Mono- and di-nuclear 2,3-diazabutadiene and 2-azabutadiene complexes of Rhenium(I): Syntheses, luminescence spectra and X-ray structures

Article abstract of DOI:10.1016/j.inoche.2008.05.022

Treatment of [Re(CO)₃(THF)(μ-Br)]₂ with 4,4-dichloro-1,1-diphenyl-2-azabuta-1,3-diene [Cl₂C{double bond, long}C(H)-N{double bond, long}CPh₂] (1a) yields the di-nuclear benzophenone azine-bridged compound [(OC)

Full text of DOI:10.1016/j.inoche.2008.05.022

Inorganic Chemistry Communications 11 (2008) 1060–1063
Contents lists available at ScienceDirect
Inorganic Chemistry Communications
journal homepage: www.elsevier.com/locate/inoche
Mono- and di-nuclear 2,3-diazabutadiene and 2-azabutadiene complexes
of Rhenium(I): Syntheses, luminescence spectra and X-ray structures
b
Rodolphe Kinghat a, Abderrahim Khatyr a, Gerard Schmitt a, Michael Knorr a, , Marek M. Kubicki ,
*
Estelle Vigier b, Fernando Villafañe c
a Institut UTINAM UMR CNRS 6213, Université de Franche-Comté, Faculté des Sciences et des Techniques, 16, Route de Gray, 25030 Besançon, France
b Institut de Chimie Moléculaire de l’Université de Bourgogne, UMR CNRS 5260, Faculté des Sciences et des Techniques, 9, Av. Alain Savary, 21078 Dijon, France
c IU CINQUIMA, Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain
a r t i c l e i n f o
a b s t r a c t
Article history:
Treatment of [Re(CO)3(THF)(
CPh2] (1a) yields the di-nuclear benzophenone azine-bridged compound [(OC)3Re(
l
-Br)]2 with 4,4-dichloro-1,1-diphenyl-2-azabuta-1,3-diene [Cl2C@C(H)–N@
-Ph2C@N–N@CPh2)-
-Ph2C@N–N@CPh2)( -X)2-
Re(CO)3] (2a,b) (X = Br, Cl) are obtained in high yields by direct reaction of [Re(CO)3(THF)( -Br)]2 or
[Re(CO)5Cl] with benzophenone azine. Nucleophilic attack of NaSPh on 1a affords the 2-azabutadiene
derivative [(PhS)(Cl)C@C(H)–N@CPh2] (1b), which upon reaction with [Re(CO)3(THF)( -Br)]2 forms the
Received 29 March 2008
Accepted 21 May 2008
Available online 27 May 2008
l
(
l
-Br)2Re(CO)3] (2a), albeit in low yield. Alternatively, compounds [(OC)3Re(
l
l
l
Keywords:
l
2-Azabutadiene
2,3-Diazabutadiene
Azine
S,N-chelate complex fac-[(OC)3ReBr{(PhS)(Cl)C@C(H)–N@CPh2}] (3). The crystal structures of 1b, 2a
and 3 have been determined and the luminescence properties of 2 and 3 have been investigated.
Ó 2008 Elsevier B.V. All rights reserved.
Thioether
Rhenium
Luminescence
Apart from their application in homogenous catalysis [1–4],
transition metal complexes chelated by 1,4-diazabutadiene (dii-
mine) ligands are studied experimentally and theoretically by
numerous research groups due to their interesting photophysical
properties. In particular, the rich photophysics of Re(I) compounds
have been the subject of many articles [5–12]. In continuation in
our work on the organic and coordination chemistry of 2-azabutadi-
ene compounds [13], we have recently exploited the reactivity of
the vinyl-chlorine bonds of [Cl2C@C(H)–N@CPh2] (1a) for oxidative
addition reactions across low-valent metal centers to synthesize
have not investigated in detail the mechanism of the scission of
1a, and the nature of the other products formed in this reaction.
We suppose that cleavage of 1a may account for in situ formation
of benzophenone azine, which then coordinates on [Re(CO)3(THF)-
(l-Br)]2. Indeed, [(OC)3Re(l-Ph2C@N–N@CPh2)(l-Br)2Re(CO)3]
(2a) is also accessible in 81% yield by addition of independently
prepared benzophenone azine to [Re(CO)3(THF)(l-Br)]2 in a 1:1
ratio according Scheme 1.
As evidenced by an X-ray diffraction study, the di-nuclear bro-
mide-bridged core motif of the precursor complex [14c] is also
found in the solid-state structure of 2a (Fig. 1).1 The asymmetric unit
of monoclinic lattice contains one di-nuclear complex molecule and
one CH2Cl2 solvent molecule. The molecular structure of 2a is quite
r-alkenyl complexes trans-[MCl{(C(Cl)@C(H)–N@CPh2)}(PPh3)2]
(M = Pd, Pt) possessing a -conjugated organic array [13c]. Further-
p
more, the functionalisation of 1a by two thioether groups gives rise
to polydentate ligand systems, thus allowing the preparation of
cyclometallated Pd and Pt C,N,S-pincer complexes [13d].
With the objective to synthesize some rhenium complexes
ligated by these 2-azabutadiene ligands for luminescence studies,
similar to a series of complexes of the type [(OC)3Re(l-E-E)(l-Br)2-
Re(CO)3] (E = SPh [15a], SMe [15b], SePh [15c], TePh [15d], PPh2
[15e], SbPh2 [15f]). The structure consists of two pseudo-octahedral
Re(I) centers joined by a common Brꢀ ꢀ ꢀBr edge and a N–N azine
bridge. Three last sites on each Re atom are occupied by terminal
CO ligands in fac-geometry. The dihedral angle in the Re(1)–N(1)–
N(2)–Re(2) zigzag array amounts to 32.9(4)°. In the butterfly-like core
we reacted [Re(CO)3(THF)(l-Br)]2 [14a,14b] with two equivalent
of 1a. Unfortunately, the outcome of the reaction was not straight-
forward and gave a mixture of several products. We succeeded to
isolate by recrystallisation from CH2Cl2/heptane in a low yield of
just 16% yellow air-stable crystals of the di-nuclear azine-bridged
1
compound [(OC)3Re(l-Ph2C@N–N@CPh2)(l-Br)2Re(CO)3] (2a). We
Crystal data for 2a (115(2) K) C33H22Br2Cl2N2O6Re2:Mr = 1145.65, mono-
clinic, P21/c, a = 17.5465(3) Å, b = 11.1189(2) Å, c = 18.9674(4) Å, b = 112.608(1)°, V =
3416.1(1) Å3,
l
= 9.623 mmꢁ1
,
Z = 4; d = 2.228 g/cm3, Mo
K
a
= 0.71073 Å, Nonius
Kappa CCD; structure refined by full-matrix least-squares on F2 to give final indices
1 = 0.0343 and wR2 = 0.0760; GOF = 1.046.
* Corresponding author. Tel.: +33 3 81 66 62 70; fax: +33 3 81 66 64 38.
E-mail address: michael.knorr@univ-fcomte.fr (M. Knorr).
R
1387-7003/$ - see front matter Ó 2008 Elsevier B.V. All rights reserved.
doi:10.1016/j.inoche.2008.05.022

R. Kinghat et al. / Inorganic Chemistry Communications 11 (2008) 1060–1063
1061
Ph
O
C
Ph
THF
C
C
Ph
Ph
CO
CO
Br
Br
OC
OC
N
N
2 equiv. 1a
OC
CO
Re
Re
+ ?
CH2Cl2
- THF
Br
Br
Re
Re
OC
CO
C
O
THF
C
C
O
O
2a
Ph
Ph
CH2Cl2
- THF
C
C
Ph
[Re(CO)3(THF)(μ-Br)]2
Ph
N
N
OC
CO
Ph2C=N-N=CPh2
X
X
Re
Re
OC
CO
CHCl3
- CO
2 [Re(CO)5Cl]
C
C
O
O
2a X = Br
2b X = Cl
Scheme 1.
Cl
H
N
H
Cl
NaSPh
3
C
2
C
C
C
Ph
Ph
Ph
Ph
1
DMF
Cl
Ph
C
S
C
N
- NaCl
1a
1b
Ph
Ph
C
Br
1b
N
OC
H
C
C
0.5 [Re(CO)3(THF)(μ-Br)]2
Re
CH2Cl2
- THF
OC
S
C
O
Cl
Ph
3
Scheme 2.
does not hold for l-Se2Ph2 complex, but the X-ray structure is of quite
poor quality [15c]. Compared with the N–N bond distance of uncoor-
dinated benzophenone azine, that of 2a is somewhat elongated
(1.402(12) Å vs. 1.447(6) Å); in contrast, the C@N imine bonds
(1.287(9) Å vs. 1.302(7) Å) remain equal within the standard devia-
tion [16].
Fig. 1. View of the molecular structure of 2a. Selected bond lengths [Å] and angles
[°]: Re(1)ꢀ ꢀ ꢀRe(2)3.6958(3), Br(1)ꢀ ꢀ ꢀBr(2) 3.4935(8), Re(1)–Br(1) 2.6090(6), Re(1)–
Br(2) 2.6379(6), Re(2)–Br(1) 2.6351(6), Re(2)–Br(2) 2.6413(6), Re(1)–N(1) 2.253(4),
Re(2)–N(2) 2.272(4), Re(1)–C(1) 1.900(6), Re(1)–C(2) 1.903(6), Re(1)–C(3) 1.908(6),
Re(2)–C(4) 1.910(6), Re(2)–C(5) 1.921(6), Re(2)–C(6) 1.923(6), N(1)–N(2) 1.447(6),
N(1)–C(7) 1.305(7), N(2)–C(20) 1.299(7); Re(1)–Br(1)–Re(2) 89.62(2), Re(1)–Br(2)–
Re(2) 88.86(2), Br(1)–Re(1)–Br(2) 83.49(2), Br(1)–Re(2)–Br(2) 82.92(2),
N(1)–Re(1)–Br(1) 85.9(1), N(1)–Re(1)–Br(2) 78.4(1), N(2)–Re(2)–Br(1) 77.6(1),
N(2)–Re(2)–Br(2) 85.6(1), Re(1)–N(1)–N(2) 117.1(3), Re(2)–N(2)–N(1) 117.3(3).
The chloro-bridged derivative [(OC)3Re(
l-Ph2C@N–N@CPh2)-
(l-Cl)2Re(CO)3] (2b) was isolated as a yellowish crystalline solid
after heating a CHCl3 solution of [Re(CO)5Cl] with benzophenone
azine.2 Note that reports on metal complexes with benzophenone
azine as ligand are quite scarce [17]. One rare example is the com-
plex cis-[Pt(C6F5)2(
azine acting as monodentate ligand [18]. This bonding mode has also
g
1-Ph2C@N–N@CPh2)(CO), with benzophenone
been structurally evidenced for [(C6F5)Au(
[19].
g
1–Ph2C@N–N@CPh2)]
formed by two equatorial ReBr2(CO)2 seven-atom planes with shared
Br1/Br2 edge the dihedral (folding) angle is equal to 37.0(1)°. When re-
stricted to the four heavy atoms (Re, Br), this angle reaches 40.12(2)°.
This is the largest folding angle observed in this di-nuclear family
Functionalization of azabutadiene 1a by addition of 1.2 equiva-
lent of sodium thiophenolate in dry DMF leads under mild condi-
tions in
a stereospecific manner to the thioether derivative
based on a [(OC)3Re(l-Br)2Re(CO)3] core. On the other hand, the
[(PhS)(Cl)C@C(H)–N@CPh2] (1b) (Scheme 2) [13e,13f]. An X-ray
diffraction analysis performed on this yellowish crystalline solid
confirmed the conservation of the transoid conformation of the
azabutadiene array found in precursor 1a and the cis-disposition
non-bonding Re ꢀ ꢀ ꢀ Re distance of 3.6958(3) Å is the shortest one re-
ported for this family. In fact, both the folding angle and Re ꢀ ꢀ ꢀ Re dis-
tances depend on the E–E bond length, which is the shortest one
[1.447(6) Å] in azine-bridge of 2a. The structural data show the fol-
lowing evolution of E–E and Re ꢀ ꢀ ꢀ Re separations (Å) and E–E folding
angles (°): S2Ph2 2.140(9), 3.782(2), 33.0 [15a]; P2Ph4 2.308(6),
3.890(1), 23.4 [15e]; Te2Ph2 2.794(5), 3.945(2), 12.1 [15d]; Sb2Ph4
2.826(4), 3.970(2), 10.7[15f]. Note that, apparently, this correlation
2
Selected data for 2b: IR (CH2Cl2): 2044m, 2031s, 1936vs, 1913s cmꢁ1. Anal. Calc.
for C32H20Cl2N2O6Re2 CHCl3: C, 36.32; H, 1.94; N, 2.57. Found: C, 36.40%; H, 1.95%; N,
2.66%.

1062
R. Kinghat et al. / Inorganic Chemistry Communications 11 (2008) 1060–1063
Fig. 2. View of the molecular structure of 1b. The aromatic hydrogen atoms are
omitted for clarity. Selected bond lengths [Å] and angles [°]: N–C(1) 1.297(3), N–
C(2) 1.391(3), C(2)–C(3) 1.335(3), C(3)–Cl 1.747(3), C(3)–S 1.736(3), S-C(16)
1.773(3), C(1)–C(4) 1.479(4), C(1)–C(10) 1.497(3); S–C(3)–Cl 117.0(2), C(2)–C(3)–
S 125.1(2), C(2)–C(3)–Cl 117.8(2), N–C(2)–C(3) 122.9(3), C(1)–N–C(2) 118.6(2), N–
C(1)–C(4) 119.1(3), N–C(1)–C(10) 122.6(2), C(4)–C(1)–C(10) 118.4(2), C(3)–S–C(16)
102.1(1).
of the thioether and the imine group about the vinylic C@C bond
(Fig. 2).3
Ligand 1b is readily coordinated quantitatively within 1 h in a
halide-bridge cleavage reaction on [Re(CO)3(THF)(l-Br)]2 leading
to the S,N-chelate complex fac-[(OC)3ReBr{(PhS)(Cl)C@C(H)–
N@CPh2}] (3), which was isolated in 84% yield in form of a red
air-stable solid.4
Fig. 3. View of the molecular structure of 3. The aromatic hydrogen atoms are
omitted for clarity. Selected bond lengths [Å] and angles [°]: Re–Br 2.6269(5), Re–S
2.464(1), Re–N 2.266(3), Re–C(22) 1.919(4), Re–C(23) 1.900(5), Re–C(24) 1.924(5),
C(3)–S 1.762(4), C(3)–Cl 1.739(4), C(2)–C(3) 1.323(6), N–C(2) 1.411(5), N–C(1)
1.335(5); N–Re–Br 80.83(9), N–Re–S 80.44(9), N–Re–C(22) 170.2(2), N–Re–C(23)
97.7(1), N–Re–C(24) 98.9(1), S–Re–C(24) 172.7(1), S–Re–C(23) 98.4(1), S–Re–C(22)
92.0(1), Br–Re–S 81.07(3), C(22)–Re–Br 91.8(1), C(23)–Re–Br 178.5(1), C(24)–Re–Br
91.6(1), N–C(2)–C(3) 121.7(4), C(1)–N–C(2) 117.4(3), S–C(3)–C(2) 123.8(3).
The fac-arrangement of the three carbonyls and the S,N-chela-
tion of the azabutadiene ligand is also corroborated by an X-ray
diffraction analysis performed on a single crystal of complex 3
(Fig. 3).5 The octahedral coordination sphere around Re consists of
a 5-membered S,N-bound organic chelate ring, a bromo ligand in
cis-position relative to the imine-N atom and the sulphur atom,
and three facially arranged carbonyl ligands. The Re–Br bond length
compares with that of [ReBr(CO)5] [2.6269(5) Å vs. 2.619(2) Å] [20].
The Re–N bond length of 2.266(3) Å lies in the same range as the
mean Re–N value of 2a [2.263(4) Å], the C@N bond distance of the
chelating azabutadiene ligand is markedly longer than that of 1b
[1.335(5) Å vs. 1.299(3) Å]. Probably due to the rigidity of the chelate
ring, the dative Re–S bond of 2.464(1) Å is somewhat shorter than
the averaged Re–S distance of about 2.50 Å encountered in other
Re(I) complexes ligated by PhS–thioether donors [21–23]. Probably
around 360 nm. Upon excitation at 460 nm, two similar broad,
structureless emission maxima at 508 and 535 nm are observed.
The emissions of 2a,b depend slightly on the excitation wavelength
and are comparable to those reported for other dimeric rhenium
complexes of this kind [25]. The absorption spectrum of 3 exhibits
two maxima at 270 and 344 nm. After excitation of 1b and 3 at 360
and 450 nm, the emission maxima were observed at 450 and
617 nm, respectively (Fig. 4). Emissions in a similar spectral range
have been observed in fac-XRe(CO)3(a-diimine) compounds and
were attributed to an emission from a MLCT excited state [6a,5].
In conclusion, it has been demonstrated for the first time that
benzophenone azine may act as bridging ligand. The preparation
for the same reason, some
p-conjugation between one phenyl
of complexes [(OC)3Re(
completes the literature-known series of related di-nuclear com-
plexes [(OC)3Re( -PhnEEPhn)( -Hal)2Re(CO)3] (E = S, Se, Te, P, As,
l-Ph2C@N–N@CPh2)(l-Hal)2Re(CO)3] 2
[C(4) through C(9)] and the azadiene chain C(1)–N–C(2)–C(3) ob-
served in the ligand 1b (dihedral angle = 12.5(2)°) is broken upon
complexation in 3 [dihedral angle = 52.5(3)°]. The dihedral angle be-
tween the SPh-substituent and the azadiene chain remains with
87.4(2)° unchanged in both the structures of 1b and 3. Overall, the
ligand arrangement of 3 is reminiscent to that reported for the
S,N-chelate complex fac-[(OC)3ReBr{bis(methylthio)pyrrolo[1,2-
a]benzimidzol-1-one}] [24].
l
l
Sb). As shown in the case of the S,N-chelate complex 3, ligand 1b
is prone to ligate to metal centers both via the soft thioether
1
The electronic absorption spectra of the di-nuclear complexes
2a and 2b display both one maximum at 267 nm with a shoulder
1b
0.8
3
0.6
3
Crystal data for 1b (293(2) K) C21H16ClNS: Mr = 349.86, orthorhombic, Pcab, a =
9.8697(2) Å, b = 16.1390(4) Å, c = 22.8024(6) Å, V = 3632.1(1) Å3,
l ,
= 0.326 mmꢁ1
Z = 8; d = 1.280 g/cm3, Mo K
a = 0.71073 Å, Nonius Kappa CCD; structure refined by
0.4
0.2
0
full-matrix least-squares on F2 to give final indices R1 = 0.0469 and wR2 = 0.0913;
GOF = 0.866.
4
Selected data for 3: IR (CH2Cl2): 2036 vs., 1945 s, 1907 s cmꢁ1 1H NMR (CDCl3): d
.
7.18–7.94 (m, 16H, phenyl + Hvinyl). Anal. Calc. for C24H16BrNO3ReS: C, 41.18; H, 2.30;
N, 2.00. Found: C, 40.98%; H, 2.16%; N, 2.03%.
5
Crystal data for 3 (at 120(2) K) C24H16BrNO3ReS: Mr = 700.00, monoclinic, P21/n,
410
510
610
710
a = 14.2621(3) Å, b = 9.4314(2) Å, c = 18.3687(3) Å, b = 110.369(2)°, V = 2316.30(8) Å3,
Z = 4, d = 2.007 g/cm3; Nonius Kappa CCD, Mo
K
a
= 0.71073 Å, l ¼ 6:850 mmꢁ1
,
λ [nm]
structure refined by full-matrix least-squares on observed F2 to give final indices
R
1 = 0.0365 and wR2 = 0.0714, GOF = 0.967.
Fig. 4. Normalized emission spectra of 1b and 3 in CH2Cl2 at room temperature.

R. Kinghat et al. / Inorganic Chemistry Communications 11 (2008) 1060–1063
1063
[13] (a) S. Jacquot, A. Belaissaoui, G. Schmitt, B. Laude, M.M. Kubicki, O. Blacque,
Eur. J. Org. Chem. (1999) 1541;
function and the harder imine nitrogen. In order to investigate and
to understand in more detail the photophysical properties of other
S,N-chelate complexes, we are currently preparing a series of
Mn(I), Re(I) and Ru(II) complexes ligated by various functionalized
2-azabutadiene ligands of type [(RS)2C@C(H)–N@CAr2].
(b) S. Jacquot-Rousseau, G. Schmitt, B. Laude, M.M. Kubicki, P. Delarue, Acta
Cryst. E58 (2002) 364;
(c) M. Knorr, G. Schmitt, M.M. Kubicki, E. Vigier, Eur. J. Inorg. Chem. (2003)
514;
(d) S. Jacquot-Rousseau, A. Khatyr, G. Schmitt, M. Knorr, M.M. Kubicki, O.
Blacque, Inorg. Chem. Commun. 8 (2005) 610;
(e) S. Jacquot-Rousseau, G. Schmitt, A. Khatyr, M. Knorr, E. Vigier, M.M.
Kubicki, O. Blacque, Eur. J. Org. Chem. (2006) 1555;
(f) Regioselective formation of the cis-isomer Z-[(PhS)(H)C@C(H)–Fc] is also
observed upon attack of NaSPh on 2,2-dibromo-vinylferrocene-[Br2C@C(H)–
Fc] (see Ref. [23]).
Acknowledgement
Financial support from the Région of Franche-Comté for a Hor-
iba JOBIN-YVON Fluorolog fluorescence spectrometer is gratefully
acknowledged.
[14] (a) D. Vitali, F. Calderazzo, Gazz. Chim. Italy 102 (1972) 587;
(b) W. Hieber, W. Opavsky, W. Rohm, Chem. Ber. 101 (1968) 2244;
(c) F. Calderazzo, I.P. Mavani, D. Vitali, I. Bernal, J.D. Korp, J.L. Atwood, J.
Organomet. Chem. 160 (1978) 207.
[15] (a) F. Calderazzo, I. Bernal, J.L. Atwood, F. Calderazzo, D. Vitali, Gazz. Chim.
Italy 106 (1976) 971;
Appendix A. Supplementary material
CCDC 682377, 682378 and 682379 contain the supplementary
crystallographic data for 1b, 2a and 3. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data_request/cif. Supplementary data
associated with this article can be found, in the online version, at
doi:10.1016/j.inoche.2008.05.022.
(b) F. Calderazzo, I. Bernal, J.L. Atwood, F. Calderazzo, D. Vitali, Israel J. Chem.
15 (1977) 153;
(c) . The following data have been reported for [(OC)3Re(l-PhSeSePh)(l-
Br)2Re(CO)3]: Se–Se 2.41(2) Å, Re Re 3.90(4) Å, folding angle 31°J. Korp, I.
Bernal, J.L. Atwood, F. Calderazzo, D. Vitali, J. Chem. Soc., Dalton Trans. (1979)
1492;
(d) F. Calderazzo, D. Vitali, R. Poli, J.L. Atwood, R.D. Rogers, J.M. Cummings, I.
Bernal, J. Chem. Soc., Dalton Trans. (1981) 1004;
(e) J.L. Atwood, J.K. Newell, W.E. Hunter, I. Bernal, F. Calderazzo, I.P. Mavani, D.
Vitali, J. Chem. Soc., Dalton Trans. (1978) 1189;
(f) I. Bernal, J.D. Korp, F. Calderazzo, R. Poli, D. Vitali, J. Chem. Soc., Dalton
Trans. (1984) 1945.
References
[16] (a) A.K. Saha, M.M. Hosain, D.S. Grubisha, D.W. Bennett, J. Chem. Cryst. 25
(1995) 383;
[1] D.J. Temple, L.K. Johnson, R.L. Huff, P.S. White, M. Brookhart, J. Am. Chem. Soc.
122 (2000) 6861.
(b) D.J. Wolstenholme, T.S. Cameron, J. Phys. Chem. A 110 (2006) 8970.
[17] C.H. Stapfer, R.W. D’Andrea, Inorg. Chem. 10 (1971) 1224.
[18] J. Fornies, B. Menjon, M.M. Cassani, N. Gomez, M. Tomas, Organometallics 11
(1992) 1187.
[19] S. Bordoni, L. Busetto, M.M. Cassani, V.G. Albano, P. Sabatino, Inorg. Chim. Acta
222 (1994) 267.
[20] L.C. Porter, A.H. Reid, J.P. Fackler, Acta Cryst. C48 (1992) 908.
[21] M. Knorr, F. Guyon, I. Jourdain, S. Kneifel, J. Frenzel, C. Strohmann, Inorg. Chim.
Acta 350 (2003) 455.
[22] H.N. Peindy, F. Guyon, I. Jourdain, M. Knorr, D. Schildbach, C. Strohmann,
Organometallics 25 (2006) 1472.
[2] C. Carfagna, G. Gatti, D. Martini, C. Pettinari, Organometallics 20 (2001) 217.
[3] F. Pelascini, F. Peruch, P.J. Lutz, M. Wesolek, J. Kress, Eur. Polym. J. 41 (2005)
1288.
[4] M. Knorr, in: R.H. Crabtree, M.P. Mingos (Eds.), Comprehensive Organometallic
Chemistry III, Elsevier, Amsterdam, Oxford, 2006, pp. 77–126.
[5] L. Sacksteder, A.P. Zipp, E.A. Brown, J. Streich, J.N. Demas, B.A. DeGraff, Inorg.
Chem. 29 (1990) 4335.
[6] (a) K.S. Schanze, D.B. MacQueen, T.A. Perkins, L.A. Cabana, Coord. Chem. Rev.
122 (1993) 63;
(b) R.A. Kirgan, P.B. Sullivan, D.P. Rillema, Top. Curr. Chem. 281 (2007) 45.
[7] (a) A. Juris, S. Campagna, I. Bidd, J.M. Lehn, R. Ziessel, Inorg. Chem. 27 (1988)
4007;
(b) S. Goeb, A. De Nicola, R. Ziessel, C. Sabatini, A. Barbieri, F. Barigelletti, Inorg.
Chem. 45 (2006) 1173.
[8] (a) V.W.-W. Yam, V.C.-Y. Lau, K.-K. Cheung, J. Chem. Soc., Chem. Commun.
(1995) 295;
(b) V.W.-W. Yam, V.C.-Y. Lau, K.-K. Cheung, Organometallics 14 (1995) 2749.
[9] O.S. Wenger, L.M. Henling, M.W. Day, J.R. Winkler, H.B. Gray, Inorg. Chem. 43
(2004) 2043.
[10] K.K.-W. Lo, J.S.-Y. Lau, V.W.-Y. Fong, N. Zhu, Organometallics 23 (2004) 1098.
[11] S. Sato, A. Sekine, Y. Ohashi, Osamu Ishitani, A.M. Blanco-Rodríguez, J. Antonín
Vlek, Taiju Unno, K. Koike, Inorg. Chem. 46 (2007) 3531.
[12] U. Monkowius, Y.N. Svarsov, T. Fischer, M. Zabel, H. Yersin, Inorg. Chem.
Commun. 10 (2007) 1473.
[23] S. Clement, L. Guyard, M. Knorr, F. Villafañe, C. Strohmann, M.M. Kubicki, Eur. J.
Inorg. Chem. (2007) 5052.
[24] (a) G. Wu, D.R. Glass, D. May, W.H. Watson, D. Wiedenfeld, M.G. Richmond, J.
Organomet. Chem. 690 (2005) 4993;
(b) For other examples of S,N-chelated Re(I) complexes see: R. Carballo, J.S.
Casas, E. Garcia-Martinez, G. Pereiras-Gabian, A. Sanchez, J. Sordo, E.M.
Vazquez-Lopez, J.C. Garcia-Monteagudo, U. Abram, J. Organomet. Chem. 656
(2002) 1;
(c) E.W. Abel, D. Elis, K.G. Orrell, J. Chem. Soc., Dalton Trans. (1992) 2243;
(d) S. Alves, A. Paulo, J.D.G. Correia, A. Domingos, I. Santos, J. Chem. Soc.,
Dalton Trans. (2002) 4714.
[25] (a) V.W-W. Yam, V.C-Y. Lau, L.-X. Wu, J. Chem., Dalton Trans (1998) 1461;
(b) S.-S. Sun, A. Lees, Organometallics 20 (2001) 2353.