5-(3-thiophen-2-yl-benzo[c]thiophen-1-yl)thiophene-2-carbaldehyde | 205643-85-2

• 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: 5-(3-thiophen-2-yl-benzo[c]thiophen-1-yl)thiophene-2-carbaldehyde
• 英文别名: 5-[3-(thiophen-2-yl)benzo[c]thiophenyl]thiophene-2-carbaldehyde；5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde；1,3-di(2-thienyl)benzo[c]thiophene-5-carbaldehyde；5-(3-Thiophen-2-yl-2-benzothiophen-1-yl)thiophene-2-carbaldehyde
• CAS: 205643-85-2
• 化学式: C₁₇H₁₀OS₃
• 分子量: 326.464
• InChiKey: MHYRMEAQIIYDEV-UHFFFAOYSA-N

物化性质

• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-thiophen-2-yl-benzo[c]thiophen-1-yl)thiophene-2-carbaldehyde 在 正丁基锂 、 四甲基乙二胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1,3-di(2-thienyl)benzo[c]thiophene-5,5'-dicarboxaldehyde
  参考文献：
  名称：

  Studies in the Dithienylbenzo[c]thiophene Series

  摘要：

  A number of derivatives of 1,3-dithienylbenzo[c]thiophene have been synthesized. The mono-and dicarboxaldehydes have been elaborated to give new vinylenes and cyanovinylenes. beta-Dodecyl- and hexyl-substituted analogues have been prepared. Results from cyclic voltammetric investigation as well as fluorescence studies are reported.

  DOI：

  10.1021/jo980246a
• 作为产物：
  描述：

  1,2-di[S-(2-pyridinyl)]benzenedithioate 在 劳森试剂 、 碘 、 magnesium 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(3-thiophen-2-yl-benzo[c]thiophen-1-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  与阳离子 Fe 和 Ru 衍生物相关的苯并 [c] 噻吩发色团用于 NLO 材料：合成表征和二次超极化

  摘要：

  通式为[M(η5-C5H5)(PP)(L1)][PF6]的η5-单环戊二烯基(II)/钌(II)配合物{M = Fe，PP = dppe；M = Ru，PP = dppe 或 2PPh3；L1 = 5-[3-(thiophen-2-yl)benzo[c]thiophenyl]thiophene-2-carbonitrile} 已被合成并研究以评估其分子二次超极化。这些化合物通过 NMR、FTIR 和 UV/Vis 光谱进行了充分表征，并通过循环伏安法研究了它们的电化学行为。二次超极化率 (β) 由超瑞利散射测量在 1500 nm 的基本波长确定。采用密度泛函理论计算来合理化这些复合物的二阶非线性光学特性。

  DOI：

  10.1002/ejic.201300048

文献信息

• Synthesis and photophysical properties of benzo[<i>c</i>]thiophene, <i>p</i>-phenylene-, triphenylamine-, and pyrene-based vinylenes
  作者：Meganathan Nandakumar、Elumalai Sankar、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397911.2016.1228111

  日期：2016.11.16

  ABSTRACT An efficient synthesis of benzo[c]thiophenyl/p-phenylenyl/pyrenyl phosphonate esters has been achieved using ZnBr2-catalyzed Michaelis–Arbuzov reaction of corresponding benzyl alcohol/bromides at room temperature. Horner–Wadsworth–Emmons reaction of the phosphonate esters with aryl/heteroaryl aldehydes in the presence of t-BuOK furnished the vinylenes in good yields. The absorption and emission

  摘要 使用 ZnBr2 催化的相应苯甲醇/溴化物的 Michaelis-Arbuzov 反应在室温下实现了苯并 [c] 噻吩/对苯/芘膦酸酯的有效合成。在 t-BuOK 存在下，膦酸酯与芳基/杂芳基醛的 Horner-Wadsworth-Emmons 反应以良好的收率提供了亚乙烯基。还报道了合成亚乙烯基的吸收和发射特性。图形概要
• Synthesis and Characterization of Benzannelated Thienyl Oligomers
  作者：Pitchamuthu Amaladass、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200800244

  日期：2008.8

  An array of 1,3-diarylbenzo[c]thiophenes have been synthesized by the ring-opening of lactones followed by thionation using Lawesson's reagent with concurrent intramolecular cyclization. Photophysical studies of the various benzo[c]thiophene analogues are presented. The results of a cyclic voltammetric investigation of the benzo[c]thiophenes are also reported.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  一系列 1,3-二芳基苯并 [c] 噻吩已通过内酯的开环合成，然后使用 Lawesson 试剂进行硫化并同时进行分子内环化。介绍了各种苯并 [c] 噻吩类似物的光物理研究。还报告了苯并 [c] 噻吩的循环伏安法研究结果。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Synthesis, spectral, electrochemical and photovoltaic properties of novel heteroleptic polypyridyl ruthenium(II) donor-antenna dyes
  作者：Katja Willinger、Katja Fischer、Roman Kisselev、Mukundan Thelakkat

  DOI：10.1039/b901988j

  日期：——

  A series of new heteroleptic Ru(II)(4,4′-dicarboxylic acid-2,2′-bipyridine)(bipyridyl donor-antenna ligand)(NCS)2 complexes carrying different donor-antenna moieties was designed, synthesised and characterised. A general synthetic procedure was used for the covalent attachment of the donor-antenna units 1,3-di(2-thienyl)benzo[c]-thiophene (DTBT), trans-stilbene (tS) and 4-2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}-N,N-diphenylbenzenamine (TPA-EO) to 2,2′-bipyridine. First, a Vilsmeier-Haack reaction was applied to get the respective aldehyde-functionalised donor-antenna compounds which secondly reacted with 4,4′-bis(triphenylphosphonium-methyl)-2,2′-bipyridyl chloride under Wittig conditions to give the desired bipyridyl donor-antenna molecules. To create a dimethylamino (NMe2) substituted donor-antenna compound a reaction between 4,4′-dimethyl-2,2′-bipyridine and Bredereck's reagent was carried out. The final Ru(II) complexes referred to as Ru-DTBT-NCS, Ru-tS-NCS, Ru-TPA-EO-NCS and Ru-NMe2-NCS were obtained via one-pot reactions, starting from dichloro(p-cymene)ruthenium(II) dimer. The bipyridyl donor-antenna molecules as well as the complexes were fully characterised and their optical and electrochemical properties were studied in detail. Preliminary tests of the novel Ru(II)bis(bipyridyl)(NCS)2 dyes in solid-state dye-sensitized solar cells under AM1.5G conditions (100 mW cm−2) yielded short-circuit current densities of 1.06, 2.15, 3.42 and 4.03 mA cm−2, open-circuit voltages of 625, 635, 685 and 735 mV and fill factors of about 45% corresponding to overall efficiencies of 0.31, 0.58, 0.99 and 1.37% for Ru-DTBT-NCS, Ru-NMe2-NCS, Ru-tS-NCS and Ru-TPA-EO-NCS, respectively.

  我们设计、合成并表征了一系列携带不同供体-天线分子的新型杂环 Ru(II)(4,4′-二羧酸-2,2′-联吡啶)(联吡啶供体-天线配体)(NCS)2 配合物。将 1,3-二（2-噻吩基）苯并[c]-噻吩（DTBT）、反式二苯乙烯（tS）和 4-2-[2-（2-甲氧基乙氧基）乙氧基]-乙氧基}-N,N-二苯基苯胺（TPA-EO）共价连接到 2,2′-联吡啶时，采用了一般的合成程序。首先，通过 Vilsmeier-Haack 反应得到相应的醛官能化的供体天线化合物，然后在 Wittig 条件下与 4,4′-双（三苯基膦-甲基）-2,2′-联吡啶氯反应，得到所需的双吡啶供体天线分子。为了生成二甲基氨基（NMe2）取代的供体天线化合物，4,4′-二甲基-2,2′-联吡啶和布雷德克试剂发生了反应。从二氯（对苯二酚）钌（II）二聚体开始，通过一锅反应最终得到了 Ru（II）配合物，即 Ru-DTBT-NCS、Ru-tS-NCS、Ru-TPA-EO-NCS 和 Ru-NMe2-NCS。对双吡啶供体-天线分子以及配合物进行了全面表征，并详细研究了它们的光学和电化学特性。在 AM1.5G 条件（100 mW cm-2）下，在固态染料敏化太阳能电池中对新型 Ru(II)双(联吡啶)(NCS)2 染料进行了初步测试，短路电流密度分别为 1.06、2.15、3.42 和 4.03 mA cm-2，开路电压分别为 625、635、685 和 735 mV，填充因子约为 45%，Ru-DTBT-NCS、Ru-NMe2-NCS、Ru-tS-NCS 和 Ru-TPA-EO-NCS 的总效率分别为 0.31、0.58、0.99 和 1.37%。
• Synthesis of Benzo[<i>c</i>]thiophene Analogs Containing Benzimidazole, Benzothiazole, and Oxazole
  作者：J. Arul Clement、Pethaiah Gunasekaran、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397910902763912

  日期：2009.8.20

  Iodine-mediated cyclization of benzo[c]thiophene aldehyde with 1,2-diphenylamine/2-aminophenylthiol led to the formation of benzimidazole/benzothiazole-incorporated benzo[c]thiophenes. Similarly, reaction of benzo[c]thiophene aldehyde with p-toluenesulfonylmethyl isocyanide (TOSMIC) reagent in the presence of K2CO3 as a base furnished oxazole-containing benzo[c]thiophene analogs.

  摘要 碘介导的苯并 [c] 噻吩醛与 1,2-二苯胺/2-氨基苯硫醇的环化导致苯并咪唑/苯并噻唑结合的苯并 [c] 噻吩的形成。类似地，苯并 [c] 噻吩醛与对甲苯磺酰基甲基异氰化物 (TOSMIC) 试剂在 K2CO3 作为碱存在下的反应提供了含恶唑的苯并 [c] 噻吩类似物。
• Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.3987/com-14-13145

  日期：——

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.