Synthesis and Characterization of a Helicene-Based Imidazolium Salt and Its Application in Organic Molecular Electronics

0440909 - ÚCHP 2016 RIV DE eng J - Journal Article
Storch, Jan - Žádný, Jaroslav - Strašák, Tomáš - Kubala, M. - Sýkora, Jan - Dušek, Michal - Církva, Vladimír - Matějka, P. - Krbal, M. - Vacek, J.
Synthesis and Characterization of a Helicene-Based Imidazolium Salt and Its Application in Organic Molecular Electronics.
Chemistry - A European Journal. Roč. 21, č. 6 (2015), s. 2343-2347. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA MPO FR-TI3/628; GA TA ČR TA04010082
Institutional support: RVO:67985858 ; RVO:68378271
Keywords : helicene * imidazolium salt * organic electronics
Subject RIV: CC - Organic Chemistry
Impact factor: 5.771, year: 2015

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.
Permanent Link: http://hdl.handle.net/11104/0244408