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Synthesis and Solid‐State Investigations of Oligo‐Phenylene–Ethynylene Structures with Halide End‐Groups

Nicolas M. Jenny

Department of Chemistry, University of Basel, St. Johanns‐Ring 19, 4056 Basel, Switzerland, Fax: +41‐61‐267‐1016

These authors contributed equally to this work.

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Hong Wang

Physical Institute, University of Münster, Wilhelm‐Klemm‐Strasse 10, 48149 Münster, Germany

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

These authors contributed equally to this work.

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Markus Neuburger

Department of Chemistry, University of Basel, St. Johanns‐Ring 19, 4056 Basel, Switzerland, Fax: +41‐61‐267‐1016

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Harald Fuchs

Physical Institute, University of Münster, Wilhelm‐Klemm‐Strasse 10, 48149 Münster, Germany

Karlsruhe Institute of Technology (KIT), Institute of Nanotechnology, P. O. Box 3640, 76021 Karlsruhe, Germany

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Lifeng Chi

Physical Institute, University of Münster, Wilhelm‐Klemm‐Strasse 10, 48149 Münster, Germany

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Marcel Mayor

E-mail address: [email protected]

Department of Chemistry, University of Basel, St. Johanns‐Ring 19, 4056 Basel, Switzerland, Fax: +41‐61‐267‐1016

Karlsruhe Institute of Technology (KIT), Institute of Nanotechnology, P. O. Box 3640, 76021 Karlsruhe, Germany

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First published: 04 April 2012

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Citations: 6

Abstract

We have synthesized a series of halogen‐end‐capped oligo‐phenylene‐ethynylenes to study interactions at the solid/liquid interface and in crystal structures. Here we probe the interplay and diversity of intermolecular interactions between halide end‐groups and oligo‐phenylene‐ethynylene backbones through solution depositions (2D) and X‐ray crystal structures (3D). The STM images and crystal structures reveal a striking complementarity in each case.

Abstract

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···π‐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.

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