Some new nickel 1,2-dichalcogenolene complexes as single-component semiconductors

Article abstract of DOI:10.1515/znb-2007-0509

The complexes Ni(dmeds)(dmit), Ni(dmedt)(dmit), Ni(dpedt)(dsit), Ni(dpedt)(dmit), and Ni(dcdt)(dmit) (where dmeds is dimethylethylenediselenolate, dmedt is dimethylethylenedithiolate, dpedt is diphenylethylenedithiolate, dcdt is 1,2-bis-decylsulfanyl-ethe

Full text of DOI:10.1515/znb-2007-0509

Some New Nickel 1,2-Dichalcogenolene Complexes as Single-component
Semiconductors
George C. Papavassilioua, George C. Anyfantisa, Barry R. Steeleb, Aris Terzisc,
Catherine P. Raptopoulouc, George Tatakisd, George Chaidogiannosd, Nikos Glezosd,
Yufeng Wenge, Harukazu Yoshinoe, and Keizo Muratae
a Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation, 48,
Vassileos Constantinou Ave., Athens 116-35, Greece
b Organic Chemistry Institute, National Hellenic Research Foundation, Athens 116-35, Greece
c Institute of Materials Science, NCSR, Demokritos, Athens 153-10, Greece
d Institute of Microelectronics, NCSR, Demokritos, Athens 153-10, Greece
e Graduate School of Science, Osaka City University, Osaka 558-8585, Japan
Reprint requests to Prof. G. C. Papavassiliou. Fax (30210) 7273794. E-mail: pseria@eie.gr
Z. Naturforsch. 2007, 62b, 679 – 684; received November 29, 2006
The complexes Ni(dmeds)(dmit), Ni(dmedt)(dmit), Ni(dpedt)(dsit), Ni(dpedt)(dmit), and
Ni(dcdt)(dmit) (where dmeds is dimethylethylenediselenolate, dmedt is dimethylethylenedithio-
late, dpedt is diphenylethylenedithiolate, dcdt is 1,2-bis-decylsulfanyl-ethene-1,2-dithiolate, dmit is
1,3-dithiol-2-thione-4,5-dithiolate, and dsit is 1,3-dithiol-2-thione-4,5-diselenolate) were prepared
and characterized. The new complexes exhibit semiconducting behavior, with band gap values
around 0.8 eV.
Key words: Metal 1,2-Dichalcogenolenes, Single-component Semiconductors
Introduction
by liquid column chromatography. For one of them,
Ni(dmeds)(dmit), the crystal structure determination
is reported. All the complexes exhibit semiconduct-
ing behavior similar to that observed in Ni(pddt)(dmio)
and Ni(pddt)(dmit), where pddt is 6,7-dihydro-5H-1,4-
dithiepin-2,3-dithiolate and dmio is 1,3-dithiol-2-one-
4,5-dithiolate [3].
During the last five years a number of single-
component (neutral) metal 1,2-dichalcogenoleneshave
been prepared and studied in our laboratories and/or in
a collaboration with others [1 – 6]. Some unsymmetri-
cal complexes were found to be stable in air and solu-
ble in organic solvents. They exhibit strong nonlinear
optical (NLO) properties [5, 6] and/or show semicon-
ducting behavior under the conditions of field-effect
transistors (FETs) [3, 4].
Results and Discussion
From equimolar amounts of starting materi-
In this paper, the preparation and characterization als the unsymmetrical complexes Ni(dmeds)(dmit),
of Ni(dmeds)(dmit), Ni(dmedt)(dmit), Ni(dpedt)(dsit), Ni(dmedt)(dmit), Ni(dpedt)(dsit), Ni(dpedt)(dmit) and
Ni(dpedt)(dmit) and Ni(dcdt)(dmit) are described Ni(dcdt)(dmit) were obtained in 0.9, 2.4, 2.5, 21.0,
(where dmeds is dimethylethylenediselenolate [7, 8], and 0.8 % yields, respectively. The unsymmetrical
dmedt is dimethylethylenedithiolate [7], dpedt is complexes containing the ligands dmit, dsit (or
diphenylethylenedithiolate [7], dcdt is 1,2-bis-decyl- dmio) are expected to have redox-potential values
sulfanyl-ethene-1,2-dithiolate [9], dmit is 1,3-dithiol- higher than those of the corresponding symmetri-
2-thione-4,5-dithiolate [9, 10] and dsit is 1,3-dithiol-2- cal ones, Ni(dmedt)2, Ni(dmeds)2, Ni(dpedt)2 and
thione-4,5-diselenolate [9, 10]). These new unsymmet- Ni(dcdt)2, i. e., they are expected to be stable in air
rical (mixed ligand) complexes were prepared by the (see [3, 4, 7, 9, 10, 18, 19]). The new complexes were
cross-coupling method [2] according to the procedures found to be soluble in CS2 and some other organic sol-
of Scheme 1. The starting materials 1 – 5 were prepared vents. From the solutions single crystals and/or thin de-
by methods reported in [11 – 17] (see also [7, 8, 10]). posits of complexes on quartz and Si-SiO2 substrates
The required unsymmetrical complexes were sepa- were obtained. Solutions and thin deposits were found
rated from the corresponding symmetrical byproducts spectroscopically to be stable in air, as it was expected
0932–0776 / 07 / 0500–0679 $ 06.00 © 2007 Verlag der Zeitschrift fu¨r Naturforschung, Tu¨bingen · http://znaturforsch.com
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G. C. Papavassiliou et al. · Nickel 1,2-Dichalcogenolene Complexes as Single-component Semiconductors
Scheme 1. i = 1: NaOMe in MeOH,
i = 2: NiCl2 in MeOH, i = 3: aq. HCl
(35 %) in air.
from the electrochemical data, and moreover stable in dimers [20] with the inversion center sitting on the cen-
light for a long time. By treatment with NaBH4 in ace- ter of the Ni2Se2 core. The closest Ni···S and Ni···Se
tone and in the presence of Bu4N+ the anionic species bond lengths in the coordination sphere are ca. 2.2
˚
can be obtained.
and 2.3 A, respectively, while the longer Ni···Se
˚
bond (2.56 A) is responsible for the formation of the
Single crystals of Ni(dmeds)(dmit) had a rect-
angular shape and were found to be suitable for
X-ray crystal structure determination. The complex
Ni(dmeds)(dmit) crystallizes in the triclinic space
dimers. The closest intramolecular Ni···Ni distance is
˚
ca. 3.06 A. It was found that the largest surface of the
rectangular crystals is almost parallel to the crystallo-
¯
graphic ab plane. There are S···S and S···Se inter-
group P1. Crystal and refinement data are summa-
˚
molecular contacts of 3.594 and 3.610 A, respectively,
rized in Table 1. Fig. 1 shows the molecular struc-
ture and Fig. 2 shows a partially labelled plot of the
complex. The structure consists of centrosymmetric
slightly smaller than the sums of the van der Waals
radii (3.70 and 3.82 A, respectively), which give rise to
˚
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G. C. Papavassiliou et al. · Nickel 1,2-Dichalcogenolene Complexes as Single-component Semiconductors
681
Table 1. Crystal data and structure refinement for
Ni(dmeds)(dmit).
Empirical formula
Formula weight [g/mol]
Temperature [K]
C14H12Ni2S10Se4
934.10
293(2)
˚
Wavelength [A]
1.54180
monoclinic, P1
¯
Crystal system, space group
Unit cell dimensions
˚
a [A]
6.592(4)
8.236(4)
12.476(7)
˚
b [A]
˚
c [A]
α [deg]
87.91(2)
75.36(2)
74.49(2)
631.1(6)
1; 2.458
16.238
448
β [deg]
γ [deg]
3
˚
V [A ]
Z; calculated density [mg cm−3
]
Absorption coefficient [mm−1
F(000) [e]
]
Crystal size [mm3]
0.525×0.150×0.075
5.58 – 59.00
−6 ≤ h ≤ 0,
−9 ≤ k ≤ 8,
−13 ≤ l ≤ 13
1981/1799 (Rint = 0.039)
99.1 %
Fig. 2. Partially labeled plot of Ni(dmeds)(dmit) showing the
shortest S···S and Se···Se intermolecular interactions.
θ Range for data collection, deg
Limiting indices
Reflections collected/unique
Completeness to θ = 59.03
Absorption correction
Max./min. transmission
Data/restraints/parameters
Goodness-of-fit on F2
analytical
0.877/0.132
1799/0/140
1.068
Final R indices [I ≥ 2σ(I)]
R1 =0.0604, wR2 = 0.1615
R1 = 0.0616, wR2 = 0.1646
0.962 and −0.840
R Indices (all data)
−3
˚
Largest diff. peak and hole [e A
]
Fig. 3. Plots of resistivity versus the inverse temperature for
a single crystal of Ni(dmeds)(dmit) with currents approxi-
mately parallel (a) and perpendicular (b) to the ab plane.
Fig. 1. Molecular structure of Ni(dmeds)(dmit) with dis-
placement ellipsoids drawn at the 30 % probability level
(H-Atoms have been omitted for clarity). Primed atoms are
related to unprimed ones by the symmetry operation 1 − x,
−y, 1−z.
shows the inverse temperature dependence of the resis-
tivity obtained from single crystals of Ni(dmeds)(dmit)
with currents almost parallel to the ab plane (ꢀ) and
perpendicular to this plane (⊥). The r. t. conductivity
the formation of layers almost parallel to the ab plane values are σRT(ꢀ) = 1.5 ×10−5 S cm−1 and σRT(⊥) =
(Fig. 2). In other directions the contacts are larger. This 2.5 × 10−8 S cm−1. This means that the anisotropy is
indicates a quasi two-dimensional behavior of the ma- almost 103. The activation energy values were found
terial. Single crystals of the other complexes were not from the plots of Fig. 3 to be Eα(ꢀ) = 0.19 eV and
good enough for crystal structure determination. How- Eα (⊥) = 0.18 eV. The corresponding band gap (Eg =
ever, similar intermolecular interactions (S···Se and 2Eα) values are 0.38 and 0.36 eV. After a series of heat-
S···S contacts) are expected for these complexes.
ing/cooling cycles, the resistance in a number of crys-
Conductivity measurements on single crystals of tals decreased. Conductivity measurements on com-
Ni(dmeds)(dmit) showed an anisotropic behavior, in pressed pellets of Ni(dmeds)(dmit), Ni(dmedt)(dmit)
accordance with the crystallographic results. Fig. 3 and Ni(dpedt)(dsit) gave σRT(pellet) = 1×10−6, 1.2×
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682
G. C. Papavassiliou et al. · Nickel 1,2-Dichalcogenolene Complexes as Single-component Semiconductors
However, more improved techniques are required in
order to establish these new materials as semiconduc-
tor components of FETs. Also, NLO properties were
observed in some of these complexes, which are de-
scribed separately [5].
Experimental Section
(Dimethylethylenediselenolato)(1,3-dithiol-2-thione-4,5-
dithiolato)nickel, Ni(dmeds)(dmit)
In a two-necked 250 mL flask, a suspension of com-
pounds 1a (240 mg, 1 mmol) [11, 15] and 2 (406 mg,
1 mmol) [14, 17] in deoxygenated MeOH (10 mL) was pre-
pared. Then, a solution of NaOMe, freshly prepared from
Na (115 mg, 5 mmol) and MeOH (10 mL), was added un-
der nitrogen atmosphere and the mixture stirred for 30 min.
To the obtained red solution, a solution of NiCl2 · 6H2O
(238 mg, 1 mmol) in deoxygenated MeOH (30 mL) was
added dropwise within 15 min. The solution was stirred un-
Fig. 4. Plots of Id vs. Vd for several Vg values of a device
based on Ni(dcdt)(dmit).
10−7, and 1 × 10−7 – 5 × 10−6 S cm−1, respectively.
The Eg(pellet) values were found to be 0.45, 0.50– der nitrogen atmosphere for 1 h at r. t., whereupon the color
turned brown. Then, aq. HCl (2 mL, 35 %) was added and
the mixture was transferred to a beaker and stirred in air
overnight. The precipitate was washed with water and MeOH
and dried in air. The green-brown solid was extracted with
CS2 and chromatographed on silica gel, using CS2 as eluent.
The second green fraction contained Ni(dmeds)(dmit) (4 mg,
0.9 %). M. p. > 285 ◦C (dec.). – UV/vis/near IR (CS2): λmax
(lgεmax) = 950 nm (4.48). – IR (KBr): ν = 1056, 1073 (C=S),
2923 (CH3) cm−1. – C7H6S5Se2Ni (467.03): calcd. C 18.00,
H 1.28; found C 18.11, H 1.36.
0.80 and 0.46 eV, respectively. The σRT values of
Ni(dpedt)(dmit) and Ni(dcdt)(dmit) were found to be
very small (< 10−9 S cm−1).
The optical absorption (OA) spectra of thin de-
posits on quartz plates showed strong bands with max-
ima around 1.24 eV (1000 nm) and optical band gaps
(absorption edges) close to 0.7 – 0.8 eV. This means
that, in some complexes, the Eg values obtained from
resistivity measurements are smaller than those ob-
tained from the OA spectra of thin deposits (or solu-
tions). This is due to the fact that in compressed pel-
lets and/or single crystals the intermolecular interac-
tions are stronger than those in thin films (or solutions)
(see also [5, 6]).
All these air-stable complexes have the electrical
and optical features required for candidates for FETs
and NLO devices. Preliminary results of measure-
ments under the conditions of FETs were obtained
for Ni(dcdt)(dmit) thin deposits on Si-SiO2 substrates.
Fig. 4 shows the curves of drain current (Id) versus the
drain voltage (Vd) for several values of gate voltage
(Vg) of a device based on Ni(dcdt)(dmit). These curves
demonstrate the sensitivity of the channel (semicon-
ductor deposit) to the gate voltage. Several complexes
exhibit p-type as well as n-type conductance. The
Id-Vd curves obtained from Ni(dpedt)(dmit) were sim-
ilar to those obtained for Ni(dpedt)2, a material which
has been found to exhibit n-type conductance [21]. It
should be noticed that the best results were obtained for
(Dimethylethylenedithiolato)(1,3-dithiol-2-thione-4,5-
dithiolato)nickel, Ni(dmedt)(dmit)
Using 1b (162 mg, 1 mmol) [12, 13, 15], instead of 1a,
and 2 (406 mg, 1 mmol), the complex Ni(dmedt)(dmit) was
◦
obtained by the same procedure (9 mg, 2.4 %). M. p. 235 C
(dec.). – UV/vis/near IR (CS2): λmax (lgεmax) = 933 nm
(4.46). – IR (KBr): ν = 1048, 1064 (C=S), 2920 (CH3) cm−1
.
– C7H6S5Ni (373.25): calcd. C 22.52, H 1.61; found C 22.48,
H 1.56.
(Diphenylethylenedithiolato)(1,3-dithiol-2-thione-4,5-
diselenolato)nickel, Ni(dpedt)(dsit)
Using 3 (270 mg, 1 mmol) [13], instead of 1a, and 4
(500 mg, 1 mmol) [14, 16], instead of 2, the complex
Ni(dpedt)(dsit) was obtained by the same procedure (15 mg,
◦
2.5 %). M. p. 280 C (dec.). – UV/vis/near IR (CS2): λmax
(lgεmax) = 1005 nm (4.52). – IR (KBr): ν = 1039, 1048
(C=S) cm−1. – C17H10S5Se2Ni (591.13): calcd. C 34.54,
the complexes with the lower values of dc conductivity. H 1.69; found C 34.37, H 1.78.
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G. C. Papavassiliou et al. · Nickel 1,2-Dichalcogenolene Complexes as Single-component Semiconductors
683
(Diphenylethylenedithiolato)(1,3-dithiol-2-thione-4,5-
dithiolato)nickel, Ni(dpedt)(dmit)
every 97 reflections showed less than 3 % variation and no
decay. Lorentz, polarization and analytical absorption cor-
rections were applied using Crystal Logic software. Sym-
metry equivalent data were averaged with Rint = 0.0389
to give 1799 independent reflections from a total of 1981
collected. The structure was solved by Direct Methods us-
ing SHELXS-86 [22] and refined by full-matrix least-squares
techniques on F2 with SHELXL-97 [23] using 1799 reflec-
tions and refining 140 parameters. All hydrogen atoms were
introduced at calculated positions as riding on bonded atoms.
All non-hydrogen atoms were refined anisotropically. The
largest shift/esd in the final refinement cycle was 0.002.
Table 1 contains further numbers of the structure refine-
ment. CCDC 628860 contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free
of charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data request/cif.
Using 3 (270 mg, 1 mmol) [13], instead of 1a, and 2
(406 mg, 1 mmol), the complex Ni(dpedt)(dmit) was ob-
tained by the same procedure (104 mg, 21 %). M. p.
240 ◦C (dec.). – UV/vis/near IR (CS2): λmax (lgεmax) =
974 nm (4.65). – IR (KBr): ν = 1066, 1077 (C=S) cm−1
.
– C17H10S7Ni (497.35): calcd. C 41.05, H 2.01; found
C 40.92, H 1.93.
(1,2-Bis-decylsulfanyl-ethene-1,2-dithiolato)(1,3-dithiol-2-
thione-4,5-dithiolato)nickel, Ni(dcdt)(dmit)
Using 5 (462 mg, 1 mmol) [14], instead of 1a, and 2
(406 mg, 1 mmol), the complex Ni(dcdt)(dmit) was obtained
by the same procedure (5.5 mg, 0.8 %). M. p. 105 ◦C (dec.).
– UV/vis/near IR (CS2): λmax (lgεmax) = 1040 nm (4.54).
– IR (KBr): ν = 1064, 1072 (C=S), 2915 (CH3) cm−1
.
Physical measurements
– C25H42S9Ni (689.57): calcd. C 43.54, H 6.09; found
C 43.50, H 6.14.
Thin deposits on quartz plates and/or Si-SiO2 substrates,
with predefined interdigitated gold electrodes spaced 2 –
25 µm apart, were obtained by spinning, spraying or drop
casting solutions of the complexes in CS2. The OA spectra of
the complexes in CS2 or of thin deposits were recorded on a
Perkin-Elmer, model Lambda 19 spectrophotometer. The dc
conductivity was measured by the well known voltage-drive
method. The Id-Vd characteristics were measured by using a
4140B HP picoammeter.
X-Ray crystal structure determination
A suitable single crystal was mounted in air and
diffraction measurements were made on a P21 Nicolet
diffractometer upgraded by Crystal Logic using graphite-
monochromated CuKα radiation. Crystal data and other
numbers pertinent to the structure determination are col-
lected in Table 1. Unit cell dimensions were determined and
refined by using the angular settings of 25 automatically cen-
tered reflections in the range 22 < 2θ < 54◦. Intensity data
were recorded using θ-2θ scans to 2 θmax = 118◦, with a
scan speed of 4.5 deg min−1 and a scan width of 2.45◦
plus α1α2 separation. Three standard reflections monitored
Acknowledgement
The work was carried out as a part of the “Excellence
in the Research Institutes” project grant 0684, supported by
GSRT/Ministry of Development in Greece.
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