5,14-pentacenequinone | 6006-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 5,14-pentacenequinone
• 英文别名: 5,14-pentacenedione；pentacene-5,14-dione
• CAS: 6006-83-3
• 化学式: C₂₂H₁₂O₂
• 分子量: 308.336
• InChiKey: WZMPFLVAXXQDRG-UHFFFAOYSA-N

物化性质

• 熔点：
  374 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  557.5±20.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 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：
  2

反应信息

• 作为反应物：
  描述：

  5,14-pentacenequinone 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis, Properties, and Theoretical Characterization of Largely π-Extended Tetrathiafulvalene Derivatives with Quinonoid Structures

  摘要：

  A series of highly conjugated tetrathiafulvalene (TTF) analogues with a quinonoid structure has been synthesized, and their structural and electronic properties have been characterized by both. experimental techniques and quantum-chemical calculations. Cyclic voltammetry measurements show a two-electron oxidation wave to form the dication, which is mainly located on the dithiole rings. The second irreversible oxidation wave to form the trication-radical corresponds to the oxidation of the polyacenic backbone. The temperature dependence of the reduction peak corresponding to the donor(2+) --> donor(0) process is explained in terms of the low stability of the cation and the high aromaticity of the dication. Charge-transfer complexes are formed with the strong acceptor TCNQF(4) showing a 1:2 (D:A) stoichiometry and a semiconducting behavior. The molecular structures of neutral and oxidized compounds are investigated by performing theoretical calculations at the semiempirical, ab initio, and density functional theory levels. The steric hindrance introduced by lateral benzoannulation determines the loss of planarity of the neutral molecules, which adopt butterfly shaped structures. The folded structures are retained in the cations, reducing the gain of aromaticity in the first oxidation step. The dications are by contrast predicted to be fully aromatic and are formed by a planar polyacenic moiety and two orthogonal, singly charged dithiole rings. The destabilization of the cations and the high aromaticity of the dications explain the redox properties observed experimentally. Theoretical calculations also help to rationalize the UV-vis data since they predict the appearance of a low-energy charge-transfer absorption band for the neutral compounds where the laterally fused polyacenic units act as accepters.

  DOI：

  10.1021/jo9719416
• 作为产物：
  描述：

  2-bromo-3-(bromomethyl)naphthalene 在 正丁基锂 、 溶剂黄146 、 calcium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.5h， 生成 5,14-pentacenequinone
  参考文献：
  名称：

  The preparation and reactions of naphtho[1,2-c]furan and naphtho[2,3-c]furan

  摘要：

  DOI：

  10.1021/jo00370a004

文献信息

• Facile Sc(OTf)₃-Catalyzed Generation and Successive Aromatization of Isobenzofuran from <i>o</i>-Dicarbonylbenzenes
  作者：Yuta Nishina、Tatsuya Kida、Tomonari Ureshino

  DOI：10.1021/ol201479p

  日期：2011.8.5

  Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels–Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

  异苯并呋喃可以使用氢化硅烷由邻苯二甲醛制备。形成的异苯并呋喃通过狄尔斯-阿尔德反应被烯烃捕获。进一步脱水以提供共轭芳族化合物。催化量的Sc（OTf）3促进了该多步反应。
• Acene-based organic semiconductor materials and methods of preparing and using the same
  申请人：Facchetti Antonio

  公开号：US20080185555A1

  公开（公告）日：2008-08-07

  Acene-based compounds that can be used to prepare n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including n-type semiconductor materials prepared from these compounds also are provided.

  提供了一种可以用来制备n型半导体材料的基于Acene的化合物，以及制备这些化合物的方法。还提供了由这些化合物制备的n型半导体材料的复合材料和电子器件。
• Functionalized Pentacene:  Improved Electronic Properties from Control of Solid-State Order
  作者：John E. Anthony、James S. Brooks、David L. Eaton、Sean R. Parkin

  DOI：10.1021/ja0162459

  日期：2001.9.1

  two-fold: First, the substituents should impart solubility to the acene, to simplify purification and processing. Second, the substituents should induce some capability for self-assembly of the aromatic moieties into ﷿-stacked arrays to enhance intermolecular orbital overlap. We anticipated that both of these goals could be accomplished by exploiting a rigid spacer to hold the necessarily bulky solubilizing

  分子顺序已被证明是影响基于有机半导体的器件性能的重要因素。最近涉及溶解与未取代噻吩低聚物的研究表明，增加固态轨道重叠的修饰可以将器件性能提高一个数量级以上。1 对并五苯的类似研究，这种化合物已在器件应用中显示出显着的潜力，2 还专注于通过在薄膜中诱导有序来最大化轨道重叠。3 然而，这些并五苯研究迄今为止依赖于底物修饰，而不是并五苯官能化，4 来实现预期目标。我们在这里报告了两种功能化并五苯衍生物的制备，以及这种功能化对所得晶体的固态排序和电子特性的影响。我们对功能化并五苯的目标有两个：首先，取代基应赋予并苯溶解性，以简化纯化和加工。其次，取代基应该诱导芳香部分自组装成﷿堆叠阵列的能力，以增强分子间轨道重叠。我们预计，这两个目标都可以通过利用刚性间隔基使必要的庞大增溶基团远离芳香核来实现，从而使芳香环之间的接触尽可能接近。5 我们最初的目标是双（三异丙基甲硅烷基乙炔基）并五苯 1 和 2。在分别由
• 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。