G. Brewer, C. Luckett / Inorganica Chimica Acta 358 (2005) 239–245
241
give a straw-colored solution. Salicylaldehyde (367 mg,
3.02 mmol) was added and the mixture immediately
turned yellow. It was stirred for an additional 20 min.
FeCl3 (328 mg, 2.02 mmol) in methanol was added
and the reaction mixture immediately turned purple.
The mixture was stirred for ꢀ5 min before sodium
hydroxide (490 mg, 12 mmol) was added. During the
following 15–20 min, the reaction mixture gradually
turned red. Concentration of the reaction mixture gave
0.887 g of a red powder. The red solid was dissolved
in CH2Cl2 (45 ml) and the solution was filtered to re-
move a whitish-tan solid (90 mg). The filtrate was evap-
orated to give a red powder.
the organic layer. The organic layer was removed and
concentrated to yield a purple solid (16 mg, termed
SP1). Elution of the column with more concentrated so-
dium chloride did not result in movement of the dark
band at the top of the column. This band was isolated
by transferring the top portion of the column into a
separatory funnel containing dichloromethane (30 ml).
Aqueous sodium hydroxide was added dropwise until
the purple color moved into the organic phase. This
was drawn off and concentrated to yield a few mg of
purple solid termed SP2.
3. Results and discussion
2.2.4. [Fetren(sal)x(4-CH3ImH)y](ClO4)y (x + y = 3)
4-Methyl-5-imidazolecarboxaldehyde (330 mg, 3.00
mmol) was added to a solution of tren (293 mg, 2.00
mmol) in methanol (25 ml). The mixture was stirred
and warmed for ꢀ20 min, during which time the solu-
tion became pale yellow. Salicylaldehyde (367 mg, 3.02
mmol) was added and the mixture immediately turned
a darker yellow. The reaction mixture was stirred and
warmed for 20 min more. Iron(III)chloride (331 mg,
2.04 mmol) in methanol (5 ml) was added and the reac-
tion mixture immediately turned purple. After 5 min of
stirring while maintaining heating, potassium acetate
(296 mg, 3.02 mmol) in methanol (5 ml) was added
and the mixture was stirred and warmed for 15 min. So-
dium perchlorate (847 mg, 6.0 mmol) in methanol (5–10
ml) was added and the reaction mixture was set aside to
concentrate. A purple powder (1.5 g) was isolated by
filtration.
3.1. Synthesis
The synthesis of asymmetric ligands from the Schiff
base condensation of symmetric polyamines with differ-
ent aldehydes is a challenge. Examples of structurally
verified successes that come about as a result of a spe-
cific condition (solubility, choice of carbonyl compound
or metal, or stoichiometry) include complexes contain-
ing 1,2-diaminobenzene [8], 1,3-diaminopropane [9]
and 1,2-diaminoethane [10]. The chemistry of asymmet-
ric copper imidazole complexes, and their use as build-
ing blocks for larger assemblies, has recently been
reviewed [11]. Specifically with tren there is a report of
a structurally characterized asymmetric complex with
lanthanum(III) in which only one of the tren arms forms
a Schiff base condensate with salicylaldehyde [12]. How-
ever, this method is not of general applicability to tran-
sition metal ions or in fact to other lanthanide ions and
must be regarded as a special case governed by the size
and solubility of the ion selected. With iron there are re-
ports of the syntheses of [Fetren(py)2(6-CH3py)]X2 and
2.2.5. [Fetren(sal)x(4-CH3Im)y] (x + y = 3)
Application of [Fetren(sal)x(4-CH3ImH)y](ClO4)y
(100 mg) as a solid to the top of a dry packed alumina
column followed by elution with methanol/dichloro-
methane (50/50) resulted in elution of a focused dark
blue band. Concentration afforded 46 mg of a dark pur-
ple solid.
[Fetren(py)(6-CH3py)2]X2 ðX ¼ ClO4 or PF6ꢁÞ that
ꢁ
rely on stoichiometric control. Specifically the authors
stated that these complexes could be prepared by simply
controlling the stoichiometric amount of aldehyde used
and the order of addition of the aldehydes [7]. The pre-
sumed resultant asymmetric complexes were character-
ized by bulk methods including elemental analysis, IR,
and Mo¨ssbauer data. It should be pointed out that these
methods would fail to conclusively distinguish a true
asymmetric complex such as [Fetren(py)2(6-CH3py)]X2
from a bulk mixture, [Fetren(py)x(6-CH3py)y]X2, in
which the ratio of py/6-CH3py was 2:1. Such distinction
could only be made on the basis of more specific meth-
ods such as mass spectroscopy or X-ray crystallography
that would give a singular result for each molecule in
question. Since a method existed in the literature for
the preparation of iron complexes of tren and mixed
py/6-CH3py complexes it was decided to follow this
methodology to determine if it worked in that case
and if so, to extend it to other mixed aldehyde cases.
2.2.6. Separation of [Fetren(sal)x(4-CH3ImH)y]-
(ClO4)y (x + y = 3)
A solution of [Fetren(sal)x(4-CH3ImH)y](ClO4)y (75
mg) in water to which a small amount of methanol
was added was applied to the top of a Sephadex SP
G25 ion exchange column (3 · 75) that had been al-
lowed to swell for several days prior to use in aqueous
sodium chloride. The dark purple solution bound tightly
to the top of the column and was not eluted by aqueous
NaCl solutions below 0.3 M. A dark purple band eluted
with 1.0 M aqueous sodium chloride leaving another
dark band at the top of the column. This fraction was
added to a separatory funnel which contained dichloro-
methane (20 ml). Aqueous sodium hydroxide (0.10 M)
was added dropwise until the purple color moved into