Synthesis and Coordination Properties of 6,6'-Dimesityl-2,2'-bipyridine

Abstract

Suzuki C oupling, C op per(I) C om p lex, X -R ay D ataA synthetic route to 6,6'-d im esityl-2,2'-bipyrid in e is presented that involves a Suzuki c o u pling o f 6,6'-d ib rom o-2,2'-b ip yridin e with m esityl boronic acid. The new sterically crow ded ligand is in vestigated by X -ray analysis and its coordination behavior in the p resence o f co p p er(I) is exam in ed .

Synthesis, Coordination, and Spectroscopic Properties of 2,2′-Bipyridyldimesitylpalladium(II) and 6-Mesityl-2,2′-bipyridyldimesitylpalladium(II)

“…A strong support for the proposed ªcomplex based mechanismº comes from a recent report on the reaction of 2,2'-bipyridine with LiMes by Schmittel et. al., where under similar conditions a 60% yield for the 6-Mes-bpy product is found [3]. Under more vigorous conditions 3,3',6-trimesityl-bipyridine is formed in rather low yields.…”

“…A closer look ( Figure 2) reveals a nearly co-planar, graphite-like stacked arrangement of the two mesityl groups with rather short C±C contacts of 3.27 A Ê (C31±C11) or 3.32 A Ê (C35±C13), that is shorter than 3.354 A Ê found in graphite [5]. However, the tilt angle of the mesityl substituent on the bipyridine ligand of 65°is almost identical to those found for the free ligand 6,6'-Mes 2 -bpy (64.5°and 63°respectively) [3].…”

“…The synthesis and spectroscopic characterization of [(bpy)Pd(FMes) 2 ] (FMes = nonafluoromesityl or 2,4,6-tris-trifluoromethyl-phenyl) was recently reported by Espinet et al [2]. The molecular structure from X-Ray diffraction experiments reveals the effective axial shielding of the palladium atom from each one of the ortho-CF 3 (1) is the first step and under the choosen conditions only this molecule is accessible to arylation of the coordinated bipyridine ligand in the preferred 6-position. The product is the 6-mesitylated bipyridine complex 2.…”

Ferrocene Rotary Switches Featuring 2‐Pyridyl‐1,2,3‐triazole “Click” Chelates

“…Building on that work a second‐generation rotor was developed from the known Fc ligand, 1,1′‐di(5‐yl‐ethynyl‐2,20‐bipyridine)ferrocene (diebpyFc) [22] . Exploiting the HETPHEN strategy developed by Schmittel [23] addition of 6,6’‐dimesityl‐2,2’‐bipyridine (dimesbpy), [24] and [Cu(CH 3 CN) 4 ](PF 6 ) (2 equiv.) resulted in the formation of the dinuclear Cu(I) complex [(diebpyFc)Cu 2 (dimesbpy) 2 ](PF 6 ) 2 [21c] .…”

Synthesis and Light-Induced Actuation of Photo-Labile 2-Pyridyl-1,2,3-Triazole Ru(bis-bipyridyl) Appended Ferrocene Rotors

“…Previously our lab reported [ 61 , 62 ] the electrochemically driven expansion and contraction of Fc based molecular actuators/‘folding rulers’. The switching mechanism used in both of these systems exploits the switching system developed by Sauvage and Schmittel and co-workers [ 31 , 63 , 64 , 65 , 66 ]. Both ferrocene rotors bear 2,2′-bipyridine chelators able to bind Cu(I) ions in heteroleptic tetrahedral complexes with bulky 6,6′-dimesityl-2,2′-bipyridine ligands.…”