Functionalized 4,4′-Bipyridines: Synthesis and 2D Organization on Highly Oriented Pyrolytic GraphiteClick to copy article linkArticle link copied!
- Jimmy RichardJimmy RichardInstitut de Chimie de Strasbourg, UMR 7177, CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67000 Strasbourg, FranceMore by Jimmy Richard
- Jean JosephJean JosephInstitut de Chimie de Strasbourg, UMR 7177, CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67000 Strasbourg, FranceMore by Jean Joseph
- Can WangCan WangUniversité de Strasbourg and CNRS, ISIS, 8 allée Gaspard Monge, 67000 Strasbourg, FranceMore by Can Wang
- Artur CiesielskiArtur CiesielskiUniversité de Strasbourg and CNRS, ISIS, 8 allée Gaspard Monge, 67000 Strasbourg, FranceMore by Artur Ciesielski
- Jean WeissJean WeissInstitut de Chimie de Strasbourg, UMR 7177, CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67000 Strasbourg, FranceMore by Jean Weiss
- Paolo Samorì*Paolo Samorì*Email: [email protected]Université de Strasbourg and CNRS, ISIS, 8 allée Gaspard Monge, 67000 Strasbourg, FranceMore by Paolo Samorì
- Victor Mamane*Victor Mamane*Email: [email protected]Institut de Chimie de Strasbourg, UMR 7177, CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67000 Strasbourg, FranceMore by Victor Mamane
- Jennifer A. Wytko*Jennifer A. Wytko*Email: [email protected]Institut de Chimie de Strasbourg, UMR 7177, CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67000 Strasbourg, FranceMore by Jennifer A. Wytko
Abstract

Commercial 4,4′-bipyridine is a popular scaffold that is primarily employed as a linker in 3D self-assembled architectures such as metallo-organic frameworks or as a connector in 2D networks. The introduction of alkyl substituents on the bipyridine skeleton is instrumental when 4,4′-bipyridines are used as linkers to form 2D self-assembled patterns on surfaces. Here, several synthetic strategies to access 4,4′-bipyridines functionalized at various positions are described. These easily scalable reactions have been used to introduce a range of alkyl substituents at positions 2 and 2′ or 3 and 3′ and at positions 2,2′ and 6,6′ in the case of tetra-functionalization. Scanning tunneling microscopy studies of molecular monolayers physisorbed at the graphite–solution interface revealed different supramolecular patterns whose motifs are primarily dictated by the nature and position of the alkyl chains.
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