65287-01-6

Usage

Usage

Biological stain and redox indicator
Widely used as a biological stain and a redox indicator

Chemical Structure

Benzothiazole ring fused to a dimethylamine-linked phenyl group
Formed by a benzothiazole ring fused to a dimethylamine-linked phenyl group

Substituent

Sulphonatopropyl
A sulphonatopropyl substituent that provides water solubility

Properties

Antimicrobial and antiparasitic
Possesses antimicrobial and antiparasitic properties

Medical Application

Treatment of methemoglobinemia
Used in the treatment of methemoglobinemia

Potential Applications

Photodynamic therapy and anti-cancer agent
Has potential applications in photodynamic therapy and as an anti-cancer agent

Mechanism of Action

Generation of reactive oxygen species upon light activation
Ability to generate reactive oxygen species upon light activation

Additional Properties

Neuroprotective and anti-inflammatory
Possesses neuroprotective and anti-inflammatory properties

Promising Candidate

Treatment of neurodegenerative diseases
Making it a promising candidate for the treatment of neurodegenerative diseases

InChI:InChI=1/C12H15NO3S2/c1-9-4-5-12-11(8-9)13(10(2)17-12)6-3-7-18(14,15)16/h4-5,8H,3,6-7H2,1-2H3

Upstream product

• 1120-71-4 1,3-propanesultone 
• 95-26-1 2,5-dimethylbenzothiazole 

Relevant academic research and scientific papers

Accumulation of the photonic energy of the deep-red part of the terrestrial sun irradiation by rare-earth metal-free: E - Z photoisomerization

Large scale solar energy storage in the form of E-Z photoisomerisable organic materials requires avoidance of applying rare earth metals at any stage of the process used. Here, drastic shortening of the synthetic route of crown ether functionalized hemicyanine dyes, suitable for efficient E-Z photoisomerization under extremely low excitation light intensities compared with unconcentrated sunlight is reported. The higher energetic form was successfully stabilized by rare earth free cations-in this case by styryl dye-Ba2+ complexes. For the first time E-Z photoisomerization was demonstrated and was observed directly by excitation with light substantially red-shifted compared to the absorption spectrum of the trans-to-cis active moieties via the process of triplet-triplet annihilation upconversion.

Precious metal-free molecular machines for solar thermal energy storage

Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans-cis photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV-vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability constants of metal complexes were determined and are in good agreement with the literature data for reference dyes. The temporal evolution of trans-to-cis isomerization was observed in a real-time regime. The dyes demonstrated a low intrinsic fluorescence of their Ba2+ complexes and high yield of E/Z photoisomerization with lifetimes of the higher energy form longer than 500 seconds. Density functional theory (DFT) calculations at the B3LYP/6-31+G(d,p) level were performed in order to predict the enthalpies (H) of the cis and trans isomers and the storage energies (ΔH) for the systems studied.