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Supramolecular Architecture of Substituted Tetraphenyl‐carbo‐benzenes from the Energetic Viewpoint
Author(s) -
Shishkina Svitlana V.,
Dyakonenko Viktoriya V.,
Shishkin Oleg V.,
Maraval Valérie,
Chauvin Remi
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201700584
Subject(s) - supramolecular chemistry , stacking , intermolecular force , chemistry , molecule , crystallography , homogeneous , aromaticity , stereochemistry , computational chemistry , crystal structure , thermodynamics , organic chemistry , physics
The use of DFT‐calculated energy‐vector diagrams (EVDs) featuring the topology of pairwise intermolecular interaction energies is applied to crystals of carbo‐benzenes. A homogeneous set of six ideally centrosymmetric tetraphenyl‐carbo‐benzenes is selected, with various substituents R in para positions: R =4‐anisyl, 1‐ethyl‐2‐phenyl‐1 H ‐indol‐3‐yl, 2‐chloro‐2‐(1‐ethyl‐2‐phenyl‐1 H ‐indol‐3‐yl)ethenyl, tetradecyl, and 9,9‐dihexyl‐9 H ‐fluoren‐2‐yl, 2‐(9,9‐dihexyl‐9 H ‐fluoren‐2‐yl)ethynyl. The basic structural motifs (BSMs) of the crystals vary from layers to columns, depending on the size and shape of the substituents R. The BSM cohesion is shown to rely on π‐stacking, CH‐π and dispersive interactions. Solvate molecules are shown to have a negligible role in the formation of the BSM, whereas they loosen the interaction between neighbouring BSMs.