Tuning Reactivity of Platinum(II) Complexes

C
H 3
I
H O
II
O
III
O
CH 3
N
10
O
N
+
I
NH 4 OAc N
Scheme 3.8: Synthesis of 4’–(2’’’–CH3–Ph)–2,2’:6’,2’’–terpyridine ligand
One equiv. of 2-acetylpyridine (II) was reacted with one equiv. of [2-
methylbenzaldehyde (I) in acetonitrile to yield the enone intermediate [2-CH3-1-{3-(2-
pyridyl)-3-oxo-prophenyl} benzene] (III) as yellow solid in high yield. To the suspension
of the enone and ammonium acetate in boiling ethanol was added the enolate
acylpyridinium iodide salt, N-{1-(2’-pyridyl)-oxo-2-ethyl}pyridinium iodide (IV) and
heated under reflux for 2 h. the product was collected by filtration, washed with 50%
ethanol and dried in vacuo. Colourless crystals of the required ligand, 4’–(2–CH3–
phenyl)–2,2’:6’,2’’–terpyridine (V) were obtained when crystallized from ethanol.
The ligand was characterised by elemental analysis, 1H NMR, 13C NMR, UV-Vis
spectrophotometry, and GC-MS. 4’–(2–CH3–phenyl)–2,2’:6’,2’’–terpyridine (V): Anal.
Calcd for C22H17N3: C, 81.7; H, 5.3; N, 13.0. Found: c, 81.6; H, 5.0; N, 13.0%.
3.2.1.8 Synthesis of [Pt{4'–(2"'–CH3-phenyl)–2,2’:6’,2’’–terpyridine}Cl]CF3SO3
(CH3PhPtCl)
Synthesis of the complex CH3PhPtCl followed literature procedure as described by
Summerton 18 (Scheme 3.9).
IV
N
V
CH 3
N