(ФЕРРОЦЕНИЛМЕТИЛ) ДОДЕЦИЛДИМЕТИЛАММОНИЯ БРОМИД

Description

(Ferrocenylmethyl)dodecyldimethylammonium bromide is a cationic surfactant with a redox-active ferrocene head group: the metallocene fragment is linked through a methylene bridge to a dimethylammonium center bearing a long dodecyl (C12) alkyl chain, the counterion is bromide. The structure combines the classical architecture of a cationic surfactant (long hydrophobic tail plus charged head) with a reversibly oxidizable ferrocene moiety.

Synonyms

Dodecyl(ferrocenylmethyl)dimethylammonium bromide; (ferrocenylmethyl)dodecyldimethylammonium bromide.

Basic Attributes

• CAS No: 98778-40-6
• Chemical formula: C25H42BrFeN
• Molecular weight: 492.36
• Exact weight: 491.184998
• PSA: 0.00000
• XLogP3: 3.41200

Physico-chemical characteristics

• Melting point: 137 °C

Class of substance and principle of action

Belongs to the group of redox-switchable (“redox-active”) surfactants based on ferrocene. Oxidation of the ferrocene fragment to the ferrocenium cation increases the total positive charge of the head group and changes the hydrophilic-lipophilic balance of the molecule, which reversibly rearranges micelles, emulsions and surfactant films by electrochemical or chemical action without changing the reagent.

Scope of application

Used in laboratory studies of electrochemically controlled emulsions, foams and micellar solutions, where a change in the oxidation state of iron switches the state of aggregation of the dispersion. It is of interest for the development of systems for targeted delivery and release of substances controlled by a redox stimulus, as well as in fundamental work on the supramolecular and colloidal chemistry of metallocene surfactants.

Safety Information

Data on transport codes, hazard codes and GHS labeling for this compound are not available in the supplier dump and are not given in order to avoid introducing false values. Like most quaternary ammonium salts, the substance should be considered a potential skin and mucous membrane irritant until officially classified.

Storage

Store in a dry place, protected from light and moisture, in a tightly closed container, away from strong oxidizing agents - the metallocene fragment is sensitive to prolonged exposure to air and light.

Place in surfactant chemistry

Classic cationic surfactants (alkyltrimethylammonium salts, benzalkonium chloride) have a constant charge of the head group and switch the properties of the solution only by changing the concentration or temperature. The introduction of a ferrocene redox center into the head group adds another degree of control freedom—electrochemical potential, which makes such surfactants a tool for “smart” dispersed systems that respond to an external electrical signal without changing the composition of the solution.

Related compounds in the line

The compound belongs to the same family of methyleneferrocenyl derivatives as (ferrocenylmethyl)trimethylammonium iodide - the difference in the length and nature of the alkyl tail (dodecyl C12 chain instead of methyl groups), which transfers the substance from the class of electrochemical mediators to the class of surface-active redox-switchable systems.