Abstract
The study aims to present a detailed theoretical investigation of noncovalent intermolecular interactions between different π–π stacking nitrogen substituted phenothiazine derivatives by applying second-order Møller-Plesset perturbation (MP2), density functional (DFT) and semiempirical theories. The conformational stability of these molecular systems is mainly given by the dispersion-type electron correlation effects. The density functional tight-binding (DFTB) method applied for dimer structures are compared with the results obtained by the higher level theoretical methods. Additionally, the optimal configuration of the investigated supramolecular systems and their self-assembling properties are discussed.
Highlights
Weak noncovalent intermolecular forces such as hydrogen bonds, π–π stacking play an important role in the formation of stable and structurally well-defined supramolecular structures [1,2]
The study of the gas-phase stacking interactions between the five natural DNA and RNA nucleobases and the four aromatic amino acid residues reveals that the largest stacking interactions between the natural nucleobases and amino acids approach the strength of the weakest hydrogen-bonding in DNA [7]
All these findings suggest that stacking interactions between the natural nucleobases and aromatic amino acids likely play a much bigger role in biological processes than previously anticipated
Summary
Weak noncovalent intermolecular forces such as hydrogen bonds, π–π stacking play an important role in the formation of stable and structurally well-defined supramolecular structures [1,2]. If we want to keep the high ordered structure given by the functional group, one need to have the top-parallel configuration for the linker unit This means that, one has to find out the optimal length of the alkyl chain which is long enough to facilitate the parallel aggregation of the phenothiazine aromatic rings but is reasonably short to not allow the appearance of the distorted oligomers. Heteroatoms in an aromatic system induce differentiation of (and) electron distributions; they influence stacking-type preferences This is due to the fact that, in the π–π parallel stacked aromatic arrangements, displacement of the rings favors the minimization of repulsive electrostatic component and the maximization of attractive contribution. Our calculations allow us to characterize the individual interactions between the nitro-substituted aromatic molecules, and thereby reveal the detailed contribution of different types of interactions giving a comprehensive picture of their stacking abilities
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