2,5-二亚甲基-2,5-二氢噻吩 | 66806-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2,5-二亚甲基-2,5-二氢噻吩
• 英文名称: 2,5-Dimethylen-2,5-dihydro-thiophen
• 英文别名: 2,5-Dimethylidenethiophene
• CAS: 66806-34-6
• 化学式: C₆H₆S
• 分子量: 110.18
• InChiKey: BXWYMBNOGOSABW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-二亚甲基-2,5-二氢噻吩 在 lithium aluminium tetrahydride 、 氧气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,5-bis(hydroxymethyl)thiophene
  参考文献：
  名称：

  Reaction of 2,5-dimethylene-2,5-dihydrothiophene with triplet oxygen

  摘要：

  2,5-Dimethylene-2,5-dihydrothiophene (1), prepared by the pyrolysis of 5-methylthenyl benzoate (3), has been detected by low-temperature NMR spectroscopy. 1 reacts with triplet oxygen to form a cyclic bisperoxide 6. Upon heating, 6 decomposes to give 2,5-bis(hydroxymethyl)thiophene (7), 2-formyl-5-hydroxymelhylthiophene (8) and 2,5-diformylthiophene (9) in a ratio of 1:2:1, respectively.

  DOI：

  10.1016/s0040-4039(00)73143-1
• 作为产物：
  描述：

  (5-甲基噻吩-2-基)甲醇 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 600.0 ℃ 、2.67 Pa 条件下， 生成 2,5-二亚甲基-2,5-二氢噻吩
  参考文献：
  名称：

  Detection of 2,5-dimethylene-2,5-dihydrothiophene and thiophenoradialene

  摘要：

  DOI：

  10.1016/s0040-4039(00)82314-x
• 作为试剂：
  描述：

  2,5-dimethylene-2,5-dihydro-furan 在 2,5-二亚甲基-2,5-二氢噻吩 作用下， 生成 [2.2](2.5)furanocyclophane 、 13-oxa-14-thiatricyclo[8.2.1.1^3,6]tetradeca-4,6,10,12-tetraene 、 13,14-二硫杂三环[8.2.1.14,7]十四碳-4,6,10,12-四烯立体异构体混合物 、 19-oxa-20,21-dithiatetracyclo[14.2.1.1^3.6.1^9,12]heneicosa-4,6,10,12,16,18-hexaene
  参考文献：
  名称：

  Oligomerization of the Thiophene-Based p-Quinodimethanes 2,5-Dimethylene-2,5-dihydrothiophene and 2-Ethylidene-5-methylene-2,5-dihydrothiophene

  摘要：

  Flash vacuum pyrolysis (FVP) of (5-methyl-2-thiophene-yl)methyl benzoate (8) produces in ca. 75% yield 2,5-dimethylene-2,3-dihydrothiophene, S-monomer (3). S-Monomer 3 is relatively stable dissolved in carbon disulfide-chloroform at -78 degrees C. The structure of 3 is confirmed by its spectral properties. When a 0.17 M solution of S-monomer 3 was allowed to warm to room temperature, SS-dimer 5 ([2,2](2,5)thiophenophane, 14.7%), SSS-trimer 7 ([2,2,2](2,5)thiophenophane, 44.3%), and polymer were produced. A small amount (<1%) of an SSSS-tetramer was detected by GC/MS. The mechanism proposed for the formation of these oligomers involves the combination of two molecules of 3 to give an intermediate diradical (11) that can close to form dimer 5 or react with additional molecules of 3 to form the higher oligomers. Evidence for the trapping of diradical 11 by 2,5-dimethylene-2,5-dihydrofuran (O-monomer 2) was obtained. Co-oligomerization of S-monomer 3 and O-monomer 2 gave four compounds containing the thiophene moiety: OS-dimer 16, SS-dimer 5, OSS-trimer 17, and SSS-trimer 7. Some OO-dimer 4 was produced but no 000-trimer 6 was observed and only a trace of OOS-trimer 18 was detected. Additional support for the diradical mechanism was obtained from the study of the oligomerization of the methyl derivatives of 3,2-ethylidene-5-methylene-2,5-dihydrothiophene (10, E and Z isomers), prepared by the FVP of (5-ethyl-2-thiophene-yl)methyl benzoate (9). Oligomerization of 10 gave several dimers and trimers including two acyclic dimers that are accounted for by intramolecular disproportionation.

  DOI：

  10.1021/jo961528i

文献信息

• PLANAR CONJUGATED COMPOUNDS AND THEIR APPLICATIONS FOR ORGANIC ELECTRONICS
  申请人：Chen Zhikuan

  公开号：US20110303909A1

  公开（公告）日：2011-12-15

  The invention relates to organic semiconducting materials, methods for their preparation and organic electronic devices incorporating the said organic semiconducting materials. The organic semiconductors contain a compound of formula (I) Ar 1 =(Qu) m =Ar 2 (I) where Qu is independently a substituted or unsubstituted, substantially planar 5 to 8 membered conjugated ring, and Ar 1 and Ar 2 each independently is a substituted or unsubstituted, substantially planar conjugated aromatic structure having from 5 to 50 carbon atoms. The compounds of formula may generally form an H-shaped molecular structure. The said organic semiconducting materials could be used as the active layers for organic electronic devices, e.g. thin film transistors, photovoltaic cells, photo detectors, light emitting diodes, memory cells, sensors etc.

  本发明涉及有机半导体材料、其制备方法以及包含所述有机半导体材料的有机电子器件。所述有机半导体材料包含式(I)的化合物，其中Ar1 = (Qu) m = Ar2(I)，其中Qu是独立的取代或未取代、基本平面的5至8成员共轭环，而Ar1和Ar2各自独立地是具有5至50个碳原子的取代或未取代的基本平面共轭芳香结构。通常，式(I)的化合物可形成H形分子结构。所述有机半导体材料可用作有机电子器件的活性层，例如薄膜晶体管、光伏电池、光探测器、发光二极管、存储器件、传感器等。
• Detection of 2,5-dimethylene-2,5-dihydrothiophene and thiophenoradialene
  作者：Norbert Münzel、Karl Kesper、Armin Schweig、Harald Specht

  DOI：10.1016/s0040-4039(00)82314-x

  日期：1988.1
• Huang Chin-Shui, Peng Chun-Chieh, Chou Chin-Hsing, Tetrahedron Lett, 35 (1994) N 24, S 4175-4176
  作者：Huang Chin-Shui, Peng Chun-Chieh, Chou Chin-Hsing

  DOI：——

  日期：——
• Oligomerization of the Thiophene-Based <i>p</i>-Quinodimethanes 2,5-Dimethylene-2,5-dihydrothiophene and 2-Ethylidene-5-methylene-2,5-dihydrothiophene
  作者：Walter S. Trahanovsky、Deborah Louise Miller、Yili Wang

  DOI：10.1021/jo961528i

  日期：1997.12.1

  Flash vacuum pyrolysis (FVP) of (5-methyl-2-thiophene-yl)methyl benzoate (8) produces in ca. 75% yield 2,5-dimethylene-2,3-dihydrothiophene, S-monomer (3). S-Monomer 3 is relatively stable dissolved in carbon disulfide-chloroform at -78 degrees C. The structure of 3 is confirmed by its spectral properties. When a 0.17 M solution of S-monomer 3 was allowed to warm to room temperature, SS-dimer 5 ([2,2](2,5)thiophenophane, 14.7%), SSS-trimer 7 ([2,2,2](2,5)thiophenophane, 44.3%), and polymer were produced. A small amount (<1%) of an SSSS-tetramer was detected by GC/MS. The mechanism proposed for the formation of these oligomers involves the combination of two molecules of 3 to give an intermediate diradical (11) that can close to form dimer 5 or react with additional molecules of 3 to form the higher oligomers. Evidence for the trapping of diradical 11 by 2,5-dimethylene-2,5-dihydrofuran (O-monomer 2) was obtained. Co-oligomerization of S-monomer 3 and O-monomer 2 gave four compounds containing the thiophene moiety: OS-dimer 16, SS-dimer 5, OSS-trimer 17, and SSS-trimer 7. Some OO-dimer 4 was produced but no 000-trimer 6 was observed and only a trace of OOS-trimer 18 was detected. Additional support for the diradical mechanism was obtained from the study of the oligomerization of the methyl derivatives of 3,2-ethylidene-5-methylene-2,5-dihydrothiophene (10, E and Z isomers), prepared by the FVP of (5-ethyl-2-thiophene-yl)methyl benzoate (9). Oligomerization of 10 gave several dimers and trimers including two acyclic dimers that are accounted for by intramolecular disproportionation.
• Reaction of 2,5-dimethylene-2,5-dihydrothiophene with triplet oxygen
  作者：Chin-Shui Huang、Chun-Chieh Peng、Chin-Hsing Chou

  DOI：10.1016/s0040-4039(00)73143-1

  日期：1994.6

  2,5-Dimethylene-2,5-dihydrothiophene (1), prepared by the pyrolysis of 5-methylthenyl benzoate (3), has been detected by low-temperature NMR spectroscopy. 1 reacts with triplet oxygen to form a cyclic bisperoxide 6. Upon heating, 6 decomposes to give 2,5-bis(hydroxymethyl)thiophene (7), 2-formyl-5-hydroxymelhylthiophene (8) and 2,5-diformylthiophene (9) in a ratio of 1:2:1, respectively.