4-(4-(Didecylamino)styryl)-N-methylpyridinium iodide
[CAS# 95378-73-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 4-(4-(Didecylamino)styryl)-N-methylpyridinium iodide
• Synonyms: N,N-didecyl-4-[(E)-2-(1-methylpyridin-1-ium-4-yl)ethenyl]aniline iodide
• Molecular Formula: C₃₄H₅₅IN₂
• Molecular Weight: 618.72
• CAS Registry Number: 95378-73-7
• SMILES: CCCCCCCCCCN(CCCCCCCCCC)C1=CC=C(C=C1)/C=C/C2=CC=[N+](C=C2)C.[I-]

Discovory and Applicatios

4-(4-(Didecylamino)phenylvinyl)-N-methylpyridinium iodide, commonly known as DASPMI, is a fluorescent dye molecule that is widely known for its unique chemical structure and applications in fluorescence microscopy, bioimaging, and analytical chemistry. The development of DASPMI stems from the search for a new type of fluorescent dye that can emit strong fluorescence upon binding to a specific biological target or environment. Researchers focused on enhancing the photophysical properties of phenylvinyl dyes by introducing long alkyl chains (didecylamino groups) and optimizing the molecular structure to achieve high quantum yield and photostability. This effort led to the synthesis of DASPMI, which is designed to meet the stringent requirements of modern fluorescence imaging techniques and biochemical assays. The N-methylpyridine core is the central chromophore responsible for fluorescence emission upon excitation. The phenylvinyl group contains an extended conjugated system that enhances light absorption and fluorescence emission. The didecylamino substituent provides solubility in nonpolar solvents and promotes membrane permeability, making it suitable for cell imaging applications.

DASPMI is widely used as a fluorescent probe for visualizing cellular structures, organelles, and biomolecules within living cells. Its ability to selectively stain cell membranes and subcellular compartments is invaluable in studying cellular dynamics and physiological processes. The dye's high photostability and bright fluorescence emission enable its application in super-resolution microscopy techniques such as STED (stimulated emission depletion) and PALM (photoactivated localization microscopy), allowing researchers to achieve nanoscale imaging resolution.

DASPMI is used in ion channel studies to monitor changes in membrane potential and ion flux across cell membranes. Its sensitivity to changes in membrane potential makes it suitable for studying neuronal activity and cardiac electrophysiology. DASPMI is used as a fluorescent sensor to detect biomolecules, environmental pollutants, and analytes in biological samples. The specific interactions and fluorescence response of DASPMI facilitate sensitive and rapid detection methods in analytical chemistry.

DASPMI is incorporated into optoelectronic devices such as organic light-emitting diodes (OLEDs) and photovoltaic cells due to its efficient light emission and charge transport properties, helping to improve the performance and efficiency of devices in light emission and energy conversion applications. DASPMI is used to develop photonic materials and sensors for light modulation, optical data storage, and telecommunication technologies, taking advantage of its tunable optical properties and compatibility with a variety of substrates.