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Quantum Design and Synthesis of a Gasoline Marker Based on a Phenol‐Functionalized Supramolecular Quaternary‐Salt Complex
Ist Teil von
ChemistrySelect (Weinheim), 2023-09, Vol.8 (36)
Erscheinungsjahr
2023
Quelle
Wiley Online Library All Journals
Beschreibungen/Notizen
Abstract
We present the development of supramolecular surfactants (
SS
s) based on
MR
⋅⋅⋅
OA
⋅⋅⋅(
PhOH
)
i
complexes among methylene red (
MR
), oleyl amine (
OA
) and stoichiometric amounts
of phenol (
PhOH
), aimed at obtaining markers for the identification of gasolines by harnessing their supramolecular interactions‐mediated stability and homogeneous distribution within gasoline, as well as their very‐characteristic nuclear magnetic resonance (NMR), Fourier‐transform infrared (FTIR), and UV‐visible (UV‐vis) signals. Density functional theory (DFT), together with the conductor‐like screening model (COSMO), reveal that the supramolecular interactions are due to a non‐ionic to ionic reaction under which the carboxylic proton is transferred from
MR
to
OA
, and that
PhOH
confers solubility to
SS
s withing gasoline by hiding their ionic heads. The proton transference was confirmed by
1
H NMR and
13
C NMR, FTIR, and thermogravimetric analysis spectroscopies, whereas the solubility in gasoline through UV‐vis absorbance measurements that, together with viscosity measurements, also revealed that the maximum content of
PhOH
for adequate performance is
3, in agreement with DFT‐COSMO calculations, which predict that for
3 the
SS
s’ interaction energy per additional
PhOH
becomes weaker. All theoretical and experimental results support the viability of
MR
⋅⋅⋅
OA
⋅⋅⋅(
PhOH
)
i
complexes as gasoline markers due to their full compatibility with gasoline and their well‐defined spectroscopic‐fingerprints.