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

05 September 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

pi-cluster
anthracene
CH-pi interaction
photoisomerization
charge-transfer complex

Supplementary materials

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Description
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Supporting information
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Experimental Details, Synthesis of Materials, Supplementary Figures and Tables, and Charts of 1H and 13C NMR Spectra
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Cif file of 4a
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Crystal data of 4a
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Cif file of 4a-PI
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Crystal data of 4a-PI
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Cif file of 4b
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Crystal data of 4b
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Cif file of 4c
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Crystal data of 4c
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Cif file of CT complex between 4b and F4-TCNQ
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Crystal structure of CT complex between 4b and F4-TCNQ
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Cif file of CT complex between 4b and TCNB
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Crystal structure of CT complex between 4b and TCNB
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