Supramolecular Control of Photochemical and Electrochemical Properties of Two Oligothiophene Derivatives at the Air/Water Interface

Abstract

Two geometric isomers of oligothiophene derivatives containing two crowned styryl fragments in 2- or 3-positions of thiophene rings are able to form stable monolayers on the water subphase. The organizing of crown-containing oligothiophenes in monolayers is guided by the π-stacking interaction of hydrophobic styrylthiophene fragments and interaction of hydrophilic macrocycles with the water subphase. The difference in structure of oligothiophene molecules leads to the formation of distinct monolayer architectures with various electrochemical and optical characteristics.

Supramolecular Assembly of Planar Systems from Modular Molecules with a Given Hydrophilic–Lipophilic Balance: Film Sensors with an Anthraquinone Signal Group

“…Here, low values of the monolayer area are registered. They correspond to this very orientation of aromatic moieties of the molecules [17][18][19][20][21].…”

Synthesis of Novel Fullerene-Porphyrin Conjugates for the Formation of Langmuir Monolayers

“…The in situ absorption and fluorescence spectra for the monolayers on the water surface under compression were recorded with the AvaSpec-2048 fiber optic spectrometer (Netherlands). [27][28] The subphase was deionized water. Chloroform of analytical grade (Merck) was used for solution preparation and as a spreading solvent.…”

Design and evaluation of sensory systems based on amphiphilic anthraquinones molecular receptors

“…However, as shown in our previous studies[32,33,37], changes of surface pressure-area isotherms upon addition of the metal ions cannot be regarded as an unambiguous proof of the binding process. To confirm the complexation of Hg 2+ , the monolayers should be further characterized by in situ fiber-optic reflectionabsorption spectroscopy.A reliable interpretation of spectroscopic data is possible only after estimation of aggregation of free ligands in the monolayer on the spectroscopic features of the monolayers.Indeed, the aggregation of ligand molecules in the monolayer and the complexation processes can induce similar spectroscopic changes insofar as the absorption spectra can show a shift of the ICT band maximum in both cases.…”

“…they take an «edge-on» orientation as a consequence of the stabilizing π-π stacking interactions. Evidently, low monolayer area values are recorded in such situations, which correspond precisely to such an orientation of the aromatic molecules [31][32][33][34][35]. In contrast, "face-on" orientation of anthraquinone moiety is preserved even at a high surface density of monolayer.…”