1,3-dibromo-5-{5'-(2',2''-bithienyl)}benzene | 651329-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 1,3-dibromo-5-{5'-(2',2''-bithienyl)}benzene
• 英文别名: 5-(3,5-dibromophenyl)-2,2'-bithiophene；2-(3,5-dibromophenyl)-5-thiophen-2-ylthiophene
• CAS: 651329-37-2
• 化学式: C₁₄H₈Br₂S₂
• 分子量: 400.158
• InChiKey: BJRLIJAXUVPMJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硼酸三甲酯 、 2,2'-联二噻吩 在 正丁基锂 、 ammonium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 以73%的产率得到2,2’-联噻吩-5-硼酸
  参考文献：
  名称：

  METHOD FOR PRODUCING A ENDRIMER, BUILDING BLOCK COMPOUND, AND METHOD FOR PRODUCING A THIOPHENE COMPOUND

  摘要：

  公开号：

  EP1535942B1

文献信息

• Meta-Substituted Thienyl Benzenes: A Comparative Synthetic, Structural and Computational Study
  作者：Angelica L. P. Cornacchio、Jacquelyn T. Price、Michael C. Jennings、Robert McDonald、Viktor N. Staroverov、Nathan D. Jones

  DOI：10.1021/jo801771d

  日期：2009.1.16

  meta-substituted phenyl-cored dendrimers were predominantly responsible for absorption and that excitons were localized to the “arms” without any electronic coupling between them, but also introduced the caveat that there was a minimum of two contiguous thiophene rings required for strict exciton localization to the arms. The oxidation potentials of the compounds in solution ranged from 0.9 to 1.6 V and were

  在一系列间位取代的噻吩苯（T n）2 C 6 H 4和（T n）3 C 6 H 3（n = 1，2; T 1 = 2-噻吩基; T 2 = 2,2'-bithien-5-基）。PdCl 2催化的熊田偶联反应就便利性，选择性和收率而言，发现合适的噻吩基格氏与1,3-或1,3,5-溴或碘苯之间的（dppf）是最可靠的（dppf = 1,1'-bis（二苯基膦）二茂铁）。这些条件也使混合的（噻吩基）（卤）苯，（T n）C 6 H 3 X 2和（T n）2 C 6 H 3 X（X = Br，I）最优化合成。后者的溴化物可在随后的Stille，Sonogashira或Kumada反应中进一步完善，以提供在第三个间位（T n）2 C 6带有供电子或吸电子基团的双（噻吩基）化合物H 3 R（R = Ph，p -MeOC 6 H 4，p -FC 6 H 4 ; n = 1，2）和（T 1）2 C 6 H 3
• PROCESS FOR PRODUCING DENDRIMER, BUILDING BLOCK COMPOUND, AND PROCESS FOR PRODUCING THIOPHENE COMPOUND
  申请人：Toyo Gosei Co., Ltd.

  公开号：EP1535942A1

  公开（公告）日：2005-06-01

  A method for producing a dendrimer having a structural repeating unit which is represented by formula (1) and which contains a linear portion including a thienylene moiety and a branch portion Y formed of an optionally substituted trivalent organic group. The method is based on the convergent method and includes reaction step 1 of converting α-position hydrogen of the thiophene ring of a thienylene-moiety-containing compound (a) for forming end moieties to an active group V1 which undergoes Suzuki cross-coupling reaction, to thereby form compound (b); reaction step 2 of subjecting a compound (c) to Suzuki cross-coupling reaction with the compound (b), to thereby yield compound (d), the compound (c) having a linear portion and a branch portion Y and having, at the branch portion Y, two active groups V2 which undergo Suzuki cross-coupling reaction with the active group V1; reaction step 3 of converting α-position hydrogen of the thiophene ring of the thus-formed compound to an active group V1 which undergoes Suzuki cross-coupling reaction, and reacting the compound (c) with the active group V1, to thereby form a dendron of a subsequent generation; and a step of repeating the reaction step 3 in accordance with needs, to thereby form a dendrimer.

  一种生产树枝状聚合物的方法，该树枝状聚合物具有结构重复单元，其结构重复单元由式（1）表示，包含包括噻吩分子的线性部分和由任选取代的三价有机基团形成的分支部分Y。该方法以聚合法为基础，包括反应步骤 1：将含噻吩基化合物（a）的噻吩环的α位氢转化为活性基团 V1，使其发生铃木交叉偶联反应，从而形成化合物（b）；反应步骤 2：将化合物（c）与化合物（b）进行铃木交叉偶联反应，从而生成化合物（d），化合物（c）具有线性部分和分支部分 Y，并且在分支部分 Y 上具有两个活性基团 V2，这两个活性基团与活性基团 V1 进行铃木交叉偶联反应；反应步骤 3：将由此形成的化合物的噻吩环的α位氢转化为发生铃木交叉偶联反应的活性基团 V1，并使化合物（c）与活性基团 V1 反应，从而形成后续的树枝状化合物；以及根据需要重复反应步骤 3，从而形成树枝状聚合物。
• Dendritic polymer and electronic device element employing the polymer
  申请人：Yamahara Motohiro

  公开号：US20060009614A1

  公开（公告）日：2006-01-12

  An object of the invention is to provide a novel dendritic polymer serving as an organic semiconductor material which is isotropic and which exhibits remarkably high carrier conductivity. Another object of the invention is to provide an electronic device employing the dendritic polymer. These objects are attained by a dendritic polymer having a branching structure including repeating units each having a branch portion, each of said repeating units having a structure represented by formula (1), and containing a linear portion X formed of an optionally substituted divalent organic group and a branch portion Y formed of an optionally substituted trivalent organic group: characterized in that the linear portion X contains at least one thienylene moiety and is at least partially conjugated with the branch portion Y, and in that the polymer reversibly assumes an insulative state and a metallic state, depending on the presence of an external factor.

  本发明的一个目的是提供一种新型树枝状聚合物，用作有机半导体材料，这种材料具有各向同性，并表现出极高的载流子传导性。本发明的另一个目的是提供一种采用该树枝状聚合物的电子设备。本发明的上述目的是通过树枝状聚合物来实现的，该树枝状聚合物具有分支结构，包括每个具有分支部分的重复单元，每个所述重复单元具有式（1）表示的结构，并包含由任选取代的二价有机基团形成的线性部分 X 和由任选取代的三价有机基团形成的分支部分 Y：其特征在于，线性部分 X 至少含有一个噻吩基，并至少部分地与支链部分 Y 共轭；聚合物可根据外部因素的存在，可逆地呈现绝缘状态和金属状态。
• Dendrimer and electronic device element employing the same
  申请人：Yamahara Motohiro

  公开号：US20060102890A1

  公开（公告）日：2006-05-18

  An object of the invention is to provide a novel dendrimer serving as an organic semiconductor material which is isotropic and which exhibits remarkably high carrier conductivity. Another object of the invention is to provide an electronic device employing the dendrimer. These objects are attained by a dendrimer having a branching structure in which repeating units each having a branch portion are repeatedly linked through the divergent method or the convergent method, each of said repeating units having a structure represented by formula (1), and containing a linear portion X formed of an optionally substituted divalent organic group and a branch portion Y formed of an optionally substituted trivalent organic group: characterized in that the linear portion X contains at least one thienylene moiety and is at least partially conjugated with the branch portion Y.

  本发明的一个目的是提供一种新型树枝状聚合物作为有机半导体材料，这种材料具有各向同性，并表现出极高的载流子传导性。本发明的另一个目的是提供一种采用该树枝状聚合物的电子装置。本发明的上述目的是通过一种具有分支结构的树枝状聚合物来实现的，在该树枝状聚合物中，每个具有分支部分的重复单元通过发散法或聚合法重复连接，每个所述重复单元具有式（1）表示的结构，并包含由任选取代的二价有机基团形成的线性部分 X 和由任选取代的三价有机基团形成的分支部分 Y：其特征在于，线性部分 X 至少包含一个噻吩分子，并至少与分支部分 Y 部分共轭。
• Process for producing dendrimer, building block compound, and process for producing thiophene compound
  申请人：Obara Satoru

  公开号：US20060122364A1

  公开（公告）日：2006-06-08

  A method for producing a dendrimer having a structural repeating unit which is represented by formula (1) and which contains a linear portion including a thienylene moiety and a branch portion Y formed of an optionally substituted trivalent organic group. The method is based on the convergent method and includes reaction step 1 of converting α-position hydrogen of the thiophene ring of a thienylene-moiety-containing compound (a) for forming end moieties to an active group V 1 which undergoes Suzuki cross-coupling reaction, to thereby form compound (b); reaction step 2 of subjecting a compound (c) to Suzuki cross-coupling reaction with the compound (b), to thereby yield compound (d), the compound (c) having a linear portion and a branch portion Y and having, at the branch portion Y, two active groups V 2 which undergo Suzuki cross-coupling reaction with the active group V 1 ; reaction step 3 of converting α-position hydrogen of the thiophene ring of the thus-formed compound to an active group V 1 which undergoes Suzuki cross-coupling reaction, and reacting the compound (c) with the active group V 1 , to thereby form a dendron of a subsequent generation; and a step of repeating the reaction step 3 in accordance with needs, to thereby form a dendrimer.

  一种生产树枝状聚合物的方法，该树枝状聚合物具有结构重复单元，其结构重复单元由式（1）表示，包含包括噻吩分子的线性部分和由任选取代的三价有机基团形成的分支部分Y。该方法基于聚合法，包括反应步骤 1：将含噻吩基化合物（a）的噻吩环的α位氢转化为活性基团 V，以形成末端分子。 1 反应步骤 2 将化合物 (c) 与化合物 (b) 进行铃木交叉偶联反应，从而得到化合物 (d)，化合物 (c) 具有线性部分和分支部分 Y，并在分支部分 Y 上具有两个活性基团 V 2 与活性基团 V2 发生铃木交叉偶联反应 1 反应步骤 3 将由此形成的化合物中噻吩环的α位氢转化为活性基团 V 1 发生铃木交叉偶联反应，并使化合物 (c) 与活性基团 V 1 与活性基团 V 1 反应，从而形成下一代树枝状化合物；以及根据需要重复反应步骤 3 的步骤，从而形成树枝状聚合物。