In this work, monomeric 3-([7]helicen-9-yl)thiophene was synthesized and used for the preparation of a polymeric film by electrosynthesis.

The synthesis of 2-bromo[6]helicene was revised and improved up to 51% yield. Its reactivity was thoroughly investigated, and a library of 17 different carbon, boron, nitrogen, phosphorus, oxygen and sulfur substituted derivatives was prepared. The racemization barrier for 2-bromo[6]helicene was determined, and the usage of enantiomers in the synthesis of optically pure helicenes was rationalized. The three most energy-demanding reactions using enantiomerically pure 2-bromo[6]helicene were tested in order to confirm the predicted enantiomeric excess.

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.

Achieving chiral plasmon response based on the combination of achiral plasmonic nanostructures with highly chiral surrounding medium represents an attractive way for creation of hybrid optically active plasmonic materials. In this work, we present an attractive design and fabrication of chiral plasmon substrates based on a surface plasmon-polariton-supported structure coupled with extremely optically active helicene enantiomers. Such approach allows us to excite chiral plasmon waves and to design optically active surfaceenhanced Raman spectroscopy substrates. Its further combination with standard Raman spectroscopy makes possible enantioselective detection/ recognition of optical enantiomers with detection limits below those of standard spectral techniques. The chiral optical response of new plasmonic system was observed and controlled by the optical rotation of helicenes. Without necessity of previous chiral separation or implementation of sophisticated experimental equipment, we were able to estimate the concentration of enantiomers in their mixture by using left-or right-handed chiral plasmon substrates.