tert-butyl thiophene-3-carboxylate | 125294-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: tert-butyl thiophene-3-carboxylate
• 英文别名: t-butyl 3-thienoate
• CAS: 125294-45-3
• 化学式: C₉H₁₂O₂S
• 分子量: 184.259
• InChiKey: YPPDPANYMIUZJG-UHFFFAOYSA-N

物化性质

• 沸点：
  235.9±13.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl thiophene-3-carboxylate 在 N-碘代丁二酰亚胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 氯仿 、 溶剂黄146 为溶剂， 生成 di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(5-iodothiophene-3-carboxylate)
  参考文献：
  名称：

  Low-Bandgap Donor−Acceptor Conjugated Polymer Sensitizers for Dye-Sensitized Solar Cells

  摘要：

  A set of two donor acceptor-type conjugated polymers with carboxylic acid side groups have been synthesized and utilized as active materials for dye-sensitized solar cells (DSSCs). The polymers feature a pi-conjugated backbone consisting of an electron-poor 2,1,3-benzothiadiazole (BTD, acceptor) unit, alternating with either a thiophene-fluorene-thiophene triad (2a) or a terthiophene (3a) segment as the donor. The donor-acceptor polymers absorb broadly throughout the visible region, with terthiophene-BTD polymer 3a exhibiting an absorption onset at approximately 625 nm corresponding to a similar to 1.9 eV bandgap. The polymers adsorb onto the surface of nanostructured TiO2 due to interaction of the polar carboxylic acid units with the metal oxide surface. The resulting films absorb visible light strongly, and their spectra approximately mirror the polymers' solution absorption. Interestingly, a series of samples of 3a with different molecular weight (M-n) adsorb to TiO2 to an extent that varies inversely with M-n. DSSCs that utilize the donor acceptor polymers as sensitizers were tested using an I-/I-3(-) electrolyte. Importantly, for the set of polymer sensitizers 3a with varying M, the DSSC efficiency varies inversely with NI, a result that reflects the difference in adsorption efficiency observed in the film absorption experiments. The best DSSC cell tested is based on a sample of 3a with M-n similar to 4000, and it exhibits a similar to 65% peak IPCE with J(sc) similar to 12.6 mA cm-2 under AM 1.5 illumination and an overall power conversion efficiency of similar to 3%.

  DOI：

  10.1021/ja109926k
• 作为产物：
  描述：

  3-噻吩甲酰氯 、 sodium t-butanolate 反应 3.0h， 以72%的产率得到tert-butyl thiophene-3-carboxylate
  参考文献：
  名称：

  Gas-phase pyrolytic reactions. part 3. Hammett ϱ constants of gas-phase eliminations of alkyl arylcarboxylate and ethanoate esters and their correlation with substrate molecular framework

  摘要：

  DOI：

  10.1016/s0040-4020(01)88382-4

文献信息

• Lewis Acids as Highly Efficient Catalysts for the Decarboxylative Esterification of Carboxylic Acids with Dialkyl Dicarbonates
  作者：L. Gooßen、A. Döhring

  DOI：10.1002/adsc.200303040

  日期：2003.8

  Mild Lewis acids such as Mg(ClO4)2 show a new level of catalytic activity for the decarboxylative esterification of carboxylic acids with commercially available dialkyl dicarbonates. In the presence of as little as one mol % Mg(ClO4)2 catalyst, carboxylic acids can thus easily and near quantitatively be protected at room temperature, e.g., as methyl, benzyl, or t-butyl esters. Only volatile by-products

  温和的路易斯酸（例如Mg（ClO 4）2）对羧酸与可商购的二烷基二碳酸酯的脱羧酯化反应显示出新的催化活性水平。因此，在少至1mol％的Mg（ClO 4）2催化剂的存在下，羧酸可以在室温下容易地和接近定量地被保护，例如，甲基，苄基或叔丁基酯。仅释放挥发性副产物，因此产物的纯化特别容易。容许许多敏感功能，甚至包括酚酯或游离的羟基和BOC基团。
• Gas-phase replacement σ0 substituent constants of heteroaryl groups1
  作者：Nouria A. Al-Awadi、Rasha F. Al-Bashir、Osman M.E. ElDusouqui

  DOI：10.1016/s0040-4039(00)99558-3

  日期：1989.1
• Gas-phase pyrolytic reactions. part 3. Hammett ϱ constants of gas-phase eliminations of alkyl arylcarboxylate and ethanoate esters and their correlation with substrate molecular framework
  作者：Nouria A. Al-Awadi、Rasha F. Al-Bashir、Osman M.E. ElDusouqui

  DOI：10.1016/s0040-4020(01)88382-4

  日期：1990.1
• Low-Bandgap Donor−Acceptor Conjugated Polymer Sensitizers for Dye-Sensitized Solar Cells
  作者：Zhen Fang、Aaron A. Eshbaugh、Kirk S. Schanze

  DOI：10.1021/ja109926k

  日期：2011.3.9

  A set of two donor acceptor-type conjugated polymers with carboxylic acid side groups have been synthesized and utilized as active materials for dye-sensitized solar cells (DSSCs). The polymers feature a pi-conjugated backbone consisting of an electron-poor 2,1,3-benzothiadiazole (BTD, acceptor) unit, alternating with either a thiophene-fluorene-thiophene triad (2a) or a terthiophene (3a) segment as the donor. The donor-acceptor polymers absorb broadly throughout the visible region, with terthiophene-BTD polymer 3a exhibiting an absorption onset at approximately 625 nm corresponding to a similar to 1.9 eV bandgap. The polymers adsorb onto the surface of nanostructured TiO2 due to interaction of the polar carboxylic acid units with the metal oxide surface. The resulting films absorb visible light strongly, and their spectra approximately mirror the polymers' solution absorption. Interestingly, a series of samples of 3a with different molecular weight (M-n) adsorb to TiO2 to an extent that varies inversely with M-n. DSSCs that utilize the donor acceptor polymers as sensitizers were tested using an I-/I-3(-) electrolyte. Importantly, for the set of polymer sensitizers 3a with varying M, the DSSC efficiency varies inversely with NI, a result that reflects the difference in adsorption efficiency observed in the film absorption experiments. The best DSSC cell tested is based on a sample of 3a with M-n similar to 4000, and it exhibits a similar to 65% peak IPCE with J(sc) similar to 12.6 mA cm-2 under AM 1.5 illumination and an overall power conversion efficiency of similar to 3%.