Organotrifluoroborates as attractive self-assembling systems: the case of bifunctional dipotassium phenylene-1,4-bis(trifluoroborate).

Aurelia Falcicchio,Filippo M Perna,Corrado Cuocci,Donato I Coppi,Sten O Nilsson Lill,Antonio Salomone,Dietmar Stalke,Vito Capriati

doi:10.1039/c5dt02020d

Abstract

Highlights

The first structure of an aromatic bis(trifluoroborate) dipotassium salt, elucidated by the combination of crystallography, DFT calculations, topological and non-covalent interaction analysis, discloses a 3D network undergoing spontaneous self-assembly thanks to the massive participation of weak intra- and intermolecular interactions for which fluorine atoms proved to play a leading role
The design and synthesis of novel polyfunctional aromatic compounds carrying more than one trifluoroborate group onto the aromatic core is fascinating and challenging both from a crystallographic and a synthetic perspective in order to chemoselectively replace them in multistep organic synthesis and to obtain new functional structural motifs
A more detailed characterization of these interactions is found in Fig. S1 in the Electronic supplementary information (ESI).† The short distances between K⋯C were, by the bond critical point (BCP) and bond path analysis, found to be due to agostic interactions[20] between potassium and the aromatic CH hydrogens rather than due to the carbons

Summary

Introduction

The first structure of an aromatic bis(trifluoroborate) dipotassium salt, elucidated by the combination of crystallography, DFT calculations, topological and non-covalent interaction analysis, discloses a 3D network undergoing spontaneous self-assembly thanks to the massive participation of weak intra- and intermolecular interactions for which fluorine atoms proved to play a leading role. We present the first structural investigations on such a salt (2) which provide detailed insight on the presence of an impressive multitude of weak inter- and intramolecular interactions responsible for its self-assembly into a new 3D network.

Results

Conclusion