2,2':5',2''-Terthiophene (α-Terthiophene)
(Synonyms: alpha-三联噻吩,α-?Terthiophene; α-Terthienyl; Trithiophene) 目录号 : GC30211
2,2':5',2''-Terthiophene (α-Terthiophene) (α-Terthiophene) 是杂环噻吩的低聚物。
Cas No.:1081-34-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2,2':5',2''-Terthiophene (α-Terthiophene) is an oligomer of the heterocycle thiophene. 2,2':5',2''-Terthiophene has been employed as building block for the organic semi-conductor polythiophene.
In the most common isomer of Terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.
[1]. Casado J, et al. Alternated quinoid/aromatic units in terthiophenes building blocks for electroactive narrow band gap polymers. Extended spectroscopic, solid state, electrochemical, and theoretical study. J Phys Chem B. 2005 Sep 8;109(35):16616-27.
| Cas No. | 1081-34-1 | SDF | |
| 别名 | alpha-三联噻吩,α-?Terthiophene; α-Terthienyl; Trithiophene | ||
| Canonical SMILES | C1(C2=CC=C(C3=CC=CS3)S2)=CC=CS1 | ||
| 分子式 | C12H8S3 | 分子量 | 248.39 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°C, protect from light, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.0259 mL | 20.1296 mL | 40.2593 mL |
| 5 mM | 0.8052 mL | 4.0259 mL | 8.0519 mL |
| 10 mM | 0.4026 mL | 2.013 mL | 4.0259 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A theoretical study on the low-lying excited states of 2,2':5',2''-Terthiophene and 2,2':5',2'':5'',2'''-quaterthiophene
Chemphyschem 2005 Jul 11;6(7):1357-68.15942967 10.1002/cphc.200400487
The nature and properties of the low-lying singlet and triplet valence excited states of 2,2':5',2''-Terthiophene (terthiophene) and 2,2':5',2'':5'',2'''-quaterthiophene (tetrathiophene) are discussed on the basis of high-level ab initio computations. The spectroscopic features determined experimentally for short alpha-oligothiophenes are rationalised on theoretical grounds. Special attention is devoted to the nonradiative decay process through intersystem crossing (ISC) from the singlet to the triplet manifold, which is known to be relatively less efficient in tetrathiophene. Along the geometry relaxation of the S1 state of terthiophene, the S1 and T2 states become degenerate, which leads to a favourable situation for the occurrence of ISC. The parallel process is expected to be less favoured in tetrathiophene because of the less efficient spin-orbit coupling and the increase of the S1-T2 energy gap.
Simultaneous electro-generation/polymerization of Cu nanocluster embedded conductive poly(2,2':5',2''-Terthiophene) films at micro and macro liquid/liquid interfaces
Sci Rep 2023 Jan 21;13(1):1201.36681717 PMC9867727
Cu nanoparticles (NPs) have been shown to be excellent electrocatalysts, particularly for CO2 reduction - a critical reaction for sequestering anthropogenic, atmospheric carbon. Herein, the micro interface between two immiscible electrolyte solutions (ITIES) is exploited for the simultaneous electropolymerization of 2,2':5',2''-Terthiophene (TT) and reduction of Cu2+ to Cu nanoparticles (NPs) generating a flexible electrocatalytic composite electrode material. TT acts as an electron donor in 1,2-dichloroethane (DCE) through heterogeneous electron transfer across the water|DCE (w|DCE) interface to CuSO4 dissolved in water. The nanocomposite formation process was probed using cyclic voltammetry as well as electrochemical impedance spectroscopy (EIS). CV and EIS data show that the film forms quickly; however, the interfacial reaction is not spontaneous and does not proceed without an applied potential. At high [TT] the heterogeneous electron transfer wave was recorded voltammetrically but not at low [TT]. However, probing the edge of the polarizable potential window was found to be sufficient to initiate electrogeneration/electropolymerization. SEM and TEM were used to image and analyze the final Cu NP/poly-TT composites and it was discovered that there is a concomitant decrease in NP size with increasing [TT]. Preliminary electrocatalysis results at a nanocomposite modified large glassy carbon electrode saw a > 2 × increase in CO2 reduction currents versus an unmodified electrode. These data suggest that this strategy is a promising means of generating electrocatalytic materials for carbon capture. However, films electrosynthesized at a micro and ~ 1 mm ITIES demonstrated poor reusability.
Photo-induced transformations in 2,2':5',2''-Terthiophene thin films on silver
Phys Chem Chem Phys 2006 Mar 28;8(12):1445-50.16633627 10.1039/b515379d
We report on transient photo-induced structural changes of 2,2':5',2''-Terthiophene (3T) adsorbed on silver nanoparticles. Surface-enhanced Raman scattering (SERS) data show that the film thickness predetermines the eventual course of these changes. In particular, for high molecular concentrations (thick adsorbate layers), illumination leads to a photoinduced polymerization of the 3T film. For thin layers ( approximately monolayer coverage), the photoinduced spectral evolution is qualitatively different. We interpret the latter process as a cleavage of the terthiophene molecule, resulting in isolated thiophene units. Calculations of excitation energies for 3T + 3Ag+ and 1T + Ag+ revealed visible transitions, while calculated Raman frequencies indicated 1T as a possible photoproduct. As no photoinduced transformations are observed for 3T in the solid or solution phases, it is likely that the processes reported here originate in surface-enhanced charge-transfer between the Ag-surface and the organic adsorbate.
Silver-Catalysed Hydroarylation of Highly Substituted Styrenes
Angew Chem Int Ed Engl 2021 Apr 6;60(15):8537-8541.33493358 10.1002/anie.202016268
Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes, however most of these reports examine the hydroarylation of unpolar, β-mono- or β-unsubstituted styrenes, while exploring mainly electron-rich benzene nucleophiles. Herein, we report a mild and general catalytic system for the selective hydroheteroarylation of multiply substituted styrenes and heteroaromatic styrenes. Mechanistic analysis of the reaction led to the discovery of commercially available 2,2':5',2''-Terthiophene as a key reagent.
Wavelength-Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine-Bis(Carboxamide)-Terthiophene Sensitizer
Chemistry 2020 Jun 5;26(32):7274-7280.32157735 10.1002/chem.202000587
Lanthanide ion (LnIII ) complexes, [Ln(3Tcbx)2 ]3+ (LnIII =YbIII , NdIII , ErIII ) are isolated with a new pyridine-bis(carboxamide)-based ligand with a 2,2':5',2''-Terthiophene pendant (3TCbx), and their resulting photophysical properties are explored. Upon excitation of the complexes at 490 nm, only LnIII emission is observed with efficiencies of 0.29 % at 976 nm for LnIII =YbIII and 0.16 % at 1053 nm for LnIII =NdIII . ErIII emission is observed but weak. Upon excitation at 400 nm, concurrent 1 O2 formation is seen, with efficiencies of 11 % for the YbIII and NdIII complexes and 13 % for the ErIII complex. Owing to the concurrent generation of 1 O2 , as expected, the efficiency of metal-centered emission decreases to 0.02 % for YbIII and 0.05 % for NdIII . The ability to control 1 O2 generation through the excitation wavelength indicates that the incorporation of 2,2':5',2''-Terthiophene results in access to multiple sensitization pathways. These energy pathways are unraveled through transient absorption spectroscopy.