J. Org. Chem. [CLAC/LASYROC/ISIS]

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.

Graphical Abstract :

Reference :

Jimmy Richard, Jean Joseph, Can Wang, Artur Ciesielski, Jean Weiss, Paolo Samorì, Victor Mamane, Jennifer A. Wytko

Functionalized 4,4′-Bipyridines: Synthesis and 2D Organization on Highly Oriented Pyrolytic Graphite

J. Org. Chem. 2021 – DOI : https://pubs.acs.org/doi/10.1021/acs.joc.0c02708

 

Contacts :

Jennifer A. Wytko and J. Weiss, équipe CLAC, Institut de Chimie (UMR 7177).

Victor Mamane, équipe LASYROC, Institut de Chimie (UMR 7177).