[2,2';5',2'']terthiophene-3-carboxylic acid | 380630-95-5

• 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: [2,2';5',2'']terthiophene-3-carboxylic acid
• 英文别名: 3′-(carboxylic acid)-2,2′:5′,2′′-terthiophene；Poly(5,2a(2):5a(2),2a(2)a(2)-terthiophene-3a(2)-carboxylic acid)；2,5-dithiophen-2-ylthiophene-3-carboxylic acid
• CAS: 380630-95-5
• 化学式: C₁₃H₈O₂S₃
• 分子量: 292.403
• InChiKey: VALZWDDRDFLHDY-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±45.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2,2';5',2'']terthiophene-3-carboxylic acid 、 1-羟基苯并三唑 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [2,2';5',2'']terthiophene-3-carboxylic acid benzotriazol-1-yl ester
  参考文献：
  名称：

  Organic surface modification using stable conducting materials

  摘要：

  通过使用稳定导电材料，如经OBT功能化的聚噻吩，实现了氨基酸和有机分子在导电表面上的高效固定化方法，这种方法便于在导电和半导电表面上引入特定结构基元。通过保护羧酸、接着进行Stille交叉偶联反应、酸脱保护及利用HOBT（羟基苯并三唑）和EDC酯化，完成了电聚合单体的合成。该单体对应的聚合物5（聚合物5–铂）在铂电极上表现出优异的稳定性，如循环伏安法所示，允许在功能化聚合物表面引入多种氨基酸和有机分子。经修饰的表面（聚合物6–铂）通过ATR红外光谱表征，显示出对应于氨基酸酰胺的羰基伸缩振动。

  DOI：

  10.1039/c2nj40366h
• 作为产物：
  描述：

  2,5-二溴噻吩-3-羧酸甲酯 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 52.5h， 生成 [2,2';5',2'']terthiophene-3-carboxylic acid
  参考文献：
  名称：

  Organic surface modification using stable conducting materials

  摘要：

  通过使用稳定导电材料，如经OBT功能化的聚噻吩，实现了氨基酸和有机分子在导电表面上的高效固定化方法，这种方法便于在导电和半导电表面上引入特定结构基元。通过保护羧酸、接着进行Stille交叉偶联反应、酸脱保护及利用HOBT（羟基苯并三唑）和EDC酯化，完成了电聚合单体的合成。该单体对应的聚合物5（聚合物5–铂）在铂电极上表现出优异的稳定性，如循环伏安法所示，允许在功能化聚合物表面引入多种氨基酸和有机分子。经修饰的表面（聚合物6–铂）通过ATR红外光谱表征，显示出对应于氨基酸酰胺的羰基伸缩振动。

  DOI：

  10.1039/c2nj40366h

文献信息

• Facile potentiostatic preparation of functionalized polyterthiophene-anchored graphene oxide as a metal-free electrocatalyst for the oxygen reduction reaction
  作者：M. Halappa Naveen、Hui-Bog Noh、Md Shahriar Al Hossain、Jung Ho Kim、Yoon-Bo Shim

  DOI：10.1039/c4ta06774f

  日期：——

  2′′-terthiophene (TBA) and 3′-(carboxylic acid)-2,2′:5′,2′′-terthiophene (TCA) were synthesized and polymerized with as-prepared GO to form complexes by a potential cycling method. The aminopyrimidyl groups on the poly(APT) backbone served as effective functional groups in the oxygen reduction reaction. The APT–GO complex was formed through hydrogen bonding and a ring-opening reaction of the epoxide group with

  开发新型催化剂以实现高性能，具有成本效益的氧气还原对于燃料电池的商业化至关重要。我们在这里展示了功能化的聚对噻吩锚定的氧化石墨烯（GO）复合材料作为新的非金属催化剂进行氧还原反应的用途。包含单体3'-（2-氨基嘧啶基）-2,2'：5'，2''-对噻吩（APT），3'-（p的不同官能团-苯甲酸）-2,2'：5'，2''-对噻吩（TBA）和3'-（羧酸）-2,2'：5'，2''-对噻吩（TCA）合成并聚合通过潜在的循环方法与制备的GO形成络合物。聚（APT）主链上的氨基嘧啶基在氧还原反应中充当有效的官能团。APT-GO络合物是通过氢键和环氧基团与胺的开环反应形成的一个新的C-N键而形成的。观察到，聚合物基体中的C–N键参与了O 2到H 2 O的直接电催化还原。聚（APT–GO）复合材料对燃料穿越和长期电极表现出更好的耐受性稳定性优于市售的Pt / C电极。
• Thiophene-Based Conjugated Polymers with Photolabile Solubilizing Side Chains
  作者：Zachary C. Smith、Dianne M. Meyer、Marc G. Simon、Cristian Staii、Deepak Shukla、Samuel W. Thomas

  DOI：10.1021/ma502289n

  日期：2015.2.24

  This paper describes a series of thiophene-based conjugated polymers that become insoluble upon irradiation with ultraviolet light. Stille or Suzuki reactions of appropriately substituted 2,5-bromothiophene derivatives yielded terthiophene and polythiophene derivatives with either o-nitrobenzyl (ONB) ester or ONB ether photolabile side chains with n-octyl substituents. Light-induced cleavage of these ONB side chains with ultraviolet light at 365 nm cleaves the octyl chains responsible for solubilization of the polymers away from the conjugated main chains, rendering them insoluble. Consistent with the accepted mechanism of ONB photolysis, those structural modifications that would yield a more stable benzylic radicalmethyl substitution on the benzylic position, replacement of the ester with an ether, or bothyielded more efficient photolyses as determined by (i) quantum yields of photolysis of ONB-substituted terthiophenes, and (ii) the percentage of polymer that persists in UV-irradiated thin films upon rinsing with chloroform. These polymers behave as negative-tone photoresists, enabling both direct photopatterning of conjugated polymers, and fabrication of multilayer conjugated polymer films by irradiating with UV light after each spin-casting step. Although hole-mobility values of these polymers in thin film transistors were only similar to 10(-5) cm(2) V-1 s(-1), photolysis and rinsing did not cause significant degradation in performance.
• NOVEL TERTHIOPHENE-3-CARBOXYLIC ACID COMPOUND AND FABRICATING METHOD THEREOF, FUNCTIONALIZED CONDUCTIVE TERTHIOPHENE POLYMER WITH THE COMPOUND AS A MONOMER, AND PROCESS FOR DNA HYBRIDIZATIOON DETECTION USING THE POLYMER
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：EP1425275B1

  公开（公告）日：2007-11-28
• US7161013B2
  申请人：——

  公开号：US7161013B2

  公开（公告）日：2007-01-09
• [EN] AN ELECTROCHEMICAL SENSOR AND RELATED METHODS<br/>[FR] CAPTEUR ÉLECTROCHIMIQUE ET PROCÉDÉS ASSOCIÉS
  申请人：ISIS INNOVATION

  公开号：WO2015075466A1

  公开（公告）日：2015-05-28

  Disclosed herein is a method of (and a sensor for) determining the presence of and/or concentration of superoxide anions in a sample of interest, the method comprising: • (a) providing an electrically conducting substrate having on a surface thereof a paste comprising an organic liquid binder and electrically conductive particles dispersed in the binder, contacting the paste with the sample of interest, wherein, if superoxide anions are present in the sample of interest, at least some of the superoxide anions are incorporated within the paste, wherein a first species is present within the paste at the time of contacting the paste with the sample of interest or a first species is incorporated into the paste after the contacting of the paste with the sample of interest, the superoxide anions then reacting with the first species to form a second species, • (b) using the electrically conducting substrate, having on a surface thereof the paste, produced in step (a) as a working electrode in an electrochemical test that involves altering the potential at a working electrode to a potential at which the first and/or second species is oxidised or reduced and obtaining electrochemical information, • (c) using the electrochemical information to determine the presence of and/or concentration of superoxide anions in the sample of interest.