Binary charge-transfer complexes using pyromellitic acid dianhydride featuring C-H⋯O hydrogen bonds.

Tania N Hill,Andreas Lemmerer

doi:10.1107/s2056989018015645

Abstract

Four binary charge-transfer complexes were made using pyromellitic acid dianhydride (pmda), those being pmda-naphthalene (1/1), C10H2O6·C10H8, (I), pmda-fluoranthene (1/1), C10H2O6·C16H10, (II), pmda-9-methyl-anthracene (1/1), C10H2O6·C15H12, (III), and pmda-ethyl anthracene-9-carboxyl-ate (1/2), C10H2O6·2C17H12O3, (IV). All charge-transfer complexes show alternating donor and acceptor stacks, which have weak C-H⋯O hydrogen bonds connecting the donor and acceptor mol-ecules. In addition, complex (I) has Z' = 1/2, complex (II) has a Z' = 2 and complex (IV) has half mol-ecule of pyromellitic acid dianhydride in the asymmetric unit.

Highlights

Crystal engineering, the conception and synthesis of molecular solid state structures, is fundamentally based upon the discernment and subsequent exploitation of intermolecular interactions
Non-covalent bonding interactions are primarily used to achieve the organization of molecules and ions in the solid state in order to produce materials with desired properties. and this understanding using a variety of intermolecular interactions is at the very heart of crystal engineering
An important interaction is that of charge transfer (CT) between an electron-rich -system and an electron-poor system (Herbstein, 2005)

Summary

Chemical context

The conception and synthesis of molecular solid state structures, is fundamentally based upon the discernment and subsequent exploitation of intermolecular interactions. An important interaction is that of charge transfer (CT) between an electron-rich -system (donor) and an electron-poor system (acceptor) (Herbstein, 2005). Aromatic hydrocarbons with strongly polarizing groups, such as 1,3,5-trinitrobenzene (TNB), have an electron-poor -system and are classified as the acceptor molecule (Hill et al, 2018a,b). Another common acceptor molecule is pyromellitic acid dianhydride (pmda), which has electron-withdrawing O atoms of the carboxylic acid dianhydride groups. E74, 1772–1777 research communications (pyrene) (Kato et al, 2017) To this end, we have synthesized four new charge-transfer co-crystals that show no disorder: (pmda)Á(naphthalene) (I), (pmda)Á(fluoranthene) (II), (pmda)Á(9-methylanthracene) (III), and (pmda)2Á(9-ethyl ester anthracene) (IV). The intermolecular interactions of the DÁ Á ÁA stacks can be quantified using Hirshfeld surface analysis as well as the resulting fingerprint plots using the programme

Structural commentary

Supramolecular features