Luminescent, Redox-Active Dithiolatobis(imine)platinum(II) Divergent Complexes with Exchangeable Imine Ligands: An Experimental/Computational Study Versus Their Diiminedithiolatoplatinum(II) Convergent Congeners

References

• Balzani, V.; Bergamini, G.; Marchioni, F.; Ceroni, P. Ru(II)-bipyridine Complexes in Supramolecular Systems, Devices and Machines. Coord. Chem. Rev. 2006, 250, 1254–1266. DOI: 10.1016/j.ccr.2005.11.013.
   Web of Science ®Google Scholar
• Schelter, E. J.; Karadas, F.; Avendano, C.; Prosvirin, A. V.; Wernsdorfer, W.; Dunbar, K. R. A Family of Mixed-Metal Cyanide Cubes with Alternating Octahedral and Tetrahedral Corners Exhibiting A Variety of Magnetic Behaviors Including Single Molecule Magnetism. J. Am. Chem. Soc. 2007, 129(26), 8139–8149. DOI: 10.1021/ja0683281.
   PubMed Web of Science ®Google Scholar
• Klosterman, J. K.; Iwamura, M.; Tahara, T.; Fujita, M. Energy Transfer in a Mechanically Trapped Exciplex. J. Am. Chem. Soc. 2009, 131(27), 9478–9479. DOI: 10.1021/ja901674g.
   PubMed Web of Science ®Google Scholar
• Sautter, A.; Kaletaş, B. K.; Schmid, D. G.; Dobrawa, R.; Zimine, M.; Jung, G.; van Stokkum, I. H. M.; De Cola, L.; Williams, R. M.; Würthner, F. Ultrafast Energy-Electron Transfer Cascade in a Multichromophoric Light-Harvesting Molecular Square. J. Am. Chem. Soc. 2005, 127(18), 6719–6729. DOI: 10.1021/ja0448216.
   PubMed Web of Science ®Google Scholar
• Corma, A.; García, H.; Llabrés I Xamena, F. X. Engineering Metal Organic Frameworks for Heterogeneous Catalysis. Chem. Rev. 2010, 110(8), 4606–4655. DOI: 10.1021/cr9003924.
   PubMed Web of Science ®Google Scholar
• Cook, T. R.; Zheng, Y.-R.; Stang, P. J. Metal–Organic Frameworks and Self-Assembled Supramolecular Coordination Complexes: Comparing and Contrasting the Design, Synthesis, and Functionality of Metal–Organic Materials. Chem. Rev. 2013, 113(1), 734–777. DOI: 10.1021/cr3002824.
   PubMed Web of Science ®Google Scholar
• Guo, Z.; Kobayashi, T.; Wang, -L.-L.; Goh, T. W.; Xiao, C.; Caporini, M. A.; Rosay, M.; Johnson, D. D.; Pruski, M.; Huang, W. Selective Host–Guest Interaction between Metal Ions and Metal–Organic Frameworks Using Dynamic Nuclear Polarization Enhanced Solid-State NMR Spectroscopy. Chem. - Eur. J. 2014, 20(49), 16308–16313. DOI: 10.1002/chem.v20.49.
   PubMed Web of Science ®Google Scholar
• Cui, J.; Xu, Z. An Electroactive Porous Network from Covalent Metal–Dithiolene Links. Chem. Commun. 2014, 50(30), 3986–3988. DOI: 10.1039/C4CC00408F.
   PubMed Web of Science ®Google Scholar
• Ghosh, S.; Mukherjee, P. S. Self-Assembly of a Nanoscopic Prism via a New Organometallic Pt3 Acceptor and Its Fluorescent Detection of Nitroaromatics. Organometallics. 2008, 27(3), 316–319. DOI: 10.1021/om701082y.
   Web of Science ®Google Scholar
• Flynn, D. C.; Ramakrishna, G.; Yang, H.-B.; Northrop, B. H.; Stang, P. J.; Goodson, T. Ultrafast Optical Excitations in Supramolecular Metallacycles with Charge Transfer Properties. J. Am. Chem. Soc. 2010, 132(4), 1348–1358. DOI: 10.1021/ja9082655.
   PubMed Web of Science ®Google Scholar
• Mauro, M.; Aliprandi, A.; Cebrián, C.; Wang, D.; Kübel, C.; De Cola, L. Self-Assembly of a Neutral Platinum(Ii) Complex into Highly Emitting Microcrystalline Fibers through Metallophilic Interactions. Chem. Commun. 2014, 50(55), 7269–7272. DOI: 10.1039/C4CC01045K.
   PubMed Web of Science ®Google Scholar
• Eisenberg, R.; Gray, H. B. Noninnocence in Metal Complexes: A Dithiolene Dawn. Inorg. Chem. 2011, 50(20), 9741–9751. DOI: 10.1021/ic2011748.
   PubMed Web of Science ®Google Scholar
• Espa, D.; Pilia, L.; Makedonas, C.; Marchiò, L.; Mercuri, M. L.; Serpe, A.; Barsella, A.; Fort, A.; Mitsopoulou, C. A.; Deplano, P. Role of the Acceptor in Tuning the Properties of Metal [M(II) = Ni, Pd, Pt] Dithiolato/Dithione (Donor/Acceptor) Second-Order Nonlinear Chromophores: Combined Experimental and Theoretical Studies. Inorg. Chem. 2014, 53(2), 1170–1183. DOI: 10.1021/ic402738b.
   PubMed Web of Science ®Google Scholar
• Smucker, B. W.; Hudson, J. M.; Omary, M. A.; Dunbar, K. R. Structural, Magnetic, and Optoelectronic Properties of Diiminedithiolatoplatinum(II) and -Palladium(II) Complexes and Their Charge-Transfer Adducts with Nitrile Acceptors. Inorg. Chem. 2003, 42(15), 4714–4723. DOI: 10.1021/ic0259585.
   PubMed Web of Science ®Google Scholar
• Islam, A.; Sugihara, H.; Hara, K.; Singh, L. P.; Katoh, R.; Yanagida, M.; Takahashi, Y.; Murata, S.; Arakawa, H.; Fujihashi, G. Dye Sensitization of Nanocrystalline Titanium Dioxide with Square Planar Platinum(II) Diimine Dithiolate Complexes. Inorg. Chem. 2001, 40(21), 5371–5380.
   PubMed Web of Science ®Google Scholar
• Browning, C.; Hudson, J. M.; Reinheimer, E. W.; Kuo, F.-L.; McDougald, R. N.; Rabaâ, H.; Pan, H.; Bacsa, J.; Wang, X.; Dunbar, K. R.; et al. Synthesis, Spectroscopic Properties, and Photoconductivity of Black Absorbers Consisting of Pt(Bipyridine)(Dithiolate) Charge Transfer Complexes in the Presence and Absence of Nitrofluorenone Acceptors. J. Am. Chem. Soc. 2014, 136(46), 16185–16200. DOI: 10.1021/ja506583k.
   PubMed Web of Science ®Google Scholar
• Pintus, A.; Aragoni, M. C.; Bellec, N.; Devillanova, F. A.; Lorcy, D.; Isaia, F.; Lippolis, V.; Randall, R. A. M.; Roisnel, T.; Slawin, A. M. Z.; et al. Structure–Property Relationships in PtII Diimine-Dithiolate Nonlinear Optical Chromophores Based on Arylethylene-1,2-Dithiolate and 2-Thioxothiazoline-4,5-Dithiolate. Eur. J. Inorg. Chem. 2012, 2012(22), 3577–3594. DOI: 10.1002/ejic.201200346.
   Google Scholar
• Zhang, J.; Du, P.; Schneider, J.; Jarosz, P.; Eisenberg, R. Photogeneration of Hydrogen from Water Using an Integrated System Based on TiO2 and Platinum(II) Diimine Dithiolate Sensitizers. J. Am. Chem. Soc. 2007, 129(25), 7726–7727. DOI: 10.1021/ja071789h.
   PubMed Web of Science ®Google Scholar
• Zheng, B.; Sabatini, R. P.; Fu, W.-F.; Eum, M.-S.; Brennessel, W. W.; Wang, L.; McCamant, D. W.; Eisenberg, R. Light-Driven Generation of Hydrogen: New Chromophore Dyads for Increased Activity Based on Bodipy Dye and Pt(Diimine)(Dithiolate) Complexes. Proc. Natl. Acad. Sci. 2015, 112(30), E3987–E3996. DOI: 10.1073/pnas.1509310112.
   PubMed Web of Science ®Google Scholar
• Cummings, S. D.; Eisenberg, R. Tuning the Excited-State Properties of Platinum(II) Diimine Dithiolate Complexes. J. Am. Chem. Soc. 1996, 118(8), 1949–1960. DOI: 10.1021/ja951345y.
   Web of Science ®Google Scholar
• Moorcraft, L. P.; Jack, L. A.; Jennings, J. R.; Peter, L. M.; Yellowlees, L. J.; Robertson, N. Synthesis and Properties of [Pt(4-Co2ch3-Py)2(Dmit)] and [Pt(4-No2-Py)2(Mnt)]: Exploring Tunable Pt Dyes. Polyhedron. 2009, 28(18), 4084–4090. DOI: 10.1016/j.poly.2009.09.017.
   Web of Science ®Google Scholar
• Moorcraft, L. P.; Morandeira, A.; Durrant, J. R.; Jennings, J. R.; Peter, L. M.; Parsons, S.; Turner, A.; Yellowlees, L. J.; Robertson, N. Synthesis and Properties of [Pt(4-Co2ch3-Py)2(Mnt)]: Comparison of Pyridyl and Bipyridyl-Based Dyes for Solar Cells. Dalton Trans. 2008, (48), 6940–6947. DOI: 10.1039/b811943k.
   PubMed Web of Science ®Google Scholar
• Derry, P. J.; Wang, X.; Smucker, B. W. Tetra-pyrazine-platinum(II) bis-(tetra-fluoro-borate) acetonitrile hemisolvate . Acta Crystallogr. Sect. E Struct. Rep. Online 2008, 64(Pt 11), m1449. DOI: 10.1107/S1600536808033679.
   PubMedGoogle Scholar
• Wendt, F. O.; Kaiser, N.-F. K.; Elding, L. I. Acetonitrile and Propionitrile Exchange at palladium(II) and platinum(II) †. J. Chem. Soc. Dalton Trans. 1997, (24), 4733–4738. DOI: 10.1039/a705048h.
   Google Scholar
• Davison, A.; Holm, R. H.; Benson, R. E.; Mahler, W. Metal Complexes Derived from Cis-1,2-Dicyano-1,2-Ethylenedithiolate and Bis(Trifluoromethyl)-1,2-dithiete. ‎Inorg. Synth. 1967, 10, 8–26. Muetterties, E. L., Mc-GrawHill Inc.
   Google Scholar
• Bruker. Saint; Bruker AXS Inc: Madison, Wisconsin, USA, 2007.
   Google Scholar
• Bruker. SADABS; Bruker AXS Inc: Madison, Wisconsin, USA, 2007.
   Google Scholar
• Bruker. XPREP; Bruker AXS Inc: Madison, Wisconsin, USA, 2007.
   Google Scholar
• Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. The Anatomy of a Comprehensive Constrained, Restrained Refinement Program for the Modern Computing Environment - Olex2 Dissected. Acta Crystallogr. Sect. A Found. Crystallogr. 2015, 71(1), 59–75. DOI: 10.1107/S2053273314022207.
   Google Scholar
• Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crsytallogr. 2009, 42(2), 339–341. DOI: 10.1107/S0021889808042726.
   Web of Science ®Google Scholar
• Frisch, M. J.; W. T, G.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; et al. 09 Revision E01, Wallingford, CT, USA, 2016.
   Google Scholar
• Becke, A. D.;. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Phys. Rev. A. 1988, 38(6), 3098–3100. DOI: 10.1103/PhysRevA.38.3098.
   PubMed Web of Science ®Google Scholar
• Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Results Obtained with the Correlation Energy Density Functionals of Becke and Lee, Yang and Parr. Chem. Phys. Lett. 1989, 157(3), 200–206. DOI: 10.1016/0009-2614(89)87234-3.
   Web of Science ®Google Scholar
• Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theor. Chem. Acc. 2008, 120(1), 215–241.
   Web of Science ®Google Scholar
• Cundari, T. R.; Stevens, W. J. Effective Core Potential Methods for the Lanthanides. J. Chem. Phys. 1993, 98(7), 5555–5565. DOI: 10.1063/1.464902.
   Web of Science ®Google Scholar
• Stevens, W. J.; Basch, H.; Krauss, M. Compact Effective Potentials and Efficient Shared‐Exponent Basis Sets for the First‐ and Second‐Row Atoms. J. Chem. Phys. 1984, 81(12), 6026–6033. DOI: 10.1063/1.447604.
   Web of Science ®Google Scholar
• Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Relativistic Compact Effective Potentials and Efficient, Shared-Exponent Basis Sets for the Third-, Fourth-, and Fifth-Row Atoms. Can. J. Chem. 1992, 70(2), 612–630. DOI: 10.1139/v92-085.
   Web of Science ®Google Scholar
• Zheng, Y.-R.; Stang, P. J. Direct and Quantitative Characterization of Dynamic Ligand Exchange between Coordination-Driven Self-Assembled Supramolecular Polygons. J. Am. Chem. Soc. 2009, 131(10), 3487–3489. DOI: 10.1021/ja809788x.
   PubMed Web of Science ®Google Scholar
• Willermann, M.; Mulcahy, C.; Sigel, R. K. O.; Cerdà, M. M.; Freisinger, E.; Sanz Miguel, P. J.; Roitzsch, M.; Lippert, B. Pyrazine as a Building Block for Molecular Architectures with PtII. Inorg. Chem. 2006, 45(5), 2093–2099. DOI: 10.1021/ic051966k.
   PubMed Web of Science ®Google Scholar
• Melnik, M.; Holloway, C. E. Stereochemistry of Platinum Coordination Compounds. Coord. Chem. Rev. 2006, 250(17), 2261–2270. DOI: 10.1016/j.ccr.2006.02.020.
   Web of Science ®Google Scholar
• Adams, C. J.; Fey, N.; Parfitt, M.; Pope, S. J. A.; Weinstein, J. A. Synthesis, Structures and Properties of a New Series of Platinum–Diimine–Dithiolate Complexes. Dalton Trans. 2007, (39), 4446–4456. DOI: 10.1039/b709252k.
   PubMed Web of Science ®Google Scholar
• Makedonas, C.; Mitsopoulou, C. A.; Lahoz, F. J.; Balana, A. I. Synthesis, Characterization, and Crystal Structure of the Pd(Phen)(Bdt) Complex. A DFT and TDDFT Study of Its Ground Electronic and Excited States Compared to Those of Analogous Complexes. Inorg. Chem. 2003, 42(26), 8853–8865. DOI: 10.1021/ic034978j.
   PubMed Web of Science ®Google Scholar
• Connick, W. B.; Gray, H. B. Photooxidation of Platinum(II) Diimine Dithiolates. J. Am. Chem. Soc. 1997, 119(48), 11620–11627. DOI: 10.1021/ja9723803.
   Web of Science ®Google Scholar
• Bevilacqua, J. M.; Eisenberg, R. Synthesis and Characterization of Luminescent Square-Planar Platinum(II) Complexes Containing Dithiolate or Dithiocarbamate Ligands. Inorg. Chem. 1994, 33(13), 2913–2923. DOI: 10.1021/ic00091a034.
   Web of Science ®Google Scholar
• Wei, C. H.; Hingerty, B. E.; Busing, W. R. Structure of tetrakis(pyridine)platinum(II) Chloride Trihydrate: Unconstrained Anisotropic Least-Squares Refinement of Hydrogen and Non-Hydrogen Atoms from Combined X-Ray-Neutron Diffraction Data. Acta Crystallogr., Sect. C: Struct. Chem. 1989, 45(1), 26–30. DOI: 10.1107/S0108270188009515.
   Google Scholar
• Geary, E. A. M.; Yellowlees, L. J.; Jack, L. A.; Oswald, I. D. H.; Parsons, S.; Hirata, N.; Durrant, J. R.; Robertson, N. Synthesis, Structure, and Properties of [Pt(Ii)(Diimine)(Dithiolate)] Dyes with 3,3‘-, 4,4‘-, and 5,5‘-Disubstituted Bipyridyl: Applications in Dye-Sensitized Solar Cells. Inorg. Chem. 2005, 44(2), 242–250. DOI: 10.1021/ic048799t.
   PubMed Web of Science ®Google Scholar
• Nesterov, V. N.; Reinheimer, E. W.; Smucker, B. W. (2,2`-Bipyridine)(1,2-Dicyanoethene-1,2-Dithiolato)Platinum(Ii). IUCrData. 2019, 4(x190158). DOI: 10.1107/S2414314619001585.
   Google Scholar
• Lazarides, T.; McCormick, T. M.; Wilson, K. C.; Lee, S.; McCamant, D. W.; Eisenberg, R. Sensitizing the Sensitizer: The Synthesis and Photophysical Study of Bodipy−Pt(II)(diimine)(dithiolate) Conjugates. J. Am. Chem. Soc. 2011, 133(2), 350–364. DOI: 10.1021/ja1070366.
   PubMed Web of Science ®Google Scholar
• Zuleta, J. A.; Bevilacqua, J. M.; Proserpio, D. M.; Harvey, P. D.; Eisenberg, R. Spectroscopic and Theoretical Studies on the Excited State in Diimine Dithiolate Complexes of platinum(II). Inorg. Chem. 1992, 31(12), 2396–2404. DOI: 10.1021/ic00038a019.
   Web of Science ®Google Scholar
• Zuleta, J. A.; Burberry, M. S.; Eisenberg, R. Platinum(II) Diimine Dithiolates. New Solution Luminescent Complexes. Coord. Chem. Rev. 1990, 97(47). DOI: 10.1016/0010-8545(90)80079-9.
   Google Scholar
• Koopmans, T.;. Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica. 1934, 1(1), 104–113. DOI: 10.1016/S0031-8914(34)90011-2.
   Google Scholar
• Guasch, J.; Grisanti, L.; Souto, M.; Lloveras, V.; Vidal-Gancedo, J.; Ratera, I.; Painelli, A.; Rovira, C.; Veciana, J. Intra- and Intermolecular Charge Transfer in Aggregates of Tetrathiafulvalene-Triphenylmethyl Radical Derivatives in Solution. J. Am. Chem. Soc. 2013, 135(18), 6958–6967. DOI: 10.1021/ja400281b.
   PubMed Web of Science ®Google Scholar
• Pap, J. S.; Benedito, F. L.; Bothe, E.; Bill, E.; DeBeer George, S.; Weyhermüller, T.; Wieghardt, K. Dimerization Processes of Square Planar [Ptii(Tbpy)(Dithiolato•)]+ Radicals. Inorg. Chem. 2007, 46(10), 4187–4196. DOI: 10.1021/ic070130+.
   PubMed Web of Science ®Google Scholar
• Spanggaard, H.; Prehn, J.; Nielsen, M. B.; Levillain, E.; Allain, M.; Becher, J. Multiple-Bridged Bis-Tetrathiafulvalenes: New Synthetic Protocols and Spectroelectrochemical Investigations. J. Am. Chem. Soc. 2000, 122(39), 9486–9494. DOI: 10.1021/ja000537c.
   Web of Science ®Google Scholar
• Spruell, J. M.; Coskun, A.; Friedman, D. C.; Forgan, R. S.; Sarjeant, A. A.; Trabolsi, A.; Fahrenbach, A. C.; Barin, G.; Paxton, W. F.; Dey, S. K.; et al. Highly Stable Tetrathiafulvalene Radical Dimers in [3]Catenanes. Nat. Chem. 2010, 2(10). DOI: 10.1038/nchem.749.
   PubMed Web of Science ®Google Scholar
• Zanello, P.;. Inorganic Electrochemistry, The Royal Society of Chemistry: Cambridge, UK, 2003. DOI: 0.1039/9781847551146.
   Google Scholar
• Schindler, J. W.; Adamson, A. W. Emission Quenching and Photochemistry of Aqueous Tetracyanoplatinate(2-). Inorg. Chem. 1982, 21(12), 4236–4240. DOI: 10.1021/ic00142a025.
   Web of Science ®Google Scholar