1332849-23-6

Basic information

• Product Name: 2,3,3-trimethyl-1-(3-sulfonatepropyl)-3H-indolium
• CAS NO: 1332849-23-6
• Molecular Weight: 385.484
• Mol File: 1332849-23-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,3,3-trimethyl-1-(3-sulfonatepropyl)-3H-indolium(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,3-trimethyl-1-(3-sulfonatepropyl)-3H-indolium(1332849-23-6)
• EPA Substance Registry System: 2,3,3-trimethyl-1-(3-sulfonatepropyl)-3H-indolium(1332849-23-6)

Safety Data

• Hazardous Substances Data: 1332849-23-6(Hazardous Substances Data)

Usage

General Description

2,3,3-trimethyl-1-(3-sulfonatepropyl)-3H-indolium, also known as thiazole orange, is a fluorescent dye commonly used in molecular biology and biochemistry for staining nucleic acids. It is a cationic dye that binds to DNA and RNA, emitting strong green fluorescence upon binding. Thiazole orange is often used as a marker for nucleic acid quantification and visualization in techniques such as agarose gel electrophoresis and fluorescence microscopy. Its high affinity for nucleic acids and strong fluorescent properties make it a valuable tool for studying DNA and RNA in various research and diagnostic applications. Thiazole orange is also known for its potential as a DNA-intercalating agent and its use in the development of novel fluorescent probes for nucleic acid detection.

Upstream product

• 1640-39-7 2,3,3-trimethylindoleniune 
• 90-02-8 salicylaldehyde 
• 29636-96-2 N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium 

Downstream Products

• 90-02-8 salicylaldehyde 
• 29636-96-2 N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium 

Relevant articles and documents

Stability of merocyanine-type photoacids in aqueous solutions

Over the past years, protonated merocyanines (MEHs) have been used as photoacids to control various chemical, material, and biological processes using visible light. For the applications under aqueous conditions, stability of this type of photoacid has been a concern. While hydrolysis of merocyanines is well known, this work showed that deprotonation of MEH to form merocyanine is not necessary for the hydrolysis of MEH. The decomposition products were identified by ultraviolet-visible spectroscopy and liquid chromatography–mass spectrometry. Comparing the behaviors of different MEHs under different conditions indicates that the hydrolysis is catalyzed by OH? and thus MEHs are more stable at a lower pH. Modifying an MEH with an electron-donating group conjugated to the double bond significantly improved its stability. Photostability of an MEH was tested by conducting 100 irradiating/recovering cycles, and the photoacid showed good photostability.

Enhanced Photophosphorylation of a Chloroplast-Entrapping Long-Lived Photoacid

Enhancing solar energy conversion efficiency is very important for developing renewable energy, protecting the environment, and producing agricultural products. Efficient enhancement of photophosphorylation is demonstrated by coupling artificial photoacid

Light-Responsive Dynamic DNA-Origami-Based Plasmonic Assemblies

DNA nanotechnology offers a versatile toolbox for precise spatial and temporal manipulation of matter on the nanoscale. However, rendering DNA-based systems responsive to light has remained challenging. Herein, we describe the remote manipulation of native (non-photoresponsive) chiral plasmonic molecules (CPMs) using light. Our strategy is based on the use of a photoresponsive medium comprising a merocyanine-based photoacid. Upon exposure to visible light, the medium decreases its pH, inducing the formation of DNA triplex links, leading to a spatial reconfiguration of the CPMs. The process can be reversed simply by turning the light off and it can be repeated for multiple cycles. The degree of the overall chirality change in an ensemble of CPMs depends on the CPM fraction undergoing reconfiguration, which, remarkably, depends on and can be tuned by the intensity of incident light. Such a dynamic, remotely controlled system could aid in further advancing DNA-based devices and nanomaterials.

Long-lived photoacid based upon a photochromic reaction

A visible-light activatable photoacid has been studied, which upon irradiation, changes from a weak acid, with a pKa of 7.8, to a strong acid, which achieves nearly complete proton dissociation. This process is reversible and the half-life of t

Effects of Substituents on Metastable-State Photoacids: Design, Synthesis, and Evaluation of their Photochemical Properties

Recently, metastable-state photoacids have been widely used to control proton transfer in numerous chemical and biological processes as well as applications with visible light. Generally, substituents have a great influence on the photochemical properties of molecules, which will further affect their applications. Yet, the effects of substituents on metastable-state photoacids have not been studied systematically. In this work, 16 metastable-state photoacid derivatives were designed and synthesized on the basis of substituents having a large range of σ–π electron–donor–acceptor capabilities. The effects of substituents on the color display [or maximum absorption band(s)], solubility, pKa values, dark/photoacidity, photosensitivity, and relaxation kinetic(s) were investigated in detail. This study will be helpful for the targeted design and synthesis of promising photoacids and the application of their photocontrolled proton-release processes in functional materials/devices.