benzo[1,2-b:4,3-b']dithiophene-2-carbaldehyde | 30689-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: benzo[1,2-b:4,3-b']dithiophene-2-carbaldehyde
• 英文别名: benzo[1,2-b;4,3-b']dithiophen-2-carbaldehyde；thieno[3,2-e]benzothiophen-2-carbaldehyde；benzo[1,2-b;4,3-b']dithiophene；2-formyl-benzo[1,2-b;4,3-b']dithiophene；Benzo<1,2-b:4,3-b'>dithiophen-2-carboxaldehyd；Thieno[3,2-e][1]benzothiole-2-carbaldehyde
• CAS: 30689-46-4
• 化学式: C₁₁H₆OS₂
• 分子量: 218.3
• InChiKey: WOAGVIMXXKQBAH-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: methanol (67-56-1))
• 沸点：
  417.2±25.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[1,2-b:4,3-b']dithiophene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 Benzo[1,2-b;4,3-b']dithiophen-2-yl-methanol
  参考文献：
  名称：

  Photochemical synthesis and structural properties of high membered thiohelicenes

  摘要：

  讨论了一种普遍的光化学合成九环和十一环的大硫螺旋烃的方法，以及在晶体中外消旋硫螺旋烃的组装：异旋组装是主要过程，除了在九环系统中，在该系统中，涉及端环硫原子的相互作用有利于在平面中隔离紧密堆积的同旋分子。

  DOI：

  10.1039/b002581j
• 作为产物：
  描述：

  benzo[1,2-b;4,3-b']dithiophene 、 N,N-二甲基甲酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 以72%的产率得到benzo[1,2-b:4,3-b']dithiophene-2-carbaldehyde
  参考文献：
  名称：

  A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective α-functionalisation of terminal thiophene ring

  摘要：

  This paper describes a convenient preparation of tetrathia-[7]-helicene (TH[7]), the generation of the alpha-anion on the terminal thiophene ring, and the synthesis of the 2-formyl-tetrathia-[7]-helicene (2-CHO-TH[7]). The key intermediate trans-1,2-dibenzodithiopheneethene, prepared in 97% yield by McMurry coupling of the 2-formyl-benzo[1,2-b;4,3-b']dithiophene, was transformed into TH[7] using a known procedure. The described method affords TH[7] in 46% overall yield, which is more than four times the yield previously reported in the literature. The alpha-anion of TH[7], which is easily generated on the alpha-position of one of the terminal thiophene rings, reacts with electrophilic reagents such as D2O and DMF. The latter reaction proved to be the best way to prepare 2-CHO-TH[7], a key intermediate for the preparation of new substituted heterohelicenes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01056-1

文献信息

• Silyl-Substituted Tetrathia[7]helicenes: Synthesis, X-ray Characterization and Reactivity
  作者：Alberto Bossi、Stefano Maiorana、Claudia Graiff、Antonio Tiripicchio、Emanuela Licandro

  DOI：10.1002/ejoc.200700494

  日期：2007.9

  We describe the synthesis of trialkylsilyl-substituted trans-1,2-bis(thieno[3,2-e]benzothiophene-2-yl)ethenes as suitable soluble precursors for the preparation of the corresponding silylated tetrathia[7]helicenes, which, in turn, can be desilylated or transformed into dihalogen-substituted derivatives through electrophilic substitution of silyl substituents. X-ray structural studies showed that the

  我们描述了三烷基甲硅烷基取代的反式-1,2-双（噻吩并[3,2-e]苯并噻吩-2-基）乙烯作为制备相应的甲硅烷基化四硫杂[7]螺旋烯的合适可溶性前体的合成，其中，反过来，可以通过甲硅烷基取代基的亲电取代脱甲硅烷基化或转化为二卤代衍生物。X 射线结构研究表明，末端噻吩环上两个三异丙基甲硅烷基的存在是烯烃的高溶解度和螺旋烯中非常大的二面角的原因。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of organometallic Ru(II) and Fe(II) complexes containing fused rings hemi-helical ligands as chromophores. Evaluation of non-linear optical properties by HRS
  作者：M. Helena Garcia、Pedro Florindo、M. Fátima M. Piedade、M. Teresa Duarte、M. Paula Robalo、Jürgen Heck、Christian Wittenburg、Jan Holtmann、Emanuela Licandro

  DOI：10.1016/j.jorganchem.2008.05.035

  日期：2008.9

  and UV–Vis. spectroscopies and their electrochemistry studied by cyclic voltammetry. The X-ray structures of [Ru(η5-C5H5)(PPh3)2(NCC10H5S2)][PF6] (1Ru), [Ru(η5-C5H5)(PPh3)2(NCC10H5S2)][CF3SO3] (1′Ru), [Ru(η5-C5H5)(DPPE)(NCC10H5S2)][PF6] 2Ru and [Fe(η5-C5H5)(DPPE)(NCC10H5S2)][PF6] (2Fe) were determined by X-ray diffraction showing centric crystallization on groups P1¯ and P21/n, respectively.

  三脚钢琴凳的新家族结构的含η片段有机金属化合物5 -环戊二烯基-钌（II）/铁（II）已被合成后的新的苯并二噻吩配体的配位，以评估电子金属与配体的电荷转移的存在（BDT），苯并[1,2- b ; 4,3 - b ']二噻吩-2-甲腈（L1）和苯并[1,2- b ; 4,3 - b ']二噻吩-2'nitro-2 -乙腈（L2）。所有化合物的特征在于1 H，13 C，31P NMR，IR和UV-Vis。循环伏安法研究光谱学及其电化学。的X射线结构的[Ru（η 5 -C 5 H ^ 5）（PPH 3）2（NCC 10 ħ 5小号2）] [PF 6 ]（1RU），的[Ru（η 5 -C 5 H ^ 5） （PPH 3）2（NCC 10 ħ 5小号2）] [CF 3 SO 3 ]（1 '的Ru），的[Ru（η 5 -C 5 H ^5）（DPPE）（NCC 10 ħ 5小号2）] [PF 6 ] 2RU和的[Fe（η
• Ortho-Fused Heterocyclic Derivatives as Efficient Electroluminescent Materials
  作者：Kazuhiko Tanaka、Hideji Osuga、Naoki Tsujiuchi、Masashi Hisamoto、Yuichi Sakaki

  DOI：10.1246/bcsj.75.551

  日期：2002.3

  We describe the synthesis and optical properties of 1,2-dithienylethylene derivatives (DTE-8–15) consisting of ortho-fused heterocyclic systems such as benzodithiophene and naphthothiophene. The compounds 8–13 are highly fluorescent in toluene solution and their intensities are approximately two times as large as 4,4′-bis(2,2-diphenylethenyl)biphenyl (18). The fluorescence quantum yields of compounds 8–15, except for 14, are 2 times as high as that of 18. Although a maximum luminance of 9 in a multilayer device of structure ITO/CuPc/NPD/9/Alq3/LiF/Al is low (186 cd m-2), the brightness is significantly improved by doping the host emitters such as 18 and 9,10-bis(2-biphenylyl)-2-(t-butyl)anthracene (19) with 9. The electroluminescent (EL) device doped with 8 (5%) in the layer of 19 exhibits blue emission with a maximum luminance of 30000 cd m-2 at a driving voltage of 14 V and a luminous efficiency of 2.42 lm W-1 at 5V.

  我们描述了由苯并二噻吩和萘并噻吩等正交融合杂环系统组成的 1,2-二噻吩乙烯衍生物（DTE-8-15）的合成和光学特性。化合物 8-13 在甲苯溶液中具有高荧光，其强度约为 4,4′-双（2,2-二苯基乙烯基）联苯（18）的两倍。除 14 号化合物外，8-15 号化合物的荧光量子产率是 18 号化合物的 2 倍。虽然 9 在 ITO/CuPc/NPD/9/Alq3/LiF/Al 结构的多层器件中的最大亮度较低（186 cd m-2），但通过在 18 和 9,10-双（2-联苯基）-2-（叔丁基）蒽（19）等主发射体中掺杂 9，亮度会显著提高。在 19 层中掺入 8（5%）的电致发光（EL）器件在 14 V 的驱动电压下发出蓝色光，最大亮度为 30000 cd m-2，在 5V 电压下的发光效率为 2.42 lm W-1。
• A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective α-functionalisation of terminal thiophene ring
  作者：Stefano Maiorana、Antonio Papagni、Emanuela Licandro、Rita Annunziata、Piero Paravidino、Dario Perdicchia、Clelia Giannini、Marco Bencini、Koen Clays、André Persoons

  DOI：10.1016/s0040-4020(03)01056-1

  日期：2003.8

  This paper describes a convenient preparation of tetrathia-[7]-helicene (TH[7]), the generation of the alpha-anion on the terminal thiophene ring, and the synthesis of the 2-formyl-tetrathia-[7]-helicene (2-CHO-TH[7]). The key intermediate trans-1,2-dibenzodithiopheneethene, prepared in 97% yield by McMurry coupling of the 2-formyl-benzo[1,2-b;4,3-b']dithiophene, was transformed into TH[7] using a known procedure. The described method affords TH[7] in 46% overall yield, which is more than four times the yield previously reported in the literature. The alpha-anion of TH[7], which is easily generated on the alpha-position of one of the terminal thiophene rings, reacts with electrophilic reagents such as D2O and DMF. The latter reaction proved to be the best way to prepare 2-CHO-TH[7], a key intermediate for the preparation of new substituted heterohelicenes. (C) 2003 Elsevier Ltd. All rights reserved.
• Photochemical synthesis and structural properties of high membered thiohelicenes
  作者：Tullio Caronna、Roberta Sinisi、Luciana Malpezzi、Stefano V. Meille、Andrea Mele、Marinella Catellani

  DOI：10.1039/b002581j

  日期：——

  A general photochemical synthesis of large thiohelicenes containing nine and eleven rings is discussed along with the organisation of racemic thiohelicenes in crystals: heterochiral assembling is dominant except in the nine-ring system where interactions involving terminal ring S atoms favour the segregation of close-packed homochiral molecules in planes.

  讨论了一种普遍的光化学合成九环和十一环的大硫螺旋烃的方法，以及在晶体中外消旋硫螺旋烃的组装：异旋组装是主要过程，除了在九环系统中，在该系统中，涉及端环硫原子的相互作用有利于在平面中隔离紧密堆积的同旋分子。