Electrochemical Oxidation of 4-Ethenyl[22]paracyclophane: Cyclic Voltammetry, Electrosynthesis of Polymers, Analysis by Liquid Chromatography, and Mass Spectrometry

Autor:	Bernhard Robert Gollas, Ingrid Hesse, Ralf Lotz, Bernd Speiser, Harald Pasch, Ioannis Zagos
Rok vydání:	1997
Předmět:	Chromatography Electrospray ionization Organic Chemistry Size-exclusion chromatography General Chemistry Reversed-phase chromatography Electrosynthesis Mass spectrometry chemistry.chemical_compound Radical ion chemistry Physical and Theoretical Chemistry Cyclic voltammetry Acetonitrile
Zdroj:	Liebigs Annalen. 1997:2255-2264
ISSN:	1099-0690 0947-3440
DOI:	10.1002/jlac.199719971112
Popis:	4-Ethenyl[22]paracyclophane is oxidized electrochemically at a platinum electrode in acetonitrile/0.1 M tetra-n-butylammonium hexafluorophosphate. Its behavior in electro-oxidation is compared to that of styrene. Cyclic voltammetry proves diffusion controlled, direct one-electron oxidation of the hydrocarbon. The product of preparative scale electrolysis is analyzed by elemental analysis and various spectroscopic techniques. Bond formation occurs at the vinyl group, resulting in analogues of polystyrene. Polymers are separated on a reversed phase chromatography column, and online coupling to electrospray ionization mass spectrometry as well as a combination of size exclusion chromatography and MALDI-MS prove the formation of species up to the undecamer. The determination of the molecular product masses allows the assignment of the polymer end groups. A mechanistic hypothesis for the radical cation induced electropolymerization of the monomer is developed from the electro-chemical and structural results.
Databáze:	OpenAIRE
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