Organometallics
Article
+
of Pd(0) and Pt(0) Metallocryptands Encapsulating Tl Ion. J. Am.
Chem. Soc. 2000, 122, 10056−10062. (c) Catalano, V. J.; Bennett, B.
L.; Muratidis, S.; Noll, B. C. Unsupported Pt(0)−Tl(I) Bonds in the
Simple [Pt(PPh2Py)3Tl]+Complexes. J. Am. Chem. Soc. 2001, 123,
(18) (a) Reinartz, S.; White, P. S.; Brookhart, M.; Templeton, J. L.
Syntheses of Platinum(IV) Aryl Dihydride Complexes via Arene C−
H Bond Activation. Organometallics 2001, 20, 1709−1712. (b) Zhang,
F.; Kirby, C. W.; Hairsine, D. W.; Jennings, M. C.; Puddephatt, R. J.
Activation of C−H Bonds of Arenes: Selectivity and Reactivity in
Bis(pyridyl) Platinum(II) Complexes. J. Am. Chem. Soc. 2005, 127,
14196−14197. (c) Heyduk, A. F.; Driver, T. G.; Labinger, J. A.;
Bercaw, J. E. Kinetic and Thermodynamic Preferences in Aryl vs
Benzylic C−H Bond Activation with Cationic Pt(II) Complexes. J.
Am. Chem. Soc. 2004, 126, 15034−15035.
1
73. (d) Catalano, V. J.; Malwitz, M. A. Mixed-Metal Metal-
locryptands. Short Metal−Metal Separations Strengthened by a
Dipolar Interaction. J. Am. Chem. Soc. 2004, 126, 6560.
(
10) (a) Alonso, E.; Fornies, J.; Fortuno, C.; Lledos, A.; Martín, A.;
̃
́ ́
Nova, A. Behavior of P−Pt and P−Pd Bonds in Phosphido
Complexes toward Electrophilic Fragments§. Inorg. Chem. 2009, 48,
7
679−7690. (b) Fornies
́
, J.; Fortun
̃
o, C.; Iban
́
̃
ez, S.; Martín, A.;
Mastrorilli, P.; Gallo, V. Behavior of Neutral Phosphido Derivatives of
Platinum and Palladium toward Silver Centers. Inorg. Chem. 2011, 50,
(19) Fornies, J.; Gimenez, N.; Ibanez, S.; Lalinde, E.; Martín, A.;
́ ́ ́
̃
Moreno, M. T. An Extended Chain and Trinuclear Complexes Based
on Pt(II)-M (M = Tl(I), Pb(II)) Bonds: Contrasting Photophysical
Behavior. Inorg. Chem. 2015, 54, 4351−4363.
1
(
0798−10809.
11) (a) Arias, A.; Fornies
́
, J.; Fortun
̃
o, C.; Martín, A.; Mastrorilli, P.;
Gallo, V.; Latronico, M.; Todisco, S. Donor Behaviour of Anionic and
Asymmetric Phosphanido Derivatives of Platinum and Palladium. Eur.
́
J. Inorg. Chem. 2014, 1679−1693. (b) Latronico, M.; Sanchez, S.;
Rizzuti, A.; Gallo, V.; Polini, F.; Lalinde, E.; Mastrorilli, P. Reactivity
(20) Fuertes, S.; Chueca, A. J.; Martín, A.; Sicilia, V. Pt2Tl Building
Blocks for Two-Dimensional Extended Solids: Synthesis, Crystal
Structures, and Luminescence. Cryst. Growth Des. 2017, 17, 4336−
4346.
́
(21) Belío, U.; Fuertes, S.; Martín, A. Synthesis and Characterization
of the phosphinito bridged Pt(i) complex [(PHCy2)Pt(μ-PCy2)-
of a “Pt3Tl” Cluster Containing an Unprecedented Trigonal
Environment for Thallium(I). Inorg. Chem. 2013, 52, 5627−5629.
(22) (a) Rubinstein, L. I.; Pignolet, L. H. Kinetic Investigation of
Homogeneous H -D Equilibration Catalyzed by Pt-Au Cluster
{
κ2P,O-μ-P(O)Cy2}Pt(PHCy2)](Pt-Pt) towards Au(i) and Ag(i)
electrophiles. Dalton Trans. 2013, 42, 2502−2511.
12) Julia, F.; Jones, P. G.; Gonzalez-Herrero, P. Synthesis and
(
́
́
2
2
Photophysical Properties of Cyclometalated Platinum(II) 1,2-
Benzenedithiolate Complexes and Heterometallic Derivatives Ob-
tained from the Addition of [Au(PCy3)]+ Units. Inorg. Chem. 2012,
Compounds. Characterization of the Cluster [(H)Pt(AuPPh ) ]-
3 9
(NO ) . Inorg. Chem. 1996, 35, 6755−6762. (b) Hayoun, R.; Zhong,
3
2
D. K.; Rheingold, A. L.; Doerrer, L. H. Gold(III) and Platinum(II)
Polypyridyl Double Salts and a General Metathesis Route to
Metallophilic Interactions. Inorg. Chem. 2006, 45, 6120−6122.
(c) Zhang, L.-Y.; Xu, L.-J.; Wang, J.-Y.; Zeng, X.-C.; Chen, Z.-N.
Photoluminescence and Electroluminescence of Cationic PtAu2
Heterotrinuclear Complexes with Aromatic Acetylides Metathesis
Route to Metallophilic Interactions. Dalton Trans. 2017, 46, 865−
5
(
1, 5037−5049.
13) (a) Jamali, S.; Ghazfar, R.; Lalinde, E.; Jamshidi, Z.; Samouei,
H.; Shahsavari, H. R.; Moreno, M. T.; Escudero-Adan, E.; Benet-
́
Buchholz, J.; Milic, D. Cyclometalated Heteronuclear Pt/Ag and Pt/
Tl Complexes: a Structural and Photophysical Study. Dalton Trans.
2
014, 43, 1105−1116. (b) Jamali, S.; Mazloomi, Z.; Nabavizadeh, S.
M.; Milic, D.; Kia, R.; Rashidi, M. Cyclometalated Cluster Complex
with a Butterfly-Shaped Pt Ag Core. Inorg. Chem. 2010, 49, 2721−
́
874. (d) Julia, F.; Jones, P. G.; Gonzalez-Herrero, P. Synthesis and
́ ́
Photophysical Properties of Cyclometalated Platinum(II) 1,2-
2
2
2
726.
14) Yersin, H. Highly Efficient OLEDs with Phosphorescent Materials;
Wiley-VCH: New York, 2007.
15) (a) Chassot, L.; von Zelewsky, A. Cyclometalated Complexes
Benzenedithiolate Complexes and Heterometallic Derivatives Ob-
+
(
tained from the Addition of [Au(PCy )] Units. Inorg. Chem. 2012,
3
51, 5037−5049. (e) Stork, J. R.; Rios, D.; Pham, D.; Bicocca, V.;
Olmstead, M. M.; Balch, A. L. Metal−Metal Interactions in
Platinum(II)/Gold(I) or Platinum(II)/Silver(I) Salts Containing
Planar Cations and Linear Anions. Inorg. Chem. 2005, 44, 3466−
3472. (f) Goto, E.; Begum, R. A.; Ueno, C.; Hosokawa, A.;
Yamamoto, C.; Nakamae, K.; Kure, B.; Nakajima, T.; Kajiwara, T.;
Tanase, T. Electron-Deficient Pt M Pt Hexanuclear Metal Strings
(
of Platinum(II): Homoleptic Compounds with Aromatic C,N
Ligands. Inorg. Chem. 1987, 26, 2814−2818. (b) Chassot, L.;
Muller, E.; von Zelewsky, A. cis -Bis( 2-pbenylpyridine)platinum(
11) (CBPPP): A Simple Molecular Platinum Compound. Inorg.
Chem. 1984, 23, 4249−4253. (c) Jolliet, P.; Gianini, M.; von
Zelewsky, A.; Bernardinelli, G.; Stoeckli-Evans, H. Cyclometalated
Complexes of Palladium(II) and Platinum(II): cis-Configured
2
2
2
(M = Pt, Pd) Supported by Triphosphine Ligands. Organometallics
2014, 33, 1893−1904. (g) Yip, H.-K.; Lin, H.-M.; Wang, Y.; Che, C.-
M. Luminescent heterobimetallic complexes. Electronic structure and
spectroscopy of [MPt(dppm)2(C=CPh)2]PF6(M = Au or Ag) and
crystal structure of [AuPt(dppm)2(C=CPh)2]PF6(dppm =
Ph2PCH2PPh2). J. Chem. Soc., Dalton Trans. 1993, 2939−2944.
(23) Bauer, J.; Braunschweig, H.; Damme, A.; Radacki, K. Reversible
Insertion of Platinum into Coinage Group Metal-Halogen Bonds.
Angew. Chem., Int. Ed. 2012, 51, 10030−10033.
(24) (a) Maestri, M.; Sandrini, D.; Balzani, V.; von Zelewsky, A.;
Deuschel-Cornioley, C.; Jolliet, P. Absorption Spectra and Lumines-
cence Properties of Isomeric Platinum (II) and Palladium (II)
Complexes containing 1,1?-biphenyldiyl, 2-phenylpyridine, and 2,2?-
bijpyridine as ligands. Helv. Chim. Acta 1988, 71, 1053−1059.
(25) Deuschel-Cornioley, C.; Luond, R.; von Zelewsky, A.
̈
̈
Cyclometalated Compounds of Platinum(II) with two different C,
N-aromatic ligands. Helv. Chim. Acta 1989, 72, 377−382.
(26) (a) Ai, Y.; Li, Y.; Ma, H.; Su, C.-Y.; Yam, V. W.-W.
Cyclometalated Platinum(II) Complexes of 1,3-Bis(1-n-butylpyrazol-
3-yl)benzenes: Synthesis, Characterization, Electrochemical, Photo-
physical, and Gelation Behavior Studies. Inorg. Chem. 2016, 55,
11920−11929. (b) Chen, Y.; Lu, W.; Che, C.-M. Luminescent Pincer-
Type Cyclometalated Platinum(II) Complexes with Auxiliary
Isocyanide Ligands: Phase-Transfer Preparation, Solvatomorphism,
and Self-Aggregation. Organometallics 2013, 32, 350−353. (c) Turner,
E.; Bakken, N.; Li, J. Cyclometalated platinum complexes with
̑
Homoleptic and Heteroleptic Compounds with Aromatic CN
Ligands. Inorg. Chem. 1996, 35, 4883−4888. (d) Gianini, M.;
Forster, A.; Haag, P.; von Zelewsky, A.; Stoeckli-Evans, H. Square
Planar (SP-4) and Octahedral (OC-6) Complexes of Platinum(II)
and -(IV) with Predetermined Chirality at the Metal Center. Inorg.
Chem. 1996, 35, 4889−4895. (e) Gianini, M.; von Zelewsky, A.;
Stoeckli-Evans, H. Chiral Cyclometalated Platinum(II) and
Palladium(II) Complexes with Derivatives of Thienylpyridine as
Ligands: Helical Distortion of the Square Planar (SP-4) Geometry.
Inorg. Chem. 1997, 36, 6094−6098.
(16) (a) Abramovitch, R. A.; Saha, J. G. 404. Aromatic substitution.
Part III. Reaction of pyridine with ortho-substituted phenyl radicals,
and the influence of oxygen upon isomer ratios in the Gomberg-Hey
reaction. J. Chem. Soc. 1964, 2175−2187. (b) Kalyani, D.; Dick, A. R.;
Anani, W. Q.; Sanford, M. S. Scope and selectivity in palladium-
catalyzed directed C-H bond halogenation reactions. Tetrahedron
2
006, 62, 11483−11498. (c) Kim, K.; Jung, Y.; Lee, S.; Kim, M.; Shin,
D.; Byun, H.; Cho, S. J.; Song, H.; Kim, H. Directed C−H Activation
and Tandem Cross-Coupling Reactions Using Palladium Nano-
catalysts with Controlled Oxidation. Angew. Chem., Int. Ed. 2017, 56,
6
(
952−6956.
17) Julia, F.; Gonzalez-Herrero, P. Aromatic C-H Activation in the
́
́
Triplet Excited State of Cyclometalated Platinum(II) Complexes
Using Visible Light. J. Am. Chem. Soc. 2016, 138, 5276−5282.
K
Organometallics XXXX, XXX, XXX−XXX