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Comparative studies of the noncovalent interactions in the single‐crystal packing of pyrene, pyrene‐4,5‐dione, and pyrene‐4,5,9,10‐tetraone
Author(s) -
Zreid Monther,
Tabasi Zahra A.,
Zhao Yuming
Publication year - 2021
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4192
Subject(s) - pyrene , chemistry , supramolecular chemistry , non covalent interactions , density functional theory , crystal (programming language) , crystal engineering , molecular orbital , computational chemistry , crystallography , crystal structure , molecule , organic chemistry , hydrogen bond , computer science , programming language
Pyrene‐4,5‐dione and pyrene‐4,5,9,10‐tetraone are K‐region oxidized derivatives of pyrene, which show interesting structural and electronic properties as well as useful application in organic electronic and optoelectronic devices. The single‐crystal structures of pyrene and pyrene‐4,5‐dione have been published, but the crystallographic data of pyrene‐4,5,9,10‐tetraone has not. In this work, the single‐crystal structure of pyrene‐4,5,9,10‐tetraone has been clearly elucidated for the first time, and the detailed crystallographic properties were analyzed and discussed in comparison with those of pyrene and pyrene‐4,5‐dione. Various noncovalent interactions taking place within the supramolecular assemblies that exist in the crystal packing of these compounds were studied by Hirshfeld surface analysis and density functional theory (DFT) calculations. Our joint experimental and computational analyses provide fundamental understanding of the electron density properties, interaction energies, and frontier molecular orbital (FMO) properties for these pyrene systems and establish correlations of these properties with diverse supramolecular assembling motifs.