Isoindigo
(Synonyms: 异靛蓝) 目录号 : GC48860
A building block
Cas No.:476-34-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isoindigo is an electron-accepting building block.1,2 It has been used in the synthesis of polymers for use in organic photovoltaics.
1.Lei, T., Wang, J.-W., and Pei, J.Design, synthesis, and structure-property relationships of isoindigo-based conjugated polymersAcc. Chem. Res.47(4)1117-1126(2014) 2.Stalder, R., Mei, J., Graham, K.R., et al.Isoindigo, a versatile electron-deficient unit for high-performance organic electronicsChem. Mater.26(1)664-678(2013)
| Cas No. | 476-34-6 | SDF | |
| 别名 | 异靛蓝 | ||
| Canonical SMILES | O=C1NC2=C(C1=C3C(NC4=C3C=CC=C4)=O)C=CC=C2 | ||
| 分子式 | C16H10N2O2 | 分子量 | 262.3 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 10 mg/ml | 储存条件 | -20°C |
| 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 | 3.8124 mL | 19.0621 mL | 38.1243 mL |
| 5 mM | 0.7625 mL | 3.8124 mL | 7.6249 mL |
| 10 mM | 0.3812 mL | 1.9062 mL | 3.8124 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。
Recent Advances in Isoindigo-Inspired Organic Semiconductors
Chem Rec 2019 Jun;19(6):973-988.PMID:30375156DOI:10.1002/tcr.201800135.
Over the past decade, Isoindigo has become a widely used electron-deficient subunit in donor-acceptor organic semiconductors, and these isoindigo-based materials have been widely used in both organic photovoltaic (OPV) devices and organic field effect transistors (OFETs). Shortly after the development of isoindigo-based semiconductors, researchers began to modify the Isoindigo structure in order to change the optoelectronic properties of the resulting materials. This led to the development of many new isoindigo-inspired compounds; since 2012, the Kelly Research Group has synthesized a number of these Isoindigo analogues and produced a variety of new donor-acceptor semiconductors. In this Personal Account, recent progress in the field is reviewed. We describe how the field has evolved from relatively simple donor-acceptor small molecules to structurally complex, highly planarized polymer systems. The relevance of these materials in OPV and OFET applications is highlighted, with particular emphasis on structure-property relationships.
Isoindigo-Thiophene D-A-D-Type Conjugated Polymers: Electrosynthesis and Electrochromic Performances
Int J Mol Sci 2023 Jan 22;24(3):2219.PMID:36768544DOI:10.3390/ijms24032219.
Four novel isoindigo-thiophene D-A-D-type precursors are synthesized by Stille coupling and electrosynthesized to yield corresponding hybrid polymers with favorable electrochemical and electrochromic performances. Intrinsic structure-property relationships of precursors and corresponding polymers, including surface morphology, band gaps, electrochemical properties, and electrochromic behaviors, are systematically investigated. The resultant isoindigo-thiophene D-A-D-type polymer combines the merits of Isoindigo and polythiophene, including the excellent stability of isoindigo-based polymers and the extraordinary electrochromic stability of polythiophene. The low onset oxidation potential of precursors ranges from 1.10 to 1.15 V vs. Ag/AgCl, contributing to the electrodeposition of high-quality polymer films. Further kinetic studies illustrate that isoindigo-thiophene D-A-D-type polymers possess favorable electrochromic performances, including high optical contrast (53%, 1000 nm), fast switching time (0.8 s), and high coloration efficiency (124 cm2 C-1). These features of isoindigo-thiophene D-A-D-type conjugated polymers could provide a possibility for rational design and application as electrochromic materials.
Synthesis and Characterization of Isoindigo-Based Push-Pull Chromophores
J Org Chem 2020 Apr 3;85(7):4611-4618.PMID:32126766DOI:10.1021/acs.joc.9b03267.
Symmetrical and unsymmetrical chromophores of Isoindigo 3-7 were designed and synthesized, in which Isoindigo was used as the central unit (electron acceptor unit A), triphenylamine as the end capping unit (electron donor group D), 1,1,4,4-tetracyanobutadiene (TCBD, A') and cyclohexa-2,5-diene-1,4-diylidene-expanded TCBD (A″) as the acceptor unit. The effects of multiacceptor units on photophysical, electrochemical, and computational studies were investigated. The photophysical properties of Isoindigo 6 and 7 exhibit a strong intramolecular charge transfer (ICT) absorption band in the near IR region. The Isoindigo 4-7 shows multi-redox waves with a low electrochemical band gap, which signifies the tuning of highest occupied molecular orbital-lowest unoccupied molecular orbital energy levels and enhance the π-conjugation. The computational studies demonstrate that there is a good agreement with experimental data. The molecular design and synthesis of Isoindigo 4-7 gives a new avenue for the development of building blocks in organic electronics.
Recent advances in the application of Isoindigo derivatives in materials chemistry
Beilstein J Org Chem 2021 Jul 6;17:1533-1564.PMID:34290836DOI:10.3762/bjoc.17.111.
In this review, the data on the application of Isoindigo derivatives in the chemistry of functional materials are analyzed and summarized. These bisheterocycles can be used in the creation of organic solar cells, sensors, lithium ion batteries as well as in OFET and OLED technologies. The potentials of the use of polymer structures based on Isoindigo as photoactive component in the photoelectrochemical reduction of water, as matrix for MALDI spectrometry and in photothermal cancer therapy are also shown. Data published over the past 5 years, including works published at the beginning of 2021, are given.
Nanoscale isoindigo-carriers: self-assembly and tunable properties
Beilstein J Nanotechnol 2017 Feb 1;8:313-324.PMID:28243570DOI:10.3762/bjnano.8.34.
Over the last decade Isoindigo derivatives have attracted much attention due to their high potential in pharmacy and in the chemistry of materials. In addition, Isoindigo derivatives can be modified to form supramolecular structures with tunable morphologies for the use in drug delivery. Amphiphilic long-chain dialkylated isoindigos have the ability to form stable solid nanoparticles via a simple nanoprecipitation technique. Their self-assembly was investigated using tensiometry, dynamic light scattering, spectrophotometry, and fluorometry. The critical association concentrations and aggregate sizes were measured. The hydrophilic-lipophilic balance of alkylated Isoindigo derivatives strongly influences aggregate morphology. In the case of short-chain dialkylated Isoindigo derivatives, supramolecular polymers of 200 to 700 nm were formed. For long-chain dialkylated Isoindigo derivatives, micellar aggregates of 100 to 200 nm were observed. Using micellar surfactant water-soluble forms of monosubstituted 1-hexadecylisoindigo as well as 1,1'-dimethylisoindigo were prepared for the first time. The formation of mixed micellar structures of different types in micellar anionic surfactant solutions (sodium dodecyl sulfate) was determined. These findings are of practical importance and are of potential interest for the design of drug delivery systems and new nanomaterials.