anthra[2,3-b:7,6-b’]dithiophene-5,11-dione | 143746-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthra[2,3-b:7,6-b’]dithiophene-5,11-dione
• 英文别名: 6,18-dithiapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(13),3(11),4,7,9,14,16,19-octaene-2,12-dione
• CAS: 143746-71-8
• 化学式: C₁₈H₈O₂S₂
• 分子量: 320.392
• InChiKey: VMWHYUMDCWRVNB-UHFFFAOYSA-N

物化性质

• 沸点：
  569.3±40.0 °C(predicted)
• 密度：
  1.553±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 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：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三异丙基硅基乙炔 、 anthra[2,3-b:7,6-b’]dithiophene-5,11-dione 在 正丁基锂 、 盐酸 、 tin(ll) chloride 作用下， 以 正己烷 、 水 为溶剂， 反应 3.0h， 以38%的产率得到5,11-bis(triisopropylsilylethynyl)anthra[2,3-b:7,6-b']dithiophene
  参考文献：
  名称：

  [EN] SYNTHESIS OF NEW SMALL MOLECULES/OLIGOMERS WITH HIGH CONDUCTIVITY AND ABSORPTION FOR OPTOELECTRONIC APPLICATION
  [FR] SYNTHÈSE DE NOUVELLES PETITES MOLÉCULES/OLIGOMÈRES À HAUTE CONDUCTIVITÉ ET À FORTE ABSORPTION POUR APPLICATION OPTO-ÉLECTRONIQUE

  摘要：

  揭示了包含一个中心、富电子的、功能化的二氢二环戊基蒽核（或电子供体核心）的半导体或导电有机小分子和寡聚物，该核心连接至至少一个或两个相对电子亏缺的单体单元（或电子受体单元），该单元具有第16族杂原子硫、硒或碲或其组合。多个富电子核心可以通过一个或多个炔基连接在一起。这些小分子和寡聚物可以具有以下通用结构，并可用于有机光伏材料等领域。

  公开号：

  WO2015166360A1
• 作为产物：
  描述：

  C₂₄H₂₆O₇S₂ 在 indium(III) triflate 作用下， 以 丙酮 为溶剂， 以81%的产率得到anthra[2,3-b:7,6-b’]dithiophene-5,11-dione
  参考文献：
  名称：

  Hexathienocoronenes: Synthesis and Self-Organization

  摘要：

  Here we report hexathienocoronenes (HTCs), fully thiophene-annelated coronenes in which six double bonds in the periphery are thieno-fused. The derivatives tetrasubstituted with hexyl and dodecyl chains show a phase formation that strongly depends on the chain length. HTCs are remarkably stronger donors than the known thiophene-annelated coronenes but do not readily assemble into well-ordered films when deposited from the vapor phase. Thus, thin-film transistors fabricated by vacuum deposition have only modest field-effect mobilities of 0.002 cm(2) V-1 s(-1).

  DOI：

  10.1021/ja3082395

文献信息

• Stable, Crystalline Acenedithiophenes with up to Seven Linearly Fused Rings
  作者：Marcia M. Payne、Susan A. Odom、Sean R. Parkin、John E. Anthony

  DOI：10.1021/ol048686d

  日期：2004.9.1

  [structure: see text] We report the synthesis of a series of crystalline acenedithiophenes with up to seven linearly fused rings and silylethynyl substituents. These functional groups are designed to both improve solubility and enhance cofacial interactions in the solid. We discuss the crystal packing of these materials, as well as their physical properties such as oxidation potential, UV-vis absorption

  [结构：见正文]我们报告了一系列具有多达七个线性稠合环和甲硅烷基乙炔基取代基的结晶a庚二烯噻吩的合成。这些官能团被设计为既改善溶解度又增强固体中的界面相互作用。我们讨论了这些材料的晶体堆积，以及它们的物理性质，例如氧化电位，UV-vis吸收，荧光发射和分解途径。
• Low band-gap D-A conjugated copolymers based on anthradithiophene and diketopyrrolopyrrole for polymer solar cells and field-effect transistors
  作者：Jun Huang、Yongxiang Zhu、Lianjie Zhang、Ping Cai、Xiaofeng Xu、Junwu Chen、Yong Cao

  DOI：10.1002/pola.27163

  日期：2014.6.15

  Two conjugated copolymers PADT‐DPP and PADT‐FDPP based on anthradithiophene and diketopyrrolopyrrole, with thiophene and furan as the π‐conjugated bridge, respectively, were successfully synthesized and characterized. The number‐averaged molecular weights of the two polymers are 38.7 and 30.2 kg/mol, respectively. Polymers PADT‐DPP and PADT‐FDPP exhibit broad absorption bands and their optical band

  成功地合成和表征了两种基于蒽噻吩和二酮吡咯并吡咯的共轭共聚物PADT-DPP和PADT-FDPP，分别以噻吩和呋喃为π共轭桥。两种聚合物的数均分子量分别为38.7和30.2 kg / mol。聚合物PADT-DPP和PADT-FDPP表现出较宽的吸收带，其光学带隙分别为1.44和1.50 eV。PADT-DPP的最高占据分子轨道能级为-5.03 eV，而PADT-FDPP的最高分子轨道能级为-5.16 eV。在场效应晶体管中，PADT-DPP和PADT-FDPP的空穴迁移率分别为4.7×10 -3和2.7×10 -3 cm 2/（V s）分别。在聚合物太阳能电池中，PADT-DPP和PADT-FDPP的功率转换效率（PCE）分别为3.44％和0.29％。原子力显微镜显示，PADT-FDPP效率低下应与其活性层中较大的两相分离有关。如果使用1,8-二碘辛烷（DIO）作为溶剂添加剂，由于形态变
• Silylethynylated heteroacenes and electronic devices made therewith
  申请人：University of Kentucky Research Foundation

  公开号：US07385221B1

  公开（公告）日：2008-06-10

  Novel silylethynylated heteroacenes and electronic devices made with those compounds are disclosed.

  揭示了新型硅基炔基杂环芳烃和由这些化合物制成的电子器件。
• 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。