4,4'-bis(benzo[c][1,2,5]thiadiazole) | 221540-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,4'-bis(benzo[c][1,2,5]thiadiazole)
• 英文别名: 4,4'-bis(2,1,3-benzothiadiazole)；4-(2,1,3-Benzothiadiazol-4-yl)-2,1,3-benzothiadiazole
• CAS: 221540-54-1
• 化学式: C₁₂H₆N₄S₂
• 分子量: 270.338
• InChiKey: FQEDIRZORPHCBS-UHFFFAOYSA-N

物化性质

• 沸点：
  448.1±20.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-bis(benzo[c][1,2,5]thiadiazole) 在 硫酸 、 碘 、 silver sulfate 作用下， 以85%的产率得到7,7'-diiodo-4,4'-bi(2,1,3-benzothiadiazole)
  参考文献：
  名称：

  第一种稳定的具有完全平面几何形状的稳定的四氰基二苯并喹啉二甲烷：双[1,2,5]噻二唑-TCNDQ的制备，X射线结构和高导电络合物

  摘要：

  新设计并制备了标题为四氰基二苯并醌二甲烷（TCNDQ）的衍生物，作为高导电性有机材料的新型组分。将1,2,5-噻二唑环引入TCNDQ骨架可在中性状态下实现较大的稳定性。X射线分析揭示了它们的结构细节，这表明原子间相互作用（CH…N，S…N）在确定分子和晶体结构中起着重要作用。新型电子受体显示出与TCNQ相当的强大电子亲和力，并产生了高导电性的电荷转移（CT）络合物和阴离子自由基盐。

  DOI：

  10.1016/s0040-4039(98)02557-x
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 四丁基溴化铵 、 氢溴酸 、 溴 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 生成 4,4'-bis(benzo[c][1,2,5]thiadiazole)
  参考文献：
  名称：

  探索共轭材料中供体-受体效应的性质：模型共轭低聚物的联合实验和计算研究

  摘要：

  一系列由传统强供体单元（3,4-亚乙基二氧噻吩）、传统强受体单元（苯并[ c ][1,2,5]噻二唑）和双极性单元噻吩并[3, 4- b ]吡嗪通过交叉偶联方法合成。制备的低聚物包括所有六种可能的二聚体组合，以表征共轭材料设计中常用的供体-受体效应的程度和性质，特别关注了解包含双极单元如何影响供体-受体框架。完整的低聚物系列通过光物理和电化学研究，与密度泛函理论 (DFT) 计算并行，以便将供体 - 受体效应对前线轨道能量和所需的 HOMO-LUMO 能隙缩小的性质和程度相关联。所揭示的对应关系应该可以更深入地了解供体 - 受体相互作用及其在共轭材料中的应用。

  DOI：

  10.1039/d1cp04603a

文献信息

• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。
• First stable tetracyanodiphenoquinodimethane with a completely planar geometry: Preparation, X-ray structure, and highly conductive complexes of bis[1,2,5]thiadiazolo-TCNDQ
  作者：Takanori Fukushima、Nobuharu Okazeri、Tsutomu Miyashi、Kazuharu Suzuki、Yoshiro Yamashita、Takanori Suzuki

  DOI：10.1016/s0040-4039(98)02557-x

  日期：1999.2

  large stabilization in the neutral state. X-ray analysis has revealed their structural details which suggest that interatomic interactions (CH…N, S…N) play an important role in determining the molecular and crystal structure. The novel electron acceptor shows strong electron affinity comparable with that of TCNQ, and gave highly conductive charge-transfer (CT) complexes and an anion radical salt.

  新设计并制备了标题为四氰基二苯并醌二甲烷（TCNDQ）的衍生物，作为高导电性有机材料的新型组分。将1,2,5-噻二唑环引入TCNDQ骨架可在中性状态下实现较大的稳定性。X射线分析揭示了它们的结构细节，这表明原子间相互作用（CH…N，S…N）在确定分子和晶体结构中起着重要作用。新型电子受体显示出与TCNQ相当的强大电子亲和力，并产生了高导电性的电荷转移（CT）络合物和阴离子自由基盐。
• 방향족융합고리 화합물 및 이를 이용한 유기 태양전지
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR101562426B1

  公开（公告）日：2015-10-22

  본 발명은 방향족융합고리 화합물 및 상기 방향족융합고리 화합물을 광활성층에 포함하는 유기 태양전지를 제공한다.

  该发明提供了一种有机太阳能电池，其中包含方向环融合环化合物和上述方向环融合环化合物在光敏层中。
• BIPYRIDINE COMPOUND, TRANSITION METAL COMPLEX, AND METHOD FOR PRODUCTION OF CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20100184978A1

  公开（公告）日：2010-07-22

  A bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 each independently represent a C1-C10 alkyl group which may be substituted etc., and R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom etc., a transition metal complex obtained by contacting a bipyridine compound represented by the formula (1) with a compound of a transition metal belonging to Group 9, 10 or 11, and a method for production of a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of the transition metal complex.

  一种以式(1)表示的联吡啶化合物：其中R1、R2和R3各自独立地表示可以被取代的C1-C10烷基等，而R4、R5、R6、R7和R8各自独立地表示氢原子等，通过将式(1)表示的联吡啶化合物与属于9、10或11族过渡金属的化合物接触而获得的过渡金属配合物，以及一种制备共轭芳香化合物的方法，包括在过渡金属配合物的存在下，将一个或两个离去基团与芳环结合的芳香化合物（A）与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或结构不同于上述芳香化合物（A）且具有一个或两个离去基团与芳环结合的芳香化合物（B）反应。
• TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20110046336A1

  公开（公告）日：2011-02-24

  A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 represent a C1-C10 alkyl group which may be substituted, etc., and R 4 and R 5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.

  通过将式（1）所表示的联吡啶化合物与属于9、10或11族的过渡金属化合物接触而获得的过渡金属配合物，其中R1、R2和R3代表C1-C10烷基，可以被取代等，而R4和R5代表氢原子等。制备共轭芳香化合物的方法包括，在所述过渡金属配合物的存在下，将一个芳香化合物（A），其中一个或两个离去基团与芳香环相键合，与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或在结构上不同于上述芳香化合物（A）并且具有一个或两个离去基团与芳香环相键合的芳香化合物（B）反应。