Organic Chemistry

Synthesis, Properties, and Intermolecular Interactions in the Solid States of π-Congested X-Shaped 1,2,4,5-Tetra(9-anthryl)benzenes

Authors

Abstract

A Negishi coupling based synthesis of 1,2,4,5-tetra(9-anthryl)benzene derivatives, possessing X-shaped molecular structures, is described. The results of X-ray crystallographic analysis show that two-dimensional highly ordered packing structure of the crystalline state of the unsubstituted derivative is a consequence of intermolecular π-π and CH-π interactions between anthracene units. Photoirradiation of the unsubstituted derivative as a precipitated solution promotes intramolecular [4+4] photocycloaddition reactions between both adjacent pairs of anthracene units to produce a crystalline polycyclic product having a unique 1.700 Å long carbon-carbon single bond. Furthermore, charge-transfer complexes, displaying near-infrared absorption and emission, are generated by co-crystallization of the X-shaped unsubstituted member of the group with electron-acceptor molecules.

Content

Thumbnail image of 1,2,4,5-tetra(9-anthryl)benzene.pdf

Supplementary material

Thumbnail image of SI_1,2,4,5-tetra(9-anthryl)benzene.pdf
Supporting information
Experimental Details, Synthesis of Materials, Supplementary Figures and Tables, and Charts of 1H and 13C NMR Spectra
Thumbnail image of Crystal structure of 4a.cif
Cif file of 4a
Crystal data of 4a
Thumbnail image of Crystal structure of 4a-PI.cif
Cif file of 4a-PI
Crystal data of 4a-PI
Thumbnail image of Crystal structure of 4b.cif
Cif file of 4b
Crystal data of 4b
Thumbnail image of Crystal structure of 4c.cif
Cif file of 4c
Crystal data of 4c
Thumbnail image of Crystal structure of 4b+F4TCNQ_CT.cif
Cif file of CT complex between 4b and F4-TCNQ
Crystal structure of CT complex between 4b and F4-TCNQ
Thumbnail image of Crystal structure of 4b+TCNB_CT.cif
Cif file of CT complex between 4b and TCNB
Crystal structure of CT complex between 4b and TCNB