和/或R8和R9中的每一对，可以交叉桥接形成一个C4-C40饱和或不饱和的环，该饱和或不饱和的环可以由氧原子，硫原子或由式子-N（Ra）-（其中Ra是氢原子或可选取代的碳氢基团）所示的基团介入，或者可以可选地被取代；并且其中多聚芳烃骨架的一个或多个碳原子可以可选地被从N、P、As、O、S、Se和Te中选择的杂原子取代；独立地，多个置于多聚芳烃上的取代基R1-R12中的任意两个或更多个，可以一起可选地构成进一步的C4-C40饱和或不饱和环，可选地被O、S或-N（Ra）（其中Ra如上定义）或融合到多聚芳烃的芳香环系中打断；其中n为0、1、2、3或4，还声明了一种电子器件，特别是包括该有机半导体层组合物的有机场效应晶体管。
• Organic semiconductor layers
  申请人：Brown Anne Beverley

  公开号：US20080009625A1

  公开（公告）日：2008-01-10

  An organic semiconducting layer formulation, which comprises: an organic binder which has a permittivity, ε, at 1,000 Hz of 3.3 or less; and a polyacene compound of Formula: (A) wherein: each of R 1 , R 2 , R 3 , R, R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 , which may be the same or different, independently represents hydrogen; an optionally substituted C 1 -C 40 carbyl or hydrocarbyl group; an optionally substituted C 1 -C 40 alkoxy group; an optionally substituted C 6 -C 40 aryloxy group; an optionally substituted C 7 -C 40 alkylaryloxy group; an optionally substituted C 2 -C 40 alkoxycarbonyl group; an optionally substituted C 7 -C 40 aryloxycarbonyl group; a cyano group (—CN); a carbamoyl group (—C(═O)NH 2 ); a haloformyl group (—C(═O)—X, wherein X represents a halogen atom); a formyl group (—C(═O)—H); an isocyano group; an isocyanate group; a thiocyanate group or a thioisocyanate group; an optionally substituted amino group; a hydroxy group; a nitro group; a CF 3 group; a halo group (CI, Br, F); or an optionally substituted silyl group; and wherein independently each pair of R 2 and R 3 and/or R 8 and R 9 , may be cross-bridged to form a C 4 -C 40 saturated or unsaturated ring, which saturated or unsaturated ring may be intervened by an oxygen atom, a sulphur atom or a group shown by formula —N(R a )— (wherein R a is a hydrogen atom or an optionally substituted hydrocarbon group), or may optionally be substituted; and wherein one or more of the carbon atoms of the polyacene skeleton may optionally be substituted by a heteroatom selected from N, P, As, O, S, Se and Te; and wherein independently any two or more of the substituents R 1 —R 12 which are located on adjacent ring positions of the polyacene may, together, optionally constitute a further C 4 -C 40 saturated or unsaturated ring optionally interrupted by O, S or —N(R a ) where R a is as defined above) or an aromatic ring system, fused to the polyacene; and wherein n is 0, 1, 2, 3 or 4, also claimed is an electronic device, particularly an organic field effect transistor comprising the organic semiconductor layer formulation.

  一种有机半导体层配方，包括：具有1,000 Hz下介电常数ε小于或等于3.3的有机粘合剂；以及式子（A）的聚芴化合物：其中：R1、R2、R3、R、R5、R6、R7、R8、R9、R10、R11和R12中的每一个，可以相同或不同，独立地表示氢；可选取代的C1-C40卡宾基或烃基；可选取代的C1-C40烷氧基；可选取代的C6-C40芳氧基；可选取代的C7-C40烷基芳氧基；可选取代的C2-C40烷氧羰基；可选取代的C7-C40芳氧羰基；氰基（—CN）；氨基甲酰基（—C(═O)NH2）；卤甲基基（—C(═O)—X，其中X表示卤素原子）；甲酰基（—C(═O)—H）；异氰基；异氰酸酯基；硫氰酸酯基或硫代异氰酸酯基；可选取代的氨基；羟基；硝基；CF3基；卤素基（CI，Br，F）；或可选取代的硅基；独立地，R2和R3和/或R8和R9中的每一对，可以交叉桥接形成一个C4-C40饱和或不饱和环，该饱和或不饱和环可以由氧原子、硫原子或由式子—N(Ra)—（其中Ra是氢原子或可选取代的碳氢基团）所示的基团介入，或者可以选择地被取代；聚芴骨架的一个或多个碳原子可以选择地被N、P、As、O、S、Se和Te中选择的杂原子所取代；独立地，位于聚芴上相邻环位置的任意两个或多个取代基R1-R12可以一起选择地构成进一步的C4-C40饱和或不饱和环，可选择地由O、S或—N(Ra)(其中Ra如上定义)中断，或者融合到聚芴上的芳香环系统中；n为0、1、2、3或4。还包括一种电子设备，特别是包括该有机半导体层配方的有机场效应晶体管。
• Silylethynyl Pentacene Compounds and Compositions and Methods of Making and Using the Same
  申请人：Caldwell Gregg Alexander

  公开号：US20110073813A1

  公开（公告）日：2011-03-31

  Silylethynyl pentacenes and compositions containing silylethynyl pentacenes are disclosed. Exemplary pentacene compounds have 6,13-silylethynyl substitution with one or more groups (e.g., R, R′ and R″) covalently bonded to each Si atom of the silylethynyl groups. Methods of making and using silylethynyl pentacenes and compositions containing silylethynyl pentacenes are also disclosed. Substrates and devices comprising the silylethynyl pentacenes and compositions are also disclosed.

  本发明公开了含有硅基乙炔基五环芴化合物的组合物。其中，举例的五环芴化合物具有6,13-硅基乙炔基取代基，且每个硅基乙炔基的Si原子上共价键结合有一个或多个基团（例如，R、R′和R″）。本发明还公开了制备和使用硅基乙炔基五环芴化合物及其组合物的方法。本发明还公开了包含硅基乙炔基五环芴化合物和组合物的基板和器件。