Synthesis and solid-state investigations of oligo-phenylene? : Ethynylene structures with halide end-groups

Jenny, Nicolas M. and Wang, Hong and Neuburger, Markus and Fuchs, Harald and Chi, Lifeng and Mayor, Marcel. (2012) Synthesis and solid-state investigations of oligo-phenylene? : Ethynylene structures with halide end-groups. European Journal of Organic Chemistry, 2012 (14). pp. 2738-2747.

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Official URL: http://edoc.unibas.ch/dok/A6031591

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In the field of material science functionalization of substrate surfaces (e.g. metal, graphite) with organic molecules is of increasing interest. Desirable targets are molecules with functional groups providing for two-dimensional assembly and three-dimensional crystal growth. We have synthesized a series of halogen-end-capped oligo-phenylene-ethynylenes (OPEs) to study the interactions at the solid/liquid interface and in crystal structures. Organohalides can be involved in a wide variety of intermolecular interactions such as C-X···H, C-X···X-C and C-X···pi-orbitals. The range of halogen-based interactions and the diversity of intermolecular forces along different crystal axes makes the investigation of such structures particular interesting and challenging. Here we probe the interplay of halide end-groups and the backbone of an OPE to investigate the intermolecular interactions in both solution depositions (2D) and X-ray crystal structures (3D). The STM images and the crystal structures of each OPE reveal striking packing similarities. For each molecule, a plane in the crystal structure with an arrangement of molecules resembling its two-dimensional packing on a flat surface was found. These results support the hypothesis of sheet-by-sheet crystal growth and suggest that flat surfaces would be ideal interfaces to promote crystal growth for halide-end-capped OPEs.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel and Neuburger, Markus and Jenny, Nicolas
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:05 Apr 2017 11:19
Deposited On:08 Nov 2012 16:17

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