12,13-dihydroindolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazole | 1190305-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 12,13-dihydroindolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazole
• 英文别名: thiadiazoleindolo[3,2-b]carbazole
• CAS: 1190305-35-1
• 化学式: C₁₈H₁₀N₄S
• 分子量: 314.37
• InChiKey: RDRLTRJWUKYYLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  12,13-dihydroindolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazole 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 mineral oil 为溶剂， 反应 26.0h， 生成 3,9-dibromo-12,13-dioctyl-12,13-dihydroindolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazole
  参考文献：
  名称：

  Synthesis and structure study of copolymers from thiadiazole fused indolocarbazole and dithienosilole

  摘要：

  We report synthesis and characterization of two D-A polymers (PSDT-C12 and PSDT-EH) with different side chains. Both polymers are based on alternate 12,13-dioctyl-indolo[2,3-a][1,2,5]thiadiazolo[3,4-c] carbazole (TDZIC) and dithienosilole derivative units in polymer main chain. We used TDZIC to enlarge the 2D conjugated plane of acceptor monomers by fusing benzothiadiazole (BT) unit with an indole unit having alkyl groups. PSDT-C12 exhibited 10 nm redshift compared to PSDT-EH in solid films, while their absorption spectra were almost identical in solutions. Since the backbone and side chains on the indolocarbazole group are the same, the redshift on PSDT-C12 could be resulted from the dodecyl (C12) side chain on the dithienosilole unit and different molecular weight between these two polymers. PSDT-C12 has a larger molecular weight than PSDT-EH. Therefore possibly both side chains and molecular weight contributed to the difference in the absorption spectra in solid films. The straight C-12 side chain has less steric hindrance than the branched EH side chain in solid films. PSDT-C12 has a longer main chain (larger molecule weight) than PSDT-EH, which can favour a more extended main chain interaction. The vibronic peak at 519 nm and shoulder at 563 nm in the PSDT-C12 film further confirmed stronger main chain interaction. Geometry optimization showed that head-tail (HT)-PSDT had a more twisting conjugated backbone with larger dihedral angle between dithienosilole unit and thiadiazole-fused ring compared to head-head/tail-tail (HH/TT)-PSDT. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.11.006
• 作为产物：
  描述：

  三丁基苯基锡 在 四(三苯基膦)钯 、 三苯基膦 作用下， 以 邻二氯苯 、 甲苯 为溶剂， 生成 12,13-dihydroindolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazole
  参考文献：
  名称：

  硫族二唑稠合的吲哚[2,3- a ]咔唑中硫族元素原子变化的影响†

  摘要：

  制备了一系列硫族二唑稠合的吲哚[2，3- a ]咔唑1-3，其中硫族原子在硫族二唑单元中从氧（O）到硫（S）到硒（Se）变化。Cadogan闭环反应被用作制备1-3的关键合成步骤。硫族元素的变化（O，S和Se）导致1-3的结构，光学和电化学性质发生了显着变化，表明其HOMO-LUMO能级随后发生了变化。进行密度泛函理论（DFT）计算以进一步支持实验观察到的趋势。

  DOI：

  10.1039/c7nj04661h

文献信息

• 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
  申请人：Solus Advanced Materials co., Ltd. 솔루스첨단소재 주식회사(120190660630) Corp. No ▼ 214911-0058927BRN ▼668-81-01406

  公开号：KR20180071882A

  公开（公告）日：2018-06-28

  본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광 효율, 구동 전압, 수명 등을 향상시킬 수 있다.

  本发明涉及一种新化合物及其在有机电致发光器件中的应用，根据本发明的化合物可用于有机电致发光器件的有机层，特别是用于发光层，可提高有机电致发光器件的发光效率、驱动电压、寿命等。
• π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties
  作者：Shin-ichiro Kato、Takayuki Furuya、Atsushi Kobayashi、Masashi Nitani、Yutaka Ie、Yoshio Aso、Toshitada Yoshihara、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo301458m

  日期：2012.9.7

  We report the syntheses, structures, photophysical properties, and redox characteristics of donor–acceptor-fused π-systems, namely π-extended thiadiazoles 1–5 fused with thienopyrrole or indole moieties. They were synthesized by the Stille coupling reactions followed by the PPh3-mediated reductive cyclizations as key steps. X-Ray crystallographic studies showed that isomeric 1b and 2b form significantly

  我们报告的合成，结构，光物理性质，和供体-受体-稠合的π系统，即π扩展噻二唑的氧化还原特性1 - 5与噻吩并吡咯或吲哚基团稠合的。它们是通过Stille偶联反应，随后是PPh 3介导的还原环化作为关键步骤合成的。X射线晶体学研究表明，异构体1b和2b彼此形成明显不同的堆积，而1a和4a通过与水分子的多个氢键结合形成超分子网络。噻吩并吡咯稠合的化合物1b和2b红移显示移位的分子内电荷转移（CT）频带和低的氧化电位相对于吲哚稠合类似物如图3b和显示中等至良好的荧光量子产率（Φ ˚F）高达0.73。在3b – 5b中，在吲哚基团中引入供电子性取代基显着地红移了分子内CT吸收最大值，并导致HOMO水平升高。的Φ ˚F的值3 - 5被发现（0.04-0.50）是显著依赖于吲哚基团的取代基。1b和2b的OFET属性 还公开了作为活性层的薄膜。
• Donor–Acceptor-Type Semiconducting Polymers Consisting of Benzothiadiazole Derivatives as Electron-Acceptor Units for Organic Photovoltaic Cells
  作者：Hee Su Kim、Jong Baek Park、Ji-Hoon Kim、Do-Hoon Hwang

  DOI：10.1166/jnn.2015.11530

  日期：2015.11.1

  We synthesized two fused pentacyclic donor-acceptor structures, where the two different outer electron rich thiophene (DTPBT) and electron poor benzene (ICTh) moieties are covalently bonded to the central electron-deficient benzothiadiazole core by two nitrogen bridges. These new electron-acceptor DTPBT and ICTh building blocks were copolymerized with fluorene, as the electron donor group, via Suzuki coupling polymerization, to produce two new alternating copolymers, PFDTPBT and PFICTh, respectively. The average molecular weights of the synthesized polymers were determined by GPC. The number-average molecular weights of PFDTPBT and PFICTh were 19,000 (PDI=2.5) and 20,000 (PDI=4.0), respectively. The optical bandgap energies of the polymers were measured from their absorption onsets to be 2.15 and 2.55 eV, depending on the polymer structure. The HOMO energy levels of the polymers were determined, by measuring the oxidation onsets of the polymer films by cyclic voltammetry. The measured HOMO energy levels of PFDTPBT and PFICTh were –5.10 and –5.57 eV, respectively. When the polymers were blended with PC71BM, as the active layer for bulk-heterojunction photovoltaic devices, power conversion efficiencies were 2.08% and 0.34%, respectively, under AM 1.5 G (100 mW cm–2) conditions.

  我们合成了两种融合的五环供体-受体结构，其中两种不同的外部富电子噻唑（DTPBT）和贫电子苯（ICTh）单元通过两个氮桥以共价方式连接到中心贫电子的苯并噻二唑核心。这些新的电子受体DTPBT和ICTh构件与氟烯作为电子供体组分通过铃木偶联聚合反应共聚合，分别生成两种新的交替共聚物PFDTPBT和PFICTh。合成聚合物的平均分子量通过凝胶渗透色谱（GPC）测定。PFDTPBT和PFICTh的数均分子量分别为19,000（PDI=2.5）和20,000（PDI=4.0）。聚合物的光学带隙能量通过其吸收起始点测得，分别为2.15和2.55 eV，具体取决于聚合物结构。聚合物的HOMO能量水平通过循环伏安法测量聚合物薄膜的氧化起始点来确定。PFDTPBT和PFICTh的测得HOMO能量水平分别为–5.10 eV和–5.57 eV。当聚合物与PC71BM混合时，作为大块异质结光伏器件的活性层，在AM 1.5 G（100 mW cm–2）条件下的功率转换效率分别为2.08%和0.34%。
• Thiadiazole Fused Indolo[2,3-<i>a</i>]carbazole Based Oligomers and Polymer
  作者：Ganapathy Balaji、Wong Low Shim、Manoj Parameswaran、Suresh Valiyaveettil

  DOI：10.1021/ol901806q

  日期：2009.10.1

  Indolo[2,3-a]carbazole-based heteroacenes containing thiadiazole units were synthesized. Compounds showed a sandwich herringbone packing in solid state with improved stability. The change in photophysical and electrochemical properties upon incorporation of an acceptor moiety (benzothiadazole) in a fused ring system was studied, The unsubstituted compound was electropolymerized to yield a stable polymer.
• Effects of chalcogen atom variation in chalcogenadiazole fused indolo[2,3-<i>a</i>]carbazoles
  作者：Sirina Ghosh、Neha Rani Kumar、Sanjio S. Zade

  DOI：10.1039/c7nj04661h

  日期：——

  chalcogenadiazole fused indolo[2,3-a]carbazoles 1–3 were prepared, wherein a chalcogen atom was varied from oxygen (O) to sulphur (S) to selenium (Se) in the chalcogenadiazole unit. A Cadogan ring closing reaction was used as the key synthetic step for the preparation of 1–3. The chalcogen alteration (O, S and Se) led to a significant change in the structural, optical and electrochemical properties of 1–3, indicating

  制备了一系列硫族二唑稠合的吲哚[2，3- a ]咔唑1-3，其中硫族原子在硫族二唑单元中从氧（O）到硫（S）到硒（Se）变化。Cadogan闭环反应被用作制备1-3的关键合成步骤。硫族元素的变化（O，S和Se）导致1-3的结构，光学和电化学性质发生了显着变化，表明其HOMO-LUMO能级随后发生了变化。进行密度泛函理论（DFT）计算以进一步支持实验观察到的趋势。