Synthesis and characterization of copper(I) complexes with triazole derivative ligands containing an α-diimine moiety

Article abstract of DOI:10.1080/15421400600788740

Two cuprous complexes Cu(L1)(PPh₃)I (1) and Cu(L2)(PPh₃)I (2) were obtained by reaction of Cu(PPh₃)₃I (PPh₃ = triphenylphosphine) with two different α-diimine ligands L₁(3, 5-di(2′-pyridyl)

Full text of DOI:10.1080/15421400600788740

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Synthesis and Characterization
of Copper(I) Complexes with
Triazole Derivative Ligands
Containing an α-Diimine Moiety
Wen-Jwu Wang a , Chien-Ho Lin a , Jau-Shuenn Wang
a & Shang-Wei Tang a
a Department of Chemistry , Tamkang University ,
Tamsui, Taipei, Taiwan (ROC)
Published online: 21 Dec 2006.
To cite this article: Wen-Jwu Wang , Chien-Ho Lin , Jau-Shuenn Wang & Shang-Wei
Tang (2006) Synthesis and Characterization of Copper(I) Complexes with Triazole
Derivative Ligands Containing an α-Diimine Moiety, Molecular Crystals and Liquid
Crystals, 456:1, 209-219, DOI: 10.1080/15421400600788740
To link to this article: http://dx.doi.org/10.1080/15421400600788740
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Mol. Cryst. Liq. Cryst., Vol. 456, pp. 209–219, 2006
Copyright # Taylor & Francis Group, LLC
ISSN: 1542-1406 print=1563-5287 online
DOI: 10.1080/15421400600788740
Synthesis and Characterization of Copper(I)
Complexes with Triazole Derivative Ligands
Containing an a-Diimine Moiety
Wen-Jwu Wang
Chien-Ho Lin
Jau-Shuenn Wang
Shang-Wei Tang
Department of Chemistry, Tamkang University, Tamsui,
Taipei, Taiwan (ROC)
Two cuprous complexes Cu(L1)(PPh3)I (1) and Cu(L2)(PPh3)I (2) were obtained by
reaction of Cu(PPh3)3I (PPh3 ¼ triphenylphosphine) with two different a-diimine
ligands L1(3,5-di(20-pyridyl)-4-amino-1,2,4-triazole) and L2 (N-benzylidene-3,5-
di (20-pyridyl)-4-amino-1,2,4-triazole, respectively. These two complexes have been
characterized by UV-Vis, luminescence, 1H NMR spectroscopy and cyclic voltam-
metric studies. The structures are confirmed by the single crystal X-ray diffraction
study. The compound Cu(L1)(PPh3)I (1) crystallizes in the triclinic space group
P-1 with a¼8.3188(14), b¼9.2243(15), c¼21.177(4), a¼78.156(3), b¼86.45(3),
c ¼ 65.966(3), Z ¼ 2 and the compound Cu(L2)(PPh3)I (2) crystallizes in the
triclinic space group P-1 with a ¼ 8.9671(7), b ¼ 13.9737(11), c ¼ 14.6850(12),
a ¼ 82.2580(10), b ¼ 75.7020(10), c ¼ 72.2790(10), Z ¼ 2. Both complexes show
an MLCT band at 340 ꢀ 545 nm region and complex 2 exhibits luminescence at
room temperature in a dichloromethane solution. The cyclic voltammogram of
Cu(L1)(PPh3)I shows the redox couples at þ 0.36 and ꢁ 0.545 V.
Keywords: a-diimine ligands; luminescence; triazole; X-ray
INTRODUCTION
It is known that mixed ligand Cu(I) complexes exhibit unusually
efficient [1–6], long-lived photoluminescence signals because of the
This work was supported by the National Science Council of Taiwan (ROC) and
Tamkang University.
Address correspondence to Wen-Jwu Wang, Department of Chemistry, Tamkang
University, Tamsui 25137, Taipei, Taiwan (ROC). E-mail: wjw@mail.tku.edu.tw
209

210
W.-J. Wang et al.
lowest energy (charge-transfer) state of d10 system, which involves
excitation from a metal to ligand (dpꢂ) orbital [7]. Moreover, their
rather flexible coordination geometry and strong bonding to pyridine-
donors have contributed to their widespread application. For example,
Cu(I) complexes, including those with aromatic a-diimine ligands,
have been widely studied with regard to luminescence [8–15].
Recently, Wang and co-workers have been demonstrated phosphor-
escent Cu(I) complexes to be promising phosphorescent emitters in
OLEDs [16]. This prompted us to undertake a programme in the devel-
opment of new phosphorescent Cu(I) compounds. The previously
reported Cu(I) complexes are mononuclear green emitters that contain
a phenanthroline N,N-chelate (or a derivative) and two phosphine
donors, which have been shown by McMillin and co-workers to play
a key role in stabilizing the Cu(I) center [5,17]. In our laboratory, we
have synthesized two new Cu(I) complexes based on 3,5-di(20-
pyridyl)-4-amino-1,2,4-triazole and a derivative ligand (Scheme 1).
Herein, we report the syntheses, structural characterization,
luminescent and electrochemical properties of Cu(L1)(PPh3)I and
Cu(L2)(PPh3)I.
SCHEME 1 Synthesis of Ligands and complexes.

Synthesis and Characterization of Copper(I) Complexes
211
EXPERIMENTAL
Synthesis of Ligands and Complexes
3,5-Di(2 0-pyridyl)-4-amino-1,2,4-triazole [18] (L1)
A mixture of 2-cyanopyridine (10.4 g, 0.1mol), hydrazine dihydro-
chloride (10.5 g, 0.1mol) and hydrazine hydrate (15g, 0.3mol) in
ethylene glycol (50 mL) were heated at 130ꢃC for 6hr. After cooling
the reaction mixture was diluted with water (200 mL). The precipitate
thus obtained was filtered, washed with water, dried and recrystal-
lized from ethanol as a white powder. The yield was 10.1g (85%).
1H-NMR (300MHz, CD3CN) d(ppm), J (Hz): 8.7 (d, 2H, bi-py-H,
J ¼ 4.6), 8.26 (d, 2H, bi-py-H, J ¼ 8.1), 8.13 (s, 1H, -NH), 7.96 (t, 2H,
bi-py-H, J ¼ 7.8), 7.46 (t, 2H, bi-py-H, J ¼ 6.2).
N-benzylidene-3,5-Di(20-pyridyl)-4-amino-1,2,4-triazole)
[19] (L2)
The ligand L1 (8g, 33.6 mmol), benzaldehyde (14.25g, 34.4mmol)
and two drops of concentrated H2SO4 were dissolved in absolute
ethanol (40 mL) and heated to reflux for 5hr under a N2 atmosphere.
After cooling the solution and on evaporation, the product was
obtained as an oil, which was precipitated by addition of 10 mL ether.
The resulting solid was filtered, washed with ether, dried and recrys-
tallized from ethanol as white powder. The yield was 8.8g (80%).1H-
=
NMR (300MHz, CD3CN) d(ppm), J (Hz): 8.75(s, 1H, ꢁHC N), 8.53
(d, 2H, bi-py-H, J ¼ 5.3), 8.12 (d, 2H, bi-py-H, J ¼ 8.3), 7.91 (t, 2H,
bi-py-H, J ¼ 8.7), 7.76 (d, 2H, Ar-H, J ¼ 7.3), 7.60 (t, 1H, Ar-H,
J ¼ 3.6), 7.52 (t, 1H, Ar-H, J ¼ 7.4), 7.40 (t, 2H, bi-py-H, J ¼ 6.2).
Anal. calcd for C19H14N6: C, 69.92; H, 4.32; N, 25.75. Found: C,
69.74; H, 4.36; N, 25.77.
Cu(L1)(PPh3)I (1)
Copper(I) iodide (95 mg, 0.5 mmol) dissolved in CH3CN (15 mL) was
added slowly to an acetonitrile solution (15 mL) of triphenylphosphine
(PPh3, 400 mg, 1.5mmol). The mixture was stirred for 10min at room
temperature. Then L1 (119mg, 0.5 mmol) dissolved in CH3CN (15mL)
was added slowly into the Cu(PPh3)3I solution. The color of the result-
ing solution appeared as light yellow. The solution was then stirred for
30 mins at room temperature to complete the reaction and the yellow
oil obtained on evaporation was precipitated by the addition of ether
(10 mL). The resulting was filtered, washed with ether, dried and
recrystallized from acetonitrile. The yellow crystals were separated.
1
The yield was 252 mg (73%). H-NMR (300 MHz, CD3CN) d (ppm),

212
W.-J. Wang et al.
J (Hz): 8.67 (d, 2H, bi-py-H, J ¼ 4.6), 8.39 (d, 2H, bi-py-H, J ¼ 4.6),
7.99 (t, 2H, bi-py-H, J ¼ 8.2), 7.48 (t, 2H, bi-py-H, J ¼ 6.5), 7.39 (m,
17H, Ar-H). Anal. calcd for C30H25CuIN6P: C, 52.15; H, 3.65; N,
12.16. Found: C, 52.32; H, 3.68; N, 11.95.
Cu(L2)(PPh3)I (2)
The compound Cu(L2)(PPh3)I was obtained by the same procedure
as describe above. Yield of the yellow crystal after recrystallization
1
from CH3CN in a 75% yield. H-NMR (300 MHz, CD3CN) d (ppm),
=
J (Hz): 8.72 (s, 1H, ꢁHC N), 8.54 (d, 2H, bi-py-H, J ¼ 5.3), 8.22
(d, 2H, bi-py-H, J ¼ 7.8), 7.96 (t, 2H, bi-py-H, J ¼ 8.0), 7.89 (d, 2H,
Ar-H, J ¼ 8.1), 7.67 (t, 1H, Ar-H, J ¼ 7.5), 7.56 (t, 2H, Ar-H,
J ¼ 7.5), 7.38 (m, 14H, Ar-H and 2H, bi-py-H). Anal. calcd for
C37H29CuIN6P: C, 57.04; H, 3.75; N, 10.79. Found: C, 57.19; H, 3.77;
N, 10.84.
RESULTS AND DISCUSSION
Ligand and Complexes
The ligands L1 and L2 are excellent bidentate chelators which bind to
Cu(I) ions. The reactions of these ligands with the stoichiometric
amount of Cu(PPh3)3I resulted in good yields of the corresponding yel-
low crystals of Cu(I) complexes, Cu(L1)(PPh3)I (1) and Cu(L2)(PPh3)I
(2), respectively. At the time of recrystallization, we obtained the
X-ray quality single crystals, which are stable in solution under
air. The structures of these complexes were therefore determined by
single-crystal X-ray diffraction analysis.
Molecular Structure
Crystal data are listed in Table 1 and selected bond parameters are
summarized in Table 2. The molecular structures of compounds 1
and 2 are shown in Figure 1. Compound 1 and 2 belong to the triclinic
space group P-1. The Cu(I) ion of these compounds have a distorted
tetrahedral geometry with one PPh3, one I- and one diimine ligand.
There is a significant difference between the two Cu-N bond lengths.
In both cases, it was observed that Cu-N(pyridyl) bond length is longer
than that of Cu-N(triazole) bond length: (Cu(1)-N(1) (pyridyl) 2.145(4)
˚
˚
A; Cu(1)-N(2) (triazole, 2.050(4) A for 1 and, Cu(1)-N(6) (pyridyl),
˚
˚
2.1369(19) A; Cu(1)-N(4) (triazole, 2.1028(19) A for 2). This indicates
that the triazole nitrogen atom is a stronger donor than that of the
pyridyl nitrogen.

Synthesis and Characterization of Copper(I) Complexes
213
TABLE 1 Crystal Data and Structure Refinement for Cu(L1)(PPh3)I and
Cu(L2)(PPh3)I
Parameter
Cu(L1)(PPh3)I
Cu(L2)(PPh3)I
Formula
Mw
C30 H25 Cu I N6 P
690.97
C37 H29 Cu I N6 P
779.07
T=K
298(2)
0.71073
Tricilinic
P-1
298(2)
0.71073
Tricilinic
P-1
˚
Wavelength, A
Crystal system
Space group
˚
a(A)
8.3188(14)
9.2243(15)
21.177(4)
78.156(3)
86.450(3)
65.966(3)
1452.1(4)
2
8.9671(7)
13.9737(11)
˚
b(A)
˚
˚
c(A)
14.685(12) A
a (deg)
b(deg)
c(deg)
82.2580(10)
75.702(10)
72.279(10)
3
3
˚
˚
V(A )
1694.9(2) A
2
Z
D
calc, gcmꢁ3
l, cmꢁ1
1.580
1.900
1.527
1.638
H, deg
F(000)
0.98 to 28.34
688
2.03 to 28.34
780
Limiting indices
ꢁ10 ꢄ h ꢄ 10,
ꢁ12 ꢄ k ꢄ 11,
ꢁ27 ꢄ l ꢄ 27
17435=6904=0.0351
95.2%
Full-matrix
least-squares on F2
6904=0=352
1.059
ꢁ11 ꢄ h ꢄ 11,
ꢁ18 ꢄ k ꢄ 18,
ꢁ19 ꢄ l ꢄ 19
2024=8029=0.0205
95.1%
Full-matrix
least-squares on F2
8029=0=415
1.043
Reflcns collcd=unique=Rint
Completeness to theta ¼ 28.28
Refinement method
Data=restr=params
GOF on F2
Final [I > 2 r(I)]
R1
wR2
0.0553
0.1258
0.0338
0.0768
R (all data)
R1
0.0844
0.0420
wR2
0.1440
0.807 and ꢁ0.600
0.0804
0.729 and ꢁ0.228
ꢁ3
˚
Largest diff. peak and hole (e. A
)
1H NMR Spectra
1
The H-NMR spectra of compounds 1 and 2 at 298 K are shown in
Figure 2. The spectra display only one set of chemical shifts, which
does not conform to the asymmetric structure of the compounds in
the solid state as established by their crystal structure. Wang and
co-worker have studied the variable temperature (298 to 203 K)
1H-NMR spectra of [HB(7-aza)3](Cu(PPh3)) (7-aza ¼ 7-azaindolyl)

214
W.-J. Wang et al.
ꢃ
˚
TABLE 2 Selected Bond Distances (A) and Angles ( )
Cu(L1)(PPh3)I
Cu(1)-N(1)
Cu(1)-N(2)
Cu(1)-P(1)
Cu(1)-I(1)
2.145(4)
2.050(4)
2.1981(12)
2.5746(7)
N(2)-Cu(1)-N(1)
N(2)-Cu(1)-P(1)
N(1)-Cu(1)-P(1)
N(1)-Cu(1)-I(1)
N(1)-Cu(1)-I(1)
P(1)-Cu(1)-I(I)
78.16(14)
112.43(11)
114.97(10)
113.60(11)
106.25(10)
122.70(14)
Cu(L2)(PPh3)I
Cu(1)-N(4)
Cu(1)-N(6)
Cu(1)-P(1)
Cu(1)-I(1)
2.1028(18)
2.1369(19)
2.1984(6)
2.6155(4)
N(4)-Cu(1)-N(6)
N(4)-Cu(1)-P(1)
N(6)-Cu(1)-P(1)
N(4)-Cu(1)-I(1)
N(1)-Cu(1)-I(1)
P(1)-Cu(1)-I(I)
77.55(7)
124.15(6)
115.22(6)
100.90(6)
103.82(5)
124.51(19)
complex [20]. As the temperature is lowered gradually, all peaks
become broad. At 233 K, each of the 7-azaindolyl peaks is resolved into
two peaks with 1:2 ratio. This is consistent with the presence of a
dynamic exchange process between the two coordinated 7-azaindolyl
groups, and the non-coordinated 7-azaindolyl group. Hence, this led
us to believe that the seemingly symmetric structure based on NMR
data at room temperature for compounds 1 and 2 is most likely a
consequence of dynamic exchange.
FIGURE 1 Crystal structure of Cu(L1)(PPh3)I and Cu(L2)(PPh3)I.

Synthesis and Characterization of Copper(I) Complexes
215
FIGURE 2 1H-NMR spectrum of 1 (up) and 2 (bottom) in CD3CN.
Spectroscopic and Electrochemical Properties
The absorption spectra of the free ligands L1, and L2 have two absorp-
tion bands at kmax value 255 (e ¼ 1.4ꢅ 104 Mꢁ1cmꢁ1) and 295 nm
(e ¼ 2.5 ꢅ 104 Mꢁ1cmꢁ1) attributed to the intraligand (p-pꢂ) transition.
In CH2Cl2, the absorption spectra of complex 2 has similar features as
the ligands (Fig. 3).
In addition to the high energy absorption bands, complex 2 shows a
weak and broad low-energy shoulder in the 340–545 nm region, which
accounts for the yellow color of the complex. The same trend was also
observed for the absorption spectra of complex 1, due to the low-energy
transition involving the low-lying unoccupied pꢂ orbital in N,N-chelate
ligand and the electron-rich Cu(I) ion. In addition, this low-energy
transition band resembles the MLCT band observed in [Cu(Phen)-
(PPh3)2]BF4 [5,17]. The MLCT bands of 1 and 2 shift towards a shorter
wavelength in the polar solvent CH3CN, as show in Figure 3, which
is consistent with the behavior of related Cu(I) phenanthroline
complexes.

216
W.-J. Wang et al.
FIGURE 3 UV=Vis spectrum of L2, 2 in 5ꢅ 10ꢁ5 M CH2Cl2 (left), and 2 in
5 ꢅ 10ꢁ5 M CH2Cl2, CH3CN (right).
When irradiated by UV light, the free ligands emit a weak blue color
with kmax 310–420 nm in CH2Cl2 solution at ambient temperature. This
band is assigned to fluorescence emission originating from a ligand-
centered p-pꢂ transition. In contrast to the behavior of the free ligands,
complex 2 displays a weak yellow emission with kmax ¼ 636 nm in
CH2Cl2 solution at ambient temperature (Fig. 4). The excitation spec-
tra for complex 2 confirms the presence of two absorption bands at
about 375 and 480 nm, which is confirmed by the absorption spectra
of 2 with an MLCT band at (340 ꢀ 545 nm). The phosphorescence of
FIGURE 4 Emission (dashed line) and excitation (solid line) spectrum of 2 in
5 ꢅ 10ꢁ5 M CH2Cl2.

Synthesis and Characterization of Copper(I) Complexes
217
[Cu(Phen)(PPh3)2]BF4 [5,17] was studied by McMillin and co-workers
and at a lower temperature (77K) they observed an emission decay
time of 0.22 ms. Hence, we suggest that the emission of complex 2
maybe due to phosphorescence.
The redox properties of ligands and complexes were examined by
cyclic voltammetry using a glassy carbon as working electrode in
CH3CN solution and in the presence of TBAPF6 as a supporting elec-
trolyte. The potentials are expressed with reference to the silver-silver
chloride electrode (RE). The cyclic voltammogram of ligand L1 shows
two redox couples, one is negative to RE ([L1]=[L1ꢁ] at Epc ¼ ꢁ 1.97 V)
and other is positive to RE ([L1]=[L1þ ], at Epa ¼ þ1.37 V). As the
triazole ring contains three N atoms and is more electron rich than
that of pyridine, which contains one N atom, the former corresponds
to the irreversible reduction of pyridine=pyridineꢁ, and the latter to
the irreversible oxidation of triazole=triazoleþ . On comparing the
redox behavior of the free ligand, complex 1 exhibits [1]=[1ꢁ],
[1ꢁ]=[12 ꢁ ], [1]=[1þ ] and [1þ ]=[12 þ ], at E ¼ ꢁ 0.545 V, Epc ¼ ꢁ1.60V,
E ¼þ0.36V, E ¼ þ 0.685 V, respectively, vs. RE in CH3CN solution
at ambient temperature (Fig. 5). In a study by Zacharias and
Masood, the redox behavior of the Cu(I) center in [Cu(phen)2]þ [21]
showed the stripping peak of Cu(I)=Cu(0) at Epc ¼ ꢁ 0.62V vs. SCE
in CH3CN. This behavior is due to the absence of bulky groups at
2,9-position of o-phenanthroline, so that the complex [Cu(phen)2]þ
FIGURE 5 Cyclic voltammogram of 1 in CH3CN solution (0.01M TBAPF6,
glassy carbon electrode, 100 mV=s scan rate, current range 100uA).

218
W.-J. Wang et al.
easily decomposes to Cu(0) and free ligand. At the same time, they
observed the redox couple of Cu(I)=Cu(II) at E¼þ0.6V. In our system,
we also observed a stripping peak at Epc¼ ꢁ0.13V in the reduction
region and a reversible couple at E¼þ0.685 V in the oxidation region.
Hence, the former corresponds to the reduction of Cu(I)=Cu(0), and the
latter is the reversible oxidation of Cu(I)=Cu(II). In contrast to the tri-
phenylphosphineanalogue complexes [22], the redox behavior of PPh3
at Epc¼ ꢁ1.60 V undergoes irreversible reducꢁtion. Finally, we determ-
ined the irreversible redox couple of Iꢁ=I3 at E¼þ0.36 V in the
oxidation region, in agreement with the redox behavior of Iꢁ from
CuI at E¼þ0.36 V.
CONCLUSIONS
We have synthesized the diimine ligands benzylidene-3,5-Di(20-
pyridyl)-4-amino-1,2,4-triazole (L1) and N-benzylidene-3,5-Di(20-
pyridyl)-4-amino-1,2,4-triazole (L2) which were used to prepare
complexes 1 and 2 with Cu(PPh3)3I. The two copper complexes were
structurally characterized by X-ray and 1H-NMR methods. The
absorption spectra of complexes 1 and 2 showed an MLCT bond in
the region of 345–545 nm. We have also measured the emission
properties of complex 2 which was shown to have a kmax ¼ 636 nm.
Cyclic valtammogram of complex 1 showed the redox couples of the
copper center at E ¼ ꢁ0.545V and E ¼ þ 0.685 V, the former corre-
sponds to the reduction of Cu(I)=Cu(0), and the latter corresponds to
the reversible oxidation of Cu(I)=Cu(II).
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