5,5''-dichloro-2,2':5',2''-terthiophene | 13669-14-2

• 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: 5,5''-dichloro-2,2':5',2''-terthiophene
• 英文别名: 2,5"-dichloro-2,2',5',2"-terthiophene；H2tth；5,5''-Dichloro-2,2':5',2''-terthiophene；2,5-bis(5-chlorothiophen-2-yl)thiophene
• CAS: 13669-14-2
• 化学式: C₁₂H₆Cl₂S₃
• 分子量: 317.284
• InChiKey: FMVZMHKHEDOCRL-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  403.0±40.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  17
• 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：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5''-dichloro-2,2':5',2''-terthiophene 在 正丁基锂 、 氯化亚砜 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 5,5''-Dichloro-[2,2';5',2'']terthiophene-4,4''-dicarboxylic acid bis-octadecylamide
  参考文献：
  名称：

  Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives

  摘要：

  In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N'-dialkyl-5,5"-dichloro-2,2:5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DCl3T, n=8, 18), N,N"-dialkyl-5,5"-dibromo-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DBr3T, n=5, 8, 16, 18), or N,N'-dialkyl-5,5"-diiodo-2,2:5',2"-terthiophene-4,4"-dica-rboxamide (DNC(n)DI3T, n=8, 18), were designed and synthesized, and their thermal behaviour was examined. It was found that DNC(18)DC13T, DNC(n)DBr3T and DNC(n)DBr3T (n=8, 16, 18) form a smectic A phase and that the alkyl chain length greatly affects liquid crystal phase formation. The absence of liquid crystallinity in the corresponding ester derivatives suggests that intermolecular hydrogen bonding also plays a role in the formation of a liquid crystal phases in the DNC(n)DBr3T system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.029
• 作为产物：
  描述：

  alpha-三联噻吩 在 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 5,5''-dichloro-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives

  摘要：

  In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N'-dialkyl-5,5"-dichloro-2,2:5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DCl3T, n=8, 18), N,N"-dialkyl-5,5"-dibromo-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DBr3T, n=5, 8, 16, 18), or N,N'-dialkyl-5,5"-diiodo-2,2:5',2"-terthiophene-4,4"-dica-rboxamide (DNC(n)DI3T, n=8, 18), were designed and synthesized, and their thermal behaviour was examined. It was found that DNC(18)DC13T, DNC(n)DBr3T and DNC(n)DBr3T (n=8, 16, 18) form a smectic A phase and that the alkyl chain length greatly affects liquid crystal phase formation. The absence of liquid crystallinity in the corresponding ester derivatives suggests that intermolecular hydrogen bonding also plays a role in the formation of a liquid crystal phases in the DNC(n)DBr3T system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.029

文献信息

• Dinuclear palladium–azido complexes containing thiophene derivatives: reactivity toward organic isocyanides and isothiocyanates
  作者：Xiaohong Chang、Mi-Young Kim、Yong-Joo Kim、Hyun Sue Huh、Soon W. Lee

  DOI：10.1039/b616901e

  日期：——

  Cyclopalladated tetranuclear Pd(II) complexes, [Pd2(µ-Cl)2(Y)]2 (Y = L1 or L2; H2L1 = di(2-pyridyl)-2,2′-bithiophene; H2L2 = 5,5″-di(2-pyridyl)-2,2′:5′,2″-terthiophene), containing two pyridyl-α, α′-disubstituted derivatives of thiophene were prepared. Treating these products with PR3 and subsequently with NaN3 produced the dinuclear Pd–azido complexes [(PR3)2(N3)Pd–Y–Pd(N3)(PR3)2] (Y = L1 or L2) or a cyclometallated complex [(PR3)(N3)Pd–Y′–Pd(N3)(PR3)] (Y′ = C,N-L2). Reactions of these Pd–azido complexes with CN–Ar (Ar = 2,6-Me2C6H3, 2,6-i-Pr2C6H3) or R–NCS (R = i-Pr, Et, allyl) led to the complexes containing end-on carbodiimido groups [(PMe3)2(NCN–Ar)Pd–Y–Pd(NCN–Ar)(PMe3)2] or S-coordinated tetrazole-thiolato groups (PMe3)2[CN4(R)]S–Pd–Y–Pd–S[CN4)(R)](PMe3)2}. Interestingly, when treated with elemental sulfur, the carbodiimido complexes transformed into the cyclometallated derivatives, [(PMe3)(NCN–Ar)Pd–Y′–Pd(NCN–Ar)(PMe3)] (Y′ = C,N-L1, C,N-L2). We also report the preparation of linear, thienylene-bridged dinuclear Pd complexes [L2(N3)Pd–X(or X′)–Pd(N3)L2] (L = PMe3 or PMe2Ph; H2X = 2,2′-bithiophene or H2X′ = 2,2′:5′,2″-terthiophene) and their reactivity toward organic isocyanide and isothiocyanates.

  含两个吡啶基-α,α'-二取代噻吩衍生物的环钯化四核铂(II)配合物,[Pd2(μ-Cl)2(Y)]2(Y=L1或L2;H2L1=二(2-吡啶基)-2,2'-联噻吩;H2L2=5,5''-二(2-吡啶基)-2,2':5',2''-三联噻吩)已被合成。将这些产物与PR3反应,随后与NaN3反应,得到双核Pd-叠氮配合物[(PR3)2(N3)Pd-Y-Pd(N3)(PR3)2](Y=L1或L2)或环金属化配合物[(PR3)(N3)Pd-Y'-Pd(N3)(PR3)](Y'=C,N-L2)。这些Pd-叠氮配合物与CN-Ar(Ar=2,6-Me2C6H3,2,6-i-Pr2C6H3)或R-NCS(R=i-Pr,Et,烯丙基)反应,生成含端基卡宾二亚胺[(PMe3)2(NCN-Ar)Pd-Y-Pd(NCN-Ar)(PMe3)2]或硫配位的四唑硫醇盐[(PMe3)2[CN4(R)]S-Pd-Y-Pd-S[CN4)(R)](PMe3)2]的配合物。有趣的是,当与元素硫反应时,卡宾二亚胺配合物转化为环金属化衍生物[(PMe3)(NCN-Ar)Pd-Y'-Pd(NCN-Ar)(PMe3)](Y'=C,N-L1,C,N-L2)。我们还报道了制备线性噻吩桥连双核Pd配合物[L2(N3)Pd-X(或X')-Pd(N3)L2](L=PMe3或PMe2Ph;H2X=2,2'-联噻吩或H2X'=2,2':5',2''-三联噻吩)及其与有机异氰和异硫氰的反应性。
• Rapid and Effective Multihalogenations of 2,2',5',2''-Terthiophene with 2-Halo-4,5-dichloropyridazin-3(2H)-ones under Ambient Conditions
  作者：Eun-Jung Kim、Kwang-Ju Jung、In-Hye Lee、Bo-Ram Kim、Jeum-Jong Kim、Jong-Keun Park、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.5012/bkcs.2010.31.10.2985

  日期：2010.10.20
• Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives
  作者：Ping Liu、Yamin Zhang、Guiju Feng、Jianhua Hu、Xiaoping Zhou、Qizhong Zhao、Yunhua Xu、Zhen Tong、Wenji Deng

  DOI：10.1016/j.tet.2004.04.029

  日期：2004.6

  In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N'-dialkyl-5,5"-dichloro-2,2:5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DCl3T, n=8, 18), N,N"-dialkyl-5,5"-dibromo-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC(n)DBr3T, n=5, 8, 16, 18), or N,N'-dialkyl-5,5"-diiodo-2,2:5',2"-terthiophene-4,4"-dica-rboxamide (DNC(n)DI3T, n=8, 18), were designed and synthesized, and their thermal behaviour was examined. It was found that DNC(18)DC13T, DNC(n)DBr3T and DNC(n)DBr3T (n=8, 16, 18) form a smectic A phase and that the alkyl chain length greatly affects liquid crystal phase formation. The absence of liquid crystallinity in the corresponding ester derivatives suggests that intermolecular hydrogen bonding also plays a role in the formation of a liquid crystal phases in the DNC(n)DBr3T system. (C) 2004 Elsevier Ltd. All rights reserved.