Electrochemical Investigations of Tripyrrin Complexes

Journal of Porphyrins and Phthalocyanines
Published at http://www.u-bourgogne.fr/jpp/
J. Porphyrins Phthalocyanines 2003; 7: 220-226

N
M
N
Electrochemical investigations of tripyrrin complexes

Jordi Bley-Escricha, Serguei Prikhodovskib, Carsten D. Brandtb, Martin Brringb
and Jean-Paul Gisselbrecht*a
Laboratoire dElectrochimie et de Chimie Physique du Corps Solide, UMR 7512 - CNRS Universit Louis
Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg, France
b
Philipps-Universitt Marburg, FB Chemie, Hans-Meerwein-Strasse, D-35032 Marburg, Germany
J. Porphyrins Phthalocyanines 2003.07:220-226. Downloaded from www.worldscientific.com

by INDIAN INSTITUTE OF TECHNOLOGY on 12/26/14. For personal use only.
Received 15 May 2003

Accepted 30 May 2003
ABSTRACT: Electrochemical investigations on divalent transition metal complexes with a
conjugated linear tripyrrole ligand, namely 3,4,8,9,13,14-hexaethyl-2,15-dimethyltripyrrin (HTrpy)
are reported. This tripyrrin ligand behaves as a tridentate monoanionic ligand and forms a series
of neutral metal complexes of the type TrpyMX, where M = Zn(II), Cu(II), Ni(II) Co(II) or Pd(II)
and X is a chloride anion (Cl-). The studied nickel, cobalt and zinc complexes undergo respectively
three and two ligand-centered reversible one-electron reductions and a reversible ligand-centered
one-electron oxidation. Only irreversible electron transfers are observed for TrpyPdCl, due to the
instability of the reduced complex. TrpyCoCl does not undergo any metal-centered electron transfer
which is unexpected compared to related complexes. The copper(II) complex shows an additional
reduction step occurring on the metal, generating a stable copper(I) complex. A comparison of the
redox behavior of tripyrrin complexes with porphyrins and linear tetrapyrrolic complexes, namely
bidipyrrins, clearly indicates that the observed redox behavior of tripyrrin complexes is mainly metal
dependent. The observed HOMO-LUMO gap in the studied series of tripyrrins is rather small (about
1.70 V) compared to porphyrins (2.25 V), but it is close to bidipyrrins (1.60 V). Copyright 2003
Society of Porphyrins & Phthalocyanines.
KEYWORDS: transition metal complexes, N ligands, electrochemistry, tripyrrins.
INTRODUCTION
Among the open-chain polypyrroles, tetrapyrroles
have been studied quite extensively over several
decades as this class of chromophores derives mainly
from natural bile pigments [1]. Tripyrroles have been
extensively used as intermediates in the synthesis of
porphyrins [2] and expanded porphyrins [3]. Even
though tripyrroles have been well known for over
twenty years [4, 5], reports of their transition metals
complexing capabilities have remained scarce in the
literature and only several complexes like I to IV (Fig.
1) have been obtained [5-10]. The copper tripyrrene
complex III [1], the copper tripyrrane complex II
[8] and the tripyrrinone complexes IV [10] have
*Correspondence to: Jean-Paul Gisselbrecht, email:
gissel@chimie.u-strasbg.fr, fax: +33 3 90 24 14 31
Copyright 2003 Society of Porphyrins & Phthalocyanines
been structurally characterized. Nevertheless,

electrochemical studies on tripyrroles are rare
and, to our knowledge, only the electrochemistry
of a copper(II) tripyrrane complex II [8] has been
published. This free-base tripyrrane behaves as a
dianionic ligand forming a neutral complex with
copper(II) and the electrochemical investigations
clearly show that copper(I) could be stabilized in this
complex.
More recently, studies on the coordination
chemistry of tripyrrin have been carried out and
allowed an identification of a whole series of divalent
transition metal complexes [11-14] whose structures
V are shown on Fig. 1. In the present paper we present
the first electrochemical investigations on tripyrrin
complexes, namely TrpyZnCl, TrpyCuCl, TrpyNiCl,
TrpyCoCl and TrpyPdCl. The aim of the present
TRIPYRRIN COMPLEXES
OH
OH
O
N
N
N
M
O
NC
Et
Bn
Bn
M = H2, Cu(II), Co(II), Zn(II)
M = H2, Ni(II)
II
Ar
Ar
N
N
Cu

COCF3
O
O
Ar
OEt
M = H2, Cu(II), Zn(II),

Ni(II), Pt(II), Pd(II),
IV
III
N
N
N
N
M
R
N
R
N
X
M = Zn(II), Ni(II),
Cu(II), Co(II), Pd(II)
X = Cl
R = H, Ph
M = H2, Ni(II), Pd(II), Cu(II)
VI
Me
Ph
Ph
I
N
Ph
C CH
3
Cu
Ph
CH3
N
Ph
Cu
N
Ph
N
Cl
Ph
Ph
VII
VIII
Fig. 1. Structure of some known tripyrrolic and

tetrapyrrolic complexes: I [5], tripyrrane complexes II [8],
tripyrene complex III [1], tripyrrinone complexes IV [9,
10], tripyrrin complexes V [11-14], bidipyrrin complexes
VI [15, 16], inverted porphyrin complex VII [22] and Nsubstituted porphyrin complex VIII [23]
study is to obtain insights into the electrochemical

behavior of this new class of complexes for which
no data has been published before and to compare
the observed electrochemical behavior to both
previously studied tripyrroles and to open and closed
tetrapyrroles like bidipyrrin complexes VI (Fig. 1)
[15, 16], bilindione [17-19], formylbiliverdin [20],
porphyrin [21], inverted porphyrin VII [22] and Nsubstituted porphyrin complexes VIII [23] for which
electrochemical data are available.
221
EXPERIMENTAL
All solvents used for synthetic purposes were
dried using a standard procedure and stored in the
dark under an argon atmosphere. The tripyrrin
complexes were prepared as described previously
for TrpyPdCl [12] and TrpyNiCl(OH2) [13]. The new
TrpyCoCl, TrpyCuCl and TrpyZnCl complexes were
obtained from the respective trifluoroacetates [14] by
treatment with aqueous sodium chloride. Reagents
and materials for chromatography were purchased
from Aldrich, Strem, ABCR or Merck and used as
received. NMR spectra were obtained with a Bruker
AMX 400 spectrometer in the solvents indicated
below. Chemical shifts () are given in ppm relative
to TMS. Mass spectra (EI, 70 eV) were recorded on
a Finnigan 90 MAT instrument. m/z values are given
for the most abundant isotopes only. Melting points
were measured by DTA on a Thermoanalyzer DuPont
9000. Elemental analyses (C, H, N) were carried out
at the microanalytical laboratory of the Institut fr
Anorganische Chemie, Universitt Wrzburg.
Chloro-(3,4,8,9,13,14-hexaethyl-2,15-dimethyltripyrrinato)cobalt(II). TrpyCoCl. Yield: 99%. mp
98 C (decomp.). 1H NMR (CD2Cl2, 295 K): , ppm
1.41 (s, 6H), 7.94 (s, 2H), 9.98 (s, 6H), 15.86 (s, 6H),
16.81 (s, 2H), 19.66 (s, 2H), 22.61 (s, 2H), 24.41 (s,
2H), 35.83 (s, 6H), 53.04 (s, 2H), 59.40 (s, 2H). EIMS: m/z 510 [M]+. [C28H38ClN3Co, 511.02]: calcd.
C 65.81, H 7.50, N 8.22, found: C 65.58, H 7.56, N
8.18.
Chloro-(3,4,8,9,13,14-hexaethyl-2,15-dimethyltripyrrinato)copper(II). TrpyCuCl. Yield: 73%. mp
80 C (decomp.). EI-MS: m/z 515 [M]+, 479 [M-Cl]+.
[C28H38ClN3Cu, 515.63]: calcd. C 65.22, H 7.43, N
8.15, found: C 64.99, H 7.47, N 7.93.
Chloro-(3,4,8,9,13,14-hexaethyl-2,15-dimethyltripyrrinato)zinc(II). TrpyZnCl. Yield: 79%. mp
172 C. 1H NMR (CDCl3, 295 K): , ppm 1.14 (t,
6H), 1.20 (t, 6H), 1.24 (t, 6H), 2.42 (q, 4H), 2.60
(q, 4H), 2.62 (q, 4H), 2.67 (s, 6H), 6.86 (s, 2H). 13C
NMR (CDCl3, 295 K): , ppm 13.8, 15.9, 16.2, 16.5,
16.6, 16.8, 17.1, 118.7, 133.9, 137.6, 142.1, 142.2,
148.2, 169.3. EI-MS: m/z 515 [M]+, 479 [M-Cl]+.
[C28H38ClN3Zn, 517.63]: calcd. C 64.97, H 7.40, N
8.12, found: C 64.72, H 7.42, N 8.05.
The electrochemical measurements were carried
out in a glove box (less than 3 ppm of H2O and less
than 2 ppm of O2) at room temperature (25 2 C)
in PhCN containing 0.1M Bu4NPF6 using a classical
three electrode cell. The electrochemical cell was
connected to a PAR 362 potentiostat driven by a
PowerLab interface (ADInstruments) controlled by
the E-Chem software (ADInstruments) running on a
PC computer. The working electrode was a platinum
(Pt) disk electrode (diameter: 2 mm) used either
motionless for cyclic voltammetry (v = 20 mV/s to

222
J. BLEY-ESCRICH ET AL.
5 V/s) or as a rotating disk electrode. The auxiliary

electrode and the pseudo-reference electrode were
platinum wires. All potentials are referred to the
ferrocenenium/ferrocene (Fc+/Fc) couple used as
internal standard.
Benzonitrile (PhCN, Aldrich, 99%) was dried,
before use, for two days with CaCl2 (anhydrous,
Fluka, 97%), and distilled on P2O5 (Prolabo) under
a reduced pressure and an inert atmosphere (Argon).
The main fraction was collected under argon and
transferred into the glove box. The supporting
electrolyte, Bu4NPF6 (Fluka - electrochemical grade)
was dried in an oven (65 C) under vacuum for two
days. Bu4NPF6 was solubilized in PhCN inside the
glove box and the solution was then percolated over
activated aluminia. The available potentials on a
platinum working electrode ranged from -2.5 to +1.8
V vs. Fc+/Fc.
Spectroelectrochemical
measurements
were
carried out in PhCN in a home-made quartz cell,
having an optical pathlength of 1 mm. The working
electrode was a platinum grid (1000 mesh) placed
in the optical pathlength. The reference and the
auxiliary electrodes were platinum wires in individual
compartments separated from the solution by cotton.
The cell was filled in the glove box and hermetically
closed, after which it was placed in a diode array
spectrophotometer (Hewlett-Packard 8453) and
spectra were recorded during electrolysis.
and nickel complexes as shown in Fig. 3 whose

redox potentials are summarized in Table 2. Peak
characteristics evolutions with scan rates confirm
the reversibility of the different electron transfers.
Indeed, Ip = f(v1/2) was linear and crossed the
origin of the axis, the peak current ratio Ipa/Ipc was
unity at all sweep rates and the peak potentials
remained constant up to 1 V.s-1. However, careful
examination of the first oxidation peak shape for
the copper and nickel complexes show a shoulder
of small amplitude. Due to the close proximity of
RESULTS AND DISCUSSION

Electrochemical investigations by rotating disk
voltammetry and cyclic voltammetry
Fig. 2. Rotating disk voltammograms of the tripyrrin

complexes in the presence of added ferrocene on a platinum
disk (N = 2000 rpm) in PhCN + 0.1M Bu4NPF6
Electrochemical investigations were carried out

in benzonitrile containing tetrabutylammonium hexafluorophosphate (0.1M) as
Table 1. Half-wave potentials obtained by rotating disk voltammetry
supporting electrolyte. The zinc, nickel,
(RDV) in PhCN + 0.1M Bu4NPF6 on a Pt rotating disk electrode
cobalt and the copper complexes give well
(N = 2000 rpm) and, in parenthesis, the wave slopes in mV and the
resolved waves of similar amplitudes by
limiting current ratio R = Ilim stepX/Ilim Red1
rotating disk voltammetry (RDV) (Fig. 2).
Compound E1/2Red3a
E1/2Red2a
E1/2Red1a
E1/2Ox1a
E1/2Ox1a
The palladium complex gives three reduction
waves, the second reduction at -1.68 V vs.
TrpyZnCl
-2.13
-1.41
+0.45
+1.53
Fc+/Fc being of small amplitude. Also a
(117, 1)
(83, 1)
(97, 1)
(205, 1)
small amplitude wave at + 0.61 V vs. Fc+/
TrpyNiCl
-2.28
-1.63
-1.29
+0.26
Fc is observed after the first oxidation. All
(71, 1)
(64, 1)
(77, 1)
(64, 1)
data are collected in Table 1. Wave analysis,
TrpyCuCl
-2.22
-1.59
-1.00
+0.43
using the Tome criteria [24], give slopes
(67, 1)
(61, 1)
(95, 1)
(61, 1)
close to 65 mV, except for the first reduction
TrpyCoCl
-2.00
-1.30
+0.40
+0.61
step of the copper complex for which a slope
(77, 0.9) (71, 1) (77, 0.9) (- , 0.2)
of 95 mV is observed. The observed slopes
TrpyPdCl
-2.16
-1.68
-1.34
+0.37
+0.61
are close to the 56.4 mV, expected for a
(97,
0.9)
(58,
0.4)
(71,
1)
(64,
1)
(78,
0.14)
reversible one-electron transfer.
a
Cyclic voltammetry gives well defined
Half-wave potentials in volts versus ferrocene, used as internal
cyclic voltammograms for the zinc
standard.
TRIPYRRIN COMPLEXES

these two oxidations, a detailed analysis could not

be carried out. Nevertheless, this behavior looks like
the oxidation of the cobalt complex, for which, these
two steps are well resolved. The cobalt complex also
gives two reversible reduction steps. Oxidation at low
scan rates shows two reversible electron transfers,
the second being of small amplitude. The peak
characteristic evolution with scan rates clearly shows
that the second oxidation step vanishes at scan rates
higher than 10 V/s. These results indicate that the
second oxidation step involves an electrogenerated
species obtained after the first oxidation. This
223
mechanism also explains why the second oxidation

step, observed by rotating disk voltammetry (Fig.
2) is of small amplitude. For the copper complex,
the first oxidation as well as the second and the
third reductions are reversible electron transfers. In
contrast, the first reduction of TrpyCuCl is irreversible
as shown by the cathodic peak potential shift towards
more negative potentials with increasing scan rates.
The reduction peak potential is observed at -1.01 V
vs. Fc+/Fc (v = 0.1 V.s-1) whereas, on the reverse scan,
the reoxidation peak is observed at -0.54 V vs. Fc+/Fc.
Such a large potential difference seems characteristic
of an electron transfer occurring on the copper and
followed by a significant geometric rearrangement,
as observed previously for quaterpyridine copper
complexes [25]. The palladium complex, in contrast
to the above behavior, gives only irreversible electron
transfers, which means that the generated species are
unstable under our experimental conditions.
Spectroelectrochemical investigations
Investigation of TrpyZnCl. Due to the instability

of the free-base derivative, the zinc complex was
used as a reference to assign electron transfer sites,
zinc being a non-electroactive metal. Oxidation on
the plateau potential of the first oxidation gives rise to
well-defined spectral evolutions (Fig. 4). The initial
bands at 357, 624 (sh) and 670 nm decrease whereas
new bands appear at 470 and 499 nm. Reduction of
the electrogenerated species leads to a restoration
of the initial spectrum. The regeneration is not
quantitative but more than 90% of the initial species
can be recovered.
Reduction on the plateau potential of the first
reduction step gave spectral evolutions with welldefined isosbestic points. The initial bands at 357,
Fig. 3. Cyclic voltammograms of the tripyrrin complexes
625 and 670 nm decrease, whereas new bands at
in the presence of added ferrocene on a platinum disk (v =
394, 513, 687, 832, 918 and 1028 nm appear. The
0.1V.s-1) in PhCN + 0.1M Bu4NPF6
presence of low energy absorption bands at 918
and 1028 nm, seems characteristic for the
generation of a radical anion as observed
Table 2. Electrochemical data obtained by cyclic voltammetry (v =
0.1V.s-1) in PhCN + 0.1M Bu4NPF6 on a Pt working electrode
for porphyrins and porphyrin isomers.
Re-oxidation of the electrogenerated
Compound ERed3a ERed2a ERed1a
EOx1a
EOx1a
species gives back quantitatively the initial
spectrum, indicative of good stability of the
TrpyZnCl
-1.87
-1.37
+0.42
+1.49b
electrogenerated species.
b
TrpyNiCl
-2.23
-1.61
-1.27
+0.36
+1.51
Electrolysis carried out on the second
TrpyCuCl
-2.20
-1.58
-1.01b, c
+0.41
reduction step shows that the low energy
bands vanish whereas the bands at 513 and
TrpyCoCl
-1.92
-1.28
+0.39
+0.64c
570 nm increase. Stepwise re-oxidation of
TrpyPdCl
-2.16b, d -1.64b, e
-1.35b
+0.45b
+0.61e
the dianion does not regenerate the initial
spectrum quantitatively. The band observed
a
Formal redox potential in volts versus ferrocene, used as internal
during the second reduction step at 513 nm
b
-1
standard: E = (Epa + Epc)/2. Peak potential at v = 0.1V.s for
remains whereas the observed bands at 357
irreversible electron transfers. c An anodic peak potential is observed
and 677 nm are reminiscent of the initial
at -0.54V vs. Fc+/Fc on the reverse scan. d A fourth irreversible peak
is observed at -2.31V vs. Fc+/Fc. e Small amplitude signal.
species. One part of the generated doubly

224
new bands at 345, 489, 608 659 and 708 nm increase.

During the first reduction, bands at 360, 389, 520,
626, 655, 835 and 913 nm are observed. The spectral
evolutions are quite similar to those observed for the
zinc complex indicative of a ligand centered electron
transfer. The generated radical anion is stable and can
be reoxidized quantitatively to its neutral complex,
whereas the generated radical cation, obtained during
oxidation, undergoes a partial decomposition. Indeed
reductive electrolysis regenerates only about 60 to
70% of the initial material.
Spectral investigations of the palladium complex
confirm the irreversibility of the electron transfers
observed by cyclic voltammetry for the oxidation.
Indeed, the initial bands at 362, 650 (sh) and 693 nm
decrease during oxidation and new bands at 362, 414,
471, 507, 680 (sh) and 693 nm are observed. However
the initial species cannot be recovered by reduction of
the oxidized species. The reduction deserves special
attention. Electrolysis carried out on the plateau
potential of the first reduction gives nice spectral
evolutions and new bands at 359, 393, 554 and
691 nm are observed. Comparison with the spectral
evolutions of the zinc complex shows a spectral
pattern similar to that observed for the dianion with
a strong absorption band at 554 nm. Despite its
irreversible behavior by CV, the electrogenerated
species can be quantitatively oxidized to the initial
TrpyPdCl. Further investigations are under way to
explain this behavior.
Fig. 4. Time resolved UV-vis spectra for TrpyZnCl in

PhCN + 0.1M Bu4NPF6. First oxidation step (A), first (B)
and second (C) reduction steps
reduced compound undergoes partial decomposition,

giving rise to the band at 513 nm. The latter species
cannot be oxidized.
In conclusion, the generated radical anion is a
stable species, whereas the radical cation and the
dianion undergo a partial decomposition under our
experimental conditions.
Investigation of TrpyCoCl, TrpyPdCl and
TrpyNiCl. The TrpyCoCl and TrpyNiCl complexes
gave spectral evolutions with well-defined isosbestic
points. For TrpyCoCl the bands at 359, 403, 431 and
694 nm vanish during oxidation whereas new bands
at 470 (sh), 492 and 607 nm increase. During the first
reduction, new bands at 388, 571, 665 and 880 nm are
observed. For the nickel complex, the bands at 355,
412, 619 (sh) and 656 nm vanish during oxidation and
Investigation of TrpyCuCl. TrpyCuCl gives nice

spectral evolutions with well-defined isosbestic
points during both oxidation and the three reductions.
The spectral evolutions are reported in Fig. 5. For the
first oxidation the spectral evolutions are similar to
those observed for the first oxidation of TrpyZnCl.
This behavior is characteristic of a ligand centered
oxidation.
For the first reduction, the band at 357 nm
remains unchanged whereas the bands at 613 (sh)
and 660 nm decrease during reductive electrolysis
with concomitant increase of a new band at 712
nm. In addition, small bands at 431 and 523 nm
are observed for the one-electron reduced species.
Further reduction on the plateau potential of the
second reduction step gives also drastic spectral
modifications. The two electron reduced species
possesses bands at 402, 521, 676, 808, 896 and 1006
nm. The latter low energy bands are characteristic for
the generation of a radical anion. Comparison of the
latter spectrum to that of the one-electron reduced
TrpyZnCl complex (bands at 394, 513, 687, 832,
918 and 1028 nm) shows large similarities between
both spectra, which is indicative of a ligand centered
reduction, generating a radical anion during this
second reduction. From these data it is clear that the
TRIPYRRIN COMPLEXES
225
similar to those observed for the second reduction

of TrpyZnCl. Indeed, the bands observed for the
direduced species vanish whereas new bands at 413,
523, 590(sh) and 632 nm are observed.

Discussion
Fig. 5. Time resolved UV-vis spectra for TrpyCuCl in

PhCN + 0.1M Bu4NPF6. First oxidation step (A), first (B),
second (C) and third (D) reduction steps
first reduction is metal centered, whereas the second

reduction is ligand centered generating a copper(I)
radical anion. The latter species have been stepwise
reoxidized quantitatively to the initial species. The
generated species are therefore stable under our
experimental conditions. Electrolysis carried out
on the third reduction wave gives spectral changes
The observed results clearly demonstrate that

the examined tripyrrin complexes, except for
TrpyCuCl, undergo one ligand-centered oxidation
as well as two ligand-centered reductions. TrpyCoCl
does not undergo any metal-centered oxidations
or reductions which is quite unusual compared to
porphyrins. In addition the tripyrrin ligand, which
indeed is a monoanion, is able to stabilize copper(I)
as shown by spectroelectrochemical investigations.
For the examined complexes, the oxidation and
reduction potentials do not follow any correlation
with the metal characteristics, namely ionic radii
or electronegativity. It seems that geometric factors
are responsible for the observed electrochemical
behavior, which is, to some extent, expected due to
the flexibility of this tripyrrin ligand. However due
to the limited number of examined complexes no
definitive conclusion can be drawn from the present
study. Especially the potential difference E = Eox1 Ered1 is not constant for the studied series of complexes
and spans a range from 1.63 to 1.79 V. The observed
average value of 1.70 V is much smaller than for
porphyrins (2.25 V) and close to bidipyrrins (1.60
V). Spectroelectrochemical studies clearly indicate
that the stability of the electrogenerated species
(radical cation and dianion) is much lower than for
previously characterized complexes of porphyrins,
or bidipyrrins [15, 16]. The stability of the oxidized
and reduced species is even lower for the palladium
complex for which only irreversible electron transfers
can be observed by cyclic voltammetry. In contrast
to porphyrins, bilindiones [18, 19], formylbiliverdin
[20] and bidipyrrin, tripyrrin is able to stabilize
copper(I). Such stabilization is in agreement with
the monoanionic character of the tridentate tripyrrin
ligand. As mentioned in the introduction, only one
example of copper(I) stabilization by a tripyrrane has
been observed in the literature and this was reported
by Sessler et al. [8]. From literature data, copper(I)
can only be stabilized in some cyclic tetrapyrrolic
complexes like inverted porphyrins [22] and for some
N-substituted porphyrins [23]. In these complexes,
only three pyrroles of the ligand are coordinated to
the copper, like in tripyrrin.
CONCLUSION
The present electrochemical investigation of
tripyrrin complexes containing divalent transition
metals clearly demonstrates that the examined zinc,

226
cobalt, nickel and palladium complexes undergo

ligand-centered electron exchanges whereas in the
case of the copper complex, reduction of the copper
generates a stable copper(I) complex with the tripyrrin
ligand. Even the electron transfers are reversible
by cyclic voltammetry, except for the palladium
complex, spectroelectrochemical investigations show
that only the generated radical anion is stable whereas
the radical cation as well as the dianion undergo partial
decomposition. Such a behavior is quite different
compared to previously studied bidipyrrin complexes
and porphyrins for which the generated species
remain stable under similar experimental conditions.
Further investigations are necessary to obtain more
information about the stability of tripyrrin complexes
by changing the nature of the coordinated anion and
to investigate how these changes may affect the redox
behavior and the stability of the electrogenerated
species for this new class of complexes.
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Journal of Porphyrins and Phthalocyanines

J. Porphyrins Phthalocyanines 2003; 7: 220-226