title: Synthesis and characterization of a helicene-based imidazolium salt and its application in organic molecular electronics.
abstract: Herein we demonstrate the synthesis of a helicene-based imidazolium salt. The salt was prepared by starting from racemic 2-methyl[6]helicene, which undergoes radical bromination to yield 2-(bromomethyl)[6]helicene. Subsequent treatment with 1-butylimidazole leads to the corresponding salt 1-butyl-3-(2-methyl[6]helicenyl)-imidazolium bromide. The prepared salt was subsequently characterized by using NMR spectroscopy and X-ray analysis, various optical spectrometric techniques, and computational chemistry tools. Finally, the imidazolium salt was immobilized onto a SiO2 substrate as a crystalline or amorphous deposit. The deposited layers were used for the development of organic molecular semiconductor devices and the construction of a fully reversible humidity sensor.
authors.affiliation: Institute of Chemical Process Fundamentals of the AS CR, v.v.i. Praha 6,165 02 (Czech Republic). storchj@icpf.cas.cz.
authors.forename: Jan
authors.initials: J
authors.lastname: Storch
authors.forename: Jaroslav
authors.initials: J
authors.lastname: Zadny
authors.forename: Tomas
authors.initials: T
authors.lastname: Strasak
authors.forename: Martin
authors.initials: M
authors.lastname: Kubala
authors.forename: Jan
authors.initials: J
authors.lastname: Sykora
authors.forename: Michal
authors.initials: M
authors.lastname: Dusek
authors.forename: Vladimir
authors.initials: V
authors.lastname: Cirkva
authors.forename: Pavel
authors.initials: P
authors.lastname: Matejka
authors.forename: Milos
authors.initials: M
authors.lastname: Krbal
authors.forename: Jan
authors.initials: J
authors.lastname: Vacek
mesh_terms: D018360:Crystallography, X-Ray; D004581:Electronics; D007093:Imidazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011789:Quantum Theory; D012492:Salts / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D014867:Water / Q000032:analysis
chemical_list: D007093:Imidazoles; D011083:Polycyclic Compounds; D012492:Salts; C031660:helicenes; D014867:Water; D012822:Silicon Dioxide
keywords: helicenes; imidazolium salt; organic electronics; organic semiconductor; sensors