This paper is an overview concerning the preparations and properties as well as possible applications of neutral (one component) metal 1,2-dithiolenes (and selenium analogues). The structural, chemical, electrochemical, optical and electrical behavior of these complexes depend strongly on the nature of ligand and/or the metal. The results of unsymmetrical in comparison to those of symmetrical complexes related to the properties of materials in the solid state are primarily discussed. The optical absorption spectra exhibit strong bands in the near IR spectral region ca. 700 to ca. 1950 nm. X-ray crystal structure solutions show that the complexes usually have square-planar geometry with S–S and/or M–S contacts. Some of them behave as semiconductors or conductors (metals) and are stable in air. The cyclic voltammograms at negative potentials are different from the corresponding potentials of tetrathiafulvalenes (TTFs). As a consequence, the LUMO bands occur at much lower levels than those of TTFs. Consequently, electrical measurements under conditions of field effect transistors exhibit n-type or ambipolar behavior. Illumination of materials with high power lasers exhibits non-linear optical behavior. These properties enable metal 1,2-dithiolene complexes to be classified as promising candidates for optical and electronic applications, (e.g., saturable absorbers, ambipolar inverters).
References
[1]
Schrauzer, G.N.; Mayweg, V.P. Reaction of diphenylacetylene with nickel sulfides. J. Am. Chem. Soc. 1962, 84, 3221, doi:10.1021/ja00875a061.
[2]
Schrauzer, G.N.; Mayweg, V.P. Preparation, reactions, and structure of bisdithio-α-diketone complexes of nickel, palladium, and platinum. J. Am. Chem. Soc. 1965, 87, 1483–1489, doi:10.1021/ja01085a014.
[3]
Sartain, D.; Truter, M.R. Crystal structure of bis(dithiobenzil)nickel. J. Chem. Soc. 1967, doi:10.1039/j19670001264.
[4]
McCleverty, J.A. Metal 1,2-dithiolenes and related compounds. Prog. Inorg. Chem. 1968, 10, 49–156, doi:10.1002/9780470166116.ch2.
[5]
Underhill, A.E.; Ahmad, M.M. A new one-dimensional metal with conduction through bis(dicyanoethylenedithiolato)platinum anions. J. Chem. Soc. Chem. Commun. 1981, doi:10.1039/c39810000067.
[6]
Papavassiliou, G.C. Some new conducting solids: Cation-deficient metal dimercaptodithiolenes and selenium analogs. Z. Naturforsch. 1982, 37b, 825–827.
[7]
Alvarez, S.; Vicente, R.; Hoffmann, R. Dimerization and stacking in transition-metal bisdithiolenes and tetrathiolates. J. Am. Chem. Soc. 1985, 107, 6253–6277, doi:10.1021/ja00308a018.
[8]
Clemenson, P.I. The chemistry and solid-state properties of nickel, palladium and platinum bis(maleonitriledithiolate) compounds. Coord. Chem. Rev. 1990, 106, 171–203, doi:10.1016/0010-8545(60)80003-3.
[9]
Papavassiliou, G.C.; Kakoussis, V.G.; Lagouvardos, D.J.; Mousdis, G.A. Transition-metal 1,2-diheterolenes and polyheterotetraheterafulvalenes: Precursors of conducting solids. Mol. Cryst. Liqid Cryst. 1990, 181, 171–184.
[10]
Muellerwesterhoff, U.T.; Vance, B.; Yoon, D.I. The synthesis of dithiolene dyes with strong near-IR absorption. Tetrahedron 1991, 47, 909–932, doi:10.1016/S0040-4020(01)80932-7.
[11]
Olk, R.M.; Olk, B.; Dietzsch, W.; Kirmse, R.; Hoyer, E. The chemistry of 1,3-dithiole-2-thione-4,5-dithiolate (dmit). Coord. Chem. Rev. 1992, 117, 99–131, doi:10.1016/0010-8545(92)80021-I.
[12]
Papavassiliou, G.C.; Terzis, A.; Delhaes, P. Tetrachalcogenafulvalenes, metal 1,2-dichalcogenolenes and their conducting salts. In Handbook of Ogranic Conductive Molecules and Polymers; Nalwa, H.S., Ed.; John Wiley & Sons: Hoboken, NJ, USA, 1997; Volume 1, pp. 152–214.
[13]
Kotov, A.I.; Buravov, L.I.; Yagubskii, E.B.; Khasanov, S.S.; Zorina, L.V.; Shibaeva, R.P.; Canadell, E. Comparative study of BEDT TTF and Ni(dddt)2 electroconducting salts with the HXO4 (X = Se, S) anions. Synth. Met. 2001, 124, 357–362, doi:10.1016/S0379-6779(01)00374-5.
[14]
Watanabe, E.; Fujiwara, M.; Yamaura, J.; Kato, R. Synthesis and properties of novel donor-type metal-dithiolene complexes based on 5,6-dihydro-1,4-dioxine-2,3-dithiol (edo). J. Mater. Chem. 2001, 11, 2131–2141, doi:10.1039/b102000p.
[15]
Robertson, N.; Cronin, L. Metal bis-1,2-dithiolene complexes in conducting or magnetic crystalline assemblies. Coord. Chem. Rev. 2002, 227, 93–127, doi:10.1016/S0010-8545(01)00457-X.
[16]
Papavassiliou, G.C. Tetrachalcogenafulvalenes with four additional heteroatoms. In TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene; Yamada, J.-I., Sugimoto, T., Eds.; Springer: Berlin, Germany, 2004; pp. 35–58.
[17]
Beswick, C.L.; Schulman, J.M.; Stiefel, E.I. Structures and structural trends in homoleptic dithiolene complexes. In Dithiolene Chemistry: Synthesis, Properties, and Applications; Stiefel, E.I., Ed.; John Wiley & Sons: Hoboken, NJ, USA, 2004; Volume 52, pp. 55–110.
[18]
Kirk, M.L.; Mcnaughton, R.L.; Helton, M.E. The electronic structure and spectroscopy of metallo-dithiolene complexes. Prog. Inorg. Chem. 2004, 52, 111–212.
[19]
Wang, K. Electrochemical and chemical reactivity of dithiolene complexes. Prog. Inorg. Chem. 2004, 52, 267–314.
[20]
Faulmann, C.; Cassoux, P. Solid-state properties (electronic, magnetic, optical) of dithiolene complex-based compounds. Prog. Inorg. Chem. 2004, 52, 399–489.
[21]
Kato, R. Conducting metal dithiolene complexes: Structural and electronic properties. Chem. Rev. 2004, 104, 5319–5346, doi:10.1021/cr030655t.
[22]
Fujiwara, E.; Kobayashi, A.; Fujiwara, H.; Kobayashi, H. Syntheses, structures, and physical properties of nickel bis(dithiolene) complexes containing tetrathiafulvalene (TTF) units. Inorg. Chem. 2004, 43, 1122–1129, doi:10.1021/ic034670s. 14753836
[23]
Kobayashi, A.; Fujiwara, E.; Kobayashi, H. Single-component molecular metals with extended-TTF dithiolate ligands. Chem. Rev. 2004, 104, 5243–5264, doi:10.1021/cr030656l.
[24]
Aragoni, M.C.; Arca, M.; Caironi, M.; Denotti, C.; Devillanova, F.A.; Grigiotti, E.; Isaia, F.; Laschi, F.; Lippolis, V.; Natali, D.; et al. Monoreduced [M(R,R' timdt)(2)]-dithiolenes (M = Ni, Pd, Pt; R,R' timdt = disubstituted imidazolidine-2,4,5-trithione): Solid state photoconducting properties in the third optical fiber window. Chem. Commun. 2004. doi:10.1039/B406406B.
[25]
Pearson, C.; Moore, A.J.; Gibson, J.E.; Bryce, M.R.; Petty, M.C. A Field-effect transistor based on Langmuir-Blodgett-films of an Ni(dmit)2 charge-transfer complex. Thin Solid Films 1994, 244, 932–935, doi:10.1016/0040-6090(94)90603-3.
[26]
Tenn, N.; Bellec, N.; Jeannin, O.; Piekara-Sady, L.; Auban-Senzier, P. A single-component molecular metal based on a thiazole dithiolate gold complex. J. Am. Chem. Soc. 2009, 131, 16961–16967, doi:10.1021/ja907426s. 19873973
[27]
Papavassiliou, G.C.; Anyfantis, G.C. Alternative method for the preparation of Ni(dddt)(edt) (dddt = 5,6-dihydro-1,4-dithiin-2,3-dithiolate, edt = cis-1,2-ethylenedithiolate) and similar complexes. Z. Naturforsch. 2005, 60b, 811–813.
[28]
Ji, Y.; Zuo, J.L.; Chen, L.X.; Tian, Y.Q.; Song, Y.L.; Li, Y.Z.; You, X.Z. Synthesis, characterization and optical limiting effect of nickel complexes of multi-sulfur 1,2-dithiolene. J. Phys. Chem. Solids 2005, 66, 207–212, doi:10.1016/j.jpcs.2004.09.015.
[29]
Schiodt, N.C.; Bjornholm, T.; Bechgaard, K.; Neumeier, J.J.; Allgeier, C.; Jacobsen, C.S.; Thorup, N. Structural, electrical, magnetic, and optical properties of bis-benzene-1,2-dithiolato-Au(IV) crystals. Phys. Rev. 1996, 53, 1773–1778, doi:10.1103/PhysRevB.53.1773.
[30]
Papavassiliou, G.C. Design and synthesis of polyheterotetraheterafulvalenes metal 1,2 diheterolenes, and their low-dimensional conducting and superconducting salts. In Lower-Dimensional Systems and Molecular Electronics (NATO Science Series B); Metzger, R.M., Day, P., Papavassiliou, G.C., Eds.; Springer: Berlin, Germany, 1990; pp. 143–162.
[31]
Aragoni, M.C.; Arca, M.; Devillanova, F.A.; Isaia, F.; Lippolis, V.; Mancini, A.; Pala, L.; Slawin, A.M.Z.; Woollins, J.D. [M(R-dmet)2] bis(1,2-dithiolenes): A promising new class intermediate between [M(dmit)2] and [M(R,R'-timdt)2] (M = Ni, Pd, Pt.). Inorg. Chem. 2005, 44, 9610–9612, doi:10.1021/ic051260q. 16363821
[32]
Matsubayashi, G.; Maikawa, T.; Nakano, M. Preparation, spectroscopy and oxidation of [Re(C3S5)3]- and [ReO(C3S5)2]-complexes and crystal-structure of [PPh4][ReO(C3S5)2]. J. Chem. Soc. Dalton Trans. 1993, doi:10.1039/DT9930002995.
[33]
Caironi, M.; Natali, D.; Sampietro, M.; Ward, M.; Meacham, A.; Devillanova, F.A.; Arca, M.; Denotti, C.; Pala, L. Near infrared detection by means of coordination complexes. Synth. Met. 2005, 153, 273–276, doi:10.1016/j.synthmet.2005.07.107.
[34]
Ray, K.; Weyhermuller, T.; Neese, F.; Wieghardt, K. Electronic structure of square planar bis(benzene-1,2-dithiolato)metal complexes [M(L)2]z (z = 2？, 1？, 0; M = Ni, Pd, Pt, Cu, Au): An experimental, density functional, and correlated ab initio study. Inorg. Chem. 2005, 44, 5345–5360, doi:10.1021/ic0507565.
[35]
Tanaka, H.; Okano, Y.; Kobayashi, H.; Suzuki, W.; Kobayashi, A. A three-dimensional synthetic metallic crystal composed of single-component molecules. Science 2001, 291, 285–287, doi:10.1126/science.291.5502.285. 11209074
[36]
Anyfantis, G.C.; Papavassiliou, G.C.; Terzis, A.; Raptopoulou, C.P.; Weng, Y.F.; Yoshino, H.; Murata, K. Preparation and characterization of some nickel 1,2-dithiolene complexes as single-component semiconductors. Z. Naturforsch. 2006, 61b, 1007–1011.
[37]
Anthopoulos, T.D.; Setayesh, S.; Smits, E.; Colle, M.; Cantatore, E.; de Boer, B.; Blom, P.W.M.; de Leeuw, D.M. Air-stable complementary-like circuits based on organic ambipolar transistors. Adv. Mater. 2006, 18, 1900–1904, doi:10.1002/adma.200502677.
[38]
Smits, E.C.P.; Anthopoulos, T.D.; Setayesh, S.; van Veenendaal, E.; Coehoorn, R.; Blom, P.W.M.; de Boer, B.; de Leeuw, D.M. Ambipolar charge transport in organic field-effect transistors. Phys. Rev. 2006, 73, 205316–205321, doi:10.1103/PhysRevB.73.205316.
[39]
Taguchi, T.; Wada, H.; Kambayashi, T.; Noda, B.; Goto, M.; Mori, T.; Ishikawa, K.; Takezoe, H. Comparison of p-type and n-type organic field-effect transistors using nickel coordination compounds. Chem. Phys. Lett. 2006, 421, 395–398, doi:10.1016/j.cplett.2006.01.109.
[40]
Nakano, M.; Kuroda, A.; Matsubayashi, G. Extended bisdithiolene metal complexes: Preparation and electrical conductivities of [M(C8H4S8)2] anion complexes. Inorg. Chim. Acta 1997, 254, 189–193, doi:10.1016/S0020-1693(96)05145-6.
[41]
Marshall, K.L.; Painter, G.; Lotito, K.; Noto, A.G.; Chang, P. Transition metal dithiolene near-IR dyes and their applications in liquid crystal devices. Mol. Cryst. Liqid Crys. 2006, 454, 47–79.
[42]
Barriere, F.; Geiger, W.E. Use of weakly coordinating anions to develop an integrated approach to the tuning of ΔE1/2 values by medium effects. J. Am. Chem. Soc. 2006, 128, 3980–3989, doi:10.1021/ja058171x.
Im, J.U.; Yu, C.Y.; Yoo, J.Y.; Son, S.M.; Lee, G.D.; Park, S.S. A study for microwave enhanced synthesis of NIR absorbing materials. Mater. Sci. Forum 2006, 510–511, 702–705.
[45]
Kobayashi, A.; Okano, Y.; Kobayashi, H. Molecular design and physical properties of single-component molecular metals. J. Phys. Soc. Jpn. 2006, 75, doi:10.1143/JPSJ.75.051002.
Anthopoulos, T.D.; Anyfantis, G.C.; Papavassiliou, G.C.; de Leeuw, D.M. Air-stable ambipolar organic transistors. Appl. Phys. Lett. 2007, 90, doi:10.1080/15421400600697859.
[48]
Anyfantis, G.C.; Papavassiliou, G.C.; Aloukos, P.; Couris, S.; Weng, Y.F.; Yoshino, H.; Murata, K. Unsymmetrical single-component nickel 1,2-dithiolene complexes with extended tetrachalcogenafulvalenedithiolato ligands. Z. Naturforsch. 2007, 62b, 200–204.
[49]
Papavassiliou, G.C.; Anyfantis, G.C.; Koutselas, I.B. Some air-stable unsymmetrical nickel 1,2-dithiolenes with extended tetrathiafulvalenedithiolato ligands. Z. Naturforsch. 2007, 62b, 1481–1486.
[50]
Papavassiliou, G.C.; Anyfantis, G.C.; Steele, B.R.; Terzis, A.; Raptopoulou, C.P.; Tatakis, G.; Chaidogiannos, G.; Glezos, N.; Weng, Y.F.; Yoshino, H.; Murata, K. Some new nickel 1,2-dichalcogenolene complexes as single-component semiconductors. Z. Naturforsch. 2007, 62b, 679–684.
[51]
Saito, G.; Yoshida, Y. Development of conductive organic molecular assemblies: Organic metals, superconductors, and exotic functional materials. Bull. Chem. Soc. Jpn. 2007, 80, 1–137, doi:10.1246/bcsj.80.1.
[52]
Papavassiliou, G.C.; Mousdis, G.A.; Anyfandis, G.C. An improved synthesis of nickel-bis[5,6-dihydro-1,4-dioxine-2,3-dithiolate], Ni(edo)2. Z. Naturforsch. 2002, 57b, 707–708.
[53]
Nunes, J.P.M.; Figueira, M.J.; Belo, D.; Santos, I.C.; Ribeiro, B.; Lopes, E.B.; Henriques, R.T.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C.; et al. Transition metal bisdithiolene complexes based on extended ligands with fused tetrathiafulvalene and thiophene moieties: New single-component molecular metals. Chem. Eur. J. 2007, 13, 9841–9849, doi:10.1002/chem.200701050. 17879249
[54]
Papavassiliou, G.C.; Cotsilios, A.M.; Jacobsen, C.S. Spectroscopic investigation of metal dimercaptodithiolenes and selenium analogs. J. Mol. Struct. 1984, 115, 41–44, doi:10.1016/0022-2860(84)80010-1.
[55]
Eid, S.; Fourmigue, M.; Roisnel, T.; Lorcy, D. Influence of the thiazole backbone on the structural, redox, and optical properties of dithiolene and diselenolene complexes. Inorg. Chem. 2007, 46, 10647–10654, doi:10.1021/ic7013682. 18001113
[56]
Wada, H.; Taguchi, T.; Noda, B.; Kambayashi, T.; Mori, T.; Ishikawa, K.; Takezoe, H. Air stability of n-channel organic transistors based on nickel coordination compounds. Org. Electron. 2007, 8, 759–766, doi:10.1016/j.orgel.2007.06.007.
[57]
Cho, J.Y.; Domercq, B.; Jones, S.C.; Yu, J.; Zhang, X.; An, Z.; Bishop, M.; Barlow, S.; Marder, S.R.; Kippelen, B. High electron mobility in nickel bis(dithiolene) complexes. J. Mater. Chem. 2007, 17, 2642–2647, doi:10.1039/b701036b.
[58]
Cho, J.Y.; Barlow, S.; Marder, S.R.; Fu, J.; Padilha, L.A.; van Stryland, E.W.; Hagan, D.J.; Bishop, M. Strong two-photon absorption at telecommunications wavelengths in nickel bis(dithiolene) complexes. Opt. Lett. 2007, 32, 671–673, doi:10.1364/OL.32.000671. 17308597
[59]
Agostinelli, T.; Caironi, M.; Natali, D.; Sampietro, M.; Arca, M.; Devillanova, F.A.; Ferrero, V. Trapping effects on the frequency response of dithiolene-based planar photodetectors. Synth. Met. 2007, 157, 984–987, doi:10.1016/j.synthmet.2007.10.006.
[60]
Kokatam, S.; Ray, K.; Pap, J.; Bill, E.; Geiger, W.E.; Lesuer, R.J.; Rieger, P.H.; Weyhermuller, T.; Neese, F.; Wieghardt, K. Molecular and electronic structure of square-planar gold complexes containing two 1,2-di(4-tert-butylphenyl)ethylene-1,2-dithiolato ligands: [Au(L？2)2](1+/0/1？/2？). A combined experimental and computational study. Inorg. Chem. 2007, 46, 1100–1111, doi:10.1021/ic061181u. 17291110
[61]
Rabaca, S.; Duarte, M.C.; Santos, I.C.; Fourmigue, M.; Almeida, M. A new approach to divalent thio-azo ligands; Ni(dpesdt)2. Inorg. Chim. Acta 2007, 360, 3797–3801, doi:10.1016/j.ica.2006.12.027.
[62]
Aragoni, M.C.; Arca, M.; Devillanova, F.A.; Isaia, F.; Lippolis, V.; Mancini, A.; Pala, L.; Verani, G.; Agostinelli, T.; Caironi, M.; et al. First example of a near-IR photodetector based on neutral [M(r-dmet)2] bis(1,2-dithiolene) metal complexes. Inorg. Chem. Commun. 2007, 10, 191–194, doi:10.1016/j.inoche.2006.10.019.
[63]
Papavassiliou, G.C.; Anyfantis, G.C.; Terzis, A.; Psycharis, V.; Kyritsis, P.; Paraskevopoulou, P. Some unsymmetrical metal 1,2-dithiolenes based on palladium, platinum and gold. Z. Naturforsch. 2008, 63b, 1377–1382.
[64]
Anyfantis, G.C.; Papavassiliou, G.C.; Assimomytis, N.; Terzis, A.; Psycharis, V.; Raptopoulou, C.P.; Kyritsis, P.; Thoma, V.; Koutselas, I.B. Some unsymmetrical nickel 1,2-dithiolene complexes as candidate materials for optics and electronics. Solid State Sci. 2008, 10, 1729–1733, doi:10.1016/j.solidstatesciences.2008.03.012.
[65]
Stallinga, P.; Benvenho, A.R.V.; Smits, E.C.P.; Mathijssen, S.G.J.; Colle, M.; Gomes, H.L.; de Leeuw, D.M. Determining carrier mobility with a metal-insulator-semiconductor structure. Org. Electron. 2008, 9, 735–739, doi:10.1016/j.orgel.2008.05.007.
[66]
Mori, T. Molecular materials for organic field-effect transistors. J. Phys Condens. Matter 2008, 20, doi:10.1088/0953-8984/20/18/184010.
[67]
Romaniello, P.; Dandria, M.C.; Lelj, F. Nonlinear optical properties of Ni(Me6pzS2))MX (M = Ni, Pd, Pt; X = Me2timdt, mnt). J. Phys. Chem. 2010, 114, 5838–5845, doi:10.1021/jp911353n.
[68]
Bruno, G.; Almeida, M.; Artizzu, F.; Dias, J.C.; Mercuri, M.L.; Pilia, L.; Rovira, C.; Ribas, X.; Serpe, A.; Deplano, P. Innocence and noninnocence of the ligands in bis(pyrazine-2,3-dithiolate and -diselonate) d8-metal complexes. A theoretical and experimental study for the Cu(III), Au(III) and Ni(II) cases. Dalton Trans. 2010, 39, 4566–4574, doi:10.1039/b922626e. 20383385
[69]
Cassoux, P.; Valade, L.; Kobayashi, H.; Kobayashi, A.; Clark, R.A.; Underhill, A.E. Molecular-metals and superconductors derived from metal-complexes of 1,3-dithiol-2-thione-4,5-dithiolate (dmit). Coord. Chem. Rev. 1991, 110, 115–160, doi:10.1016/0010-8545(91)80024-8.
[70]
Anjos, T.; Roberts-Bleming, S.J.; Charlton, A.; Robertson, N.; Mount, A.R.; Coles, S.J.; Hursthouse, M.B.; Kalaji, M.; Murphy, P.J. Nickel dithiolenes containing pendant thiophene units: Precursors to dithiolene-polythiophene hybrid materials. J. Mater. Chem. 2008, 18, 475–483, doi:10.1039/b714372a.
[71]
Kubo, K.; Nakao, A.; Ishii, Y.; Yamamoto, T.; Tamura, M.; Kato, R.; Yakushi, K.; Matsubayashi, G.E. Electrical properties and electronic states of molecular conductors based on unsymmetrical organometallic-dithiolene gold(III) complexes. Inorg. Chem. 2008, 47, 5495–5502, doi:10.1021/ic800176q. 18473455
[72]
Cho, J.Y.; Fu, J.; Padilha, L.A.; Barlow, S.; van Stryland, E.W.; Hagan, D.J.; Bishop, M.; Marder, S.R. Synthesis of a nickel bis(dithiolene) complex with strong near-infrared two-photon absorption. Mol. Cryst. Liqid Cryst. 2008, 485, 915–927, doi:10.1080/15421400801924979.
[73]
Madhu, V.; Das, S.K. New series of asymmetrically substituted bis(1,2-dithiolato)-nickel(III) complexes exhibiting near IR absorption and structural diversity. Inorg. Chem. 2008, 47, 5055–5070, doi:10.1021/ic701408m.
[74]
Sournia-Saquet, A.; Garreau-De Bonneval, B.; Chane-Ching, K.I.; Valade, L. Electrochemical properties and electronic structures of two neutral nickel bis(1,2-dithiolene) complexes. J. Electroanal. Chem. 2008, 624, 84–90, doi:10.1016/j.jelechem.2008.08.001.
Song, I.H.; Rhee, C.H.; Park, S.H.; Lee, S.L.; Grudinin, D.; Song, K.H.; Choe, J. Continuous production of a near infrared absorbing chromophore. Org. Proc. Res. Dev. 2008, 12, 1012–1015, doi:10.1021/op800077j.
[77]
Anyfantis, G.C. Unsymmetrical Metal 1,2-Dithiolenes: Design, Synthesis, Properties and Possible Applications. Ph.D. Thesis, University of Patras, Patras, Greece, 2008.
[78]
Nishikawa, H.; Yasuoka, W.; Sakairi, K.; Oshio, H. Synthesis and physical properties of a new single-component molecular conductor [Au(dhdt)2]. Polyhedron 2009, 28, 1634–1637, doi:10.1016/j.poly.2008.10.012.
Arumugam, K.; Shaw, M.C.; Chandrasekaran, P.; Villagran, D.; Gray, T.G.; Mague, J.T.; Donahue, J.P. Synthesis, structures, and properties of 1,2,4,5-benzenetetrathiolate linked group 10 metal complexes. Inorg. Chem. 2009, 48, 10591–10607, doi:10.1021/ic901257s. 19831407
[82]
Charrier, D.S.H.; de Vries, T.; Mathijssen, S.G.J.; Geluk, E.J.; Smits, E.C.P.; Kemerink, M.; Janssen, R.A.J. Bimolecular recombination in ambipolar organic field effect transistors. Org. Electron. 2009, 10, 994–997, doi:10.1016/j.orgel.2009.03.010.
[83]
Dalgleish, S.; Robertson, N. A stable near IR switchable electrochromic polymer based on an indole-substituted nickel dithiolene. Chem. Commun. 2009, doi:10.1039/B913174D.
[84]
Perochon, R.; Poriel, C.; Jeannin, O.; Piekara-Sady, L.; Fourmigue, M. Chiral, neutral, and paramagnetic gold dithiolene complexes derived from camphorquinone. Eur. J. Inorg. Chem. 2009, 2009, 5413–5421, doi:10.1002/ejic.200900855.
[85]
Serrano-Andres, L.; Avramopoulos, A.; Li, J.B.; Labeguerie, P.; Begue, D.; Kello, V.; Papadopoulos, M.G. Linear and nonlinear optical properties of a series of Ni-dithiolene derivatives. J. Chem. Phys. 2009, 131, doi:10.1063/1.3238234.
[86]
Tamura, M.; Kato, R. Variety of valence bond states formed of frustrated spins on triangular lattices based on a two-level system Pd(dmit)2. Sci. Technol. Adv. Mater. 2009, 10, doi:10.1088/1468-6996/10/2/024304.
[87]
Tenn, N.; Bellec, N.; Jeannin, O.; Piekara-Sady, L.; Auban-Senzier, P.; Iniguez, J.; Canadell, E.; Lorcy, D. A single-component molecular metal based on a thiazole dithiolate gold complex. J. Am. Chem. Soc. 2009, 131, 16961–16967, doi:10.1021/ja907426s. 19873973
[88]
Pilia, L.; Artizzu, F.; Faulmann, C.; Mercuri, M.L.; Serpe, A.; Deplano, P. Square-planar d8 metal push-pull dithiolene complexes: Synthesis and characterization of [Pd(Me2pipdt)(dmit)]. Inorg. Chem. Commun. 2009, 12, 490–493, doi:10.1016/j.inoche.2009.04.001.
Zhou, B.; Kobayashi, A.; Okano, Y.; Nakashima, T.; Aoyagi, S.; Nishibori, E.; Sakata, M.; Tokumoto, M.; Kobayashi, H. Single-component molecular conductor [Pt(tmdt)(2)] (tmdt = trimethylenetetrathiafulvalenedithiolate)—An advanced molecular metal exhibiting high metallicity. Adv. Mater. 2009, 21, 3596–3600, doi:10.1002/adma.200803116.
[91]
Bruno, G.; Almeida, M.; Simao, D.; Mercuri, M.L.; Pilia, L.; Serpe, A.; Deplano, P. Peculiar electronic and vibrational properties of metal-dithiolenes (Ni, Au) based on 1,2,5-thiadiazole-3,4-dithiolato. Dalton Trans. 2009, doi:10.1039/B812214H.
[92]
Soras, G.; Psaroudakis, N.; Manos, M.J.; Tasiopoulos, A.J.; Liakos, D.G.; Mousdis, G.A. New type dithiolene complex based on 4,5-(1,4-dioxane-2,3-diyldithio)-1,3-dithiol ligand: Synthesis, experimental and theoretical investigation. Polyhedron 2009, 28, 3340–3348, doi:10.1016/j.poly.2009.05.031.
[93]
Dalgleish, S.; Yoshikawa, H.; Matsushita, M.M.; Awaga, K.; Robertson, N. Electrodeposition as a superior route to a thin film molecular semiconductor. Chem. Sci. 2011, 2, 316–320, doi:10.1039/c0sc00446d.
[94]
Anyfantis, G.C.; Papavassiliou, G.C.; Terzis, A.; Raptopoulou, C.P.; Psycharis, V.; Paraskevopoulou, P. Preparation and characterization of Ni(dpedt)(pddt) and Ni(dpedt)(pddt)·CS2, where dpedt is diphenylethylenedithiolate and pddt is 6,7-dihydro-5H-1,4-dithiepin-2,3-dithiolate. Polyhedron 2010, 29, 969–974, doi:10.1016/j.poly.2009.11.014.
[95]
Deplano, P.; Pilia, L.; Espa, D.; Mercuri, M.L.; Serpe, A. Square-planar d8 metal mixed-ligand dithiolene complexes as second order nonlinear optical chromophores: Structure/property relationship. Coord. Chem. Rev. 2009, 254, 1434–1447.
[96]
Ambrosio, L.; Aragoni, M.C.; Arca, M.; Devillanova, F.A.; Hursthouse, M.B.; Huth, S.L.; Isaia, F.; Lippolis, V.; Mancini, A.; Pintus, A. Synthesis and characterization of novel gold(III) complexes of asymmetrically aryl-substituted 1,2-dithiolene ligands featuring potential-controlled spectroscopic properties. Chem. Asian J. 2010, 5, 1395–1406. 20419725
[97]
Rabaca, S.; Almeida, M. Dithiolene complexes containing n coordinating groups and corresponding tetrathiafulvalene donors. Coord. Chem. Rev. 2010, 254, 1493–1508, doi:10.1016/j.ccr.2009.12.006.
[98]
Basu, P.; Nigam, A.; Mogesa, B.; Denti, S.; Nemykin, V.N. Synthesis, characterization, spectroscopy, electronic and redox properties of a new nickel dithiolene system. Inorg. Chim. Acta 2010, 363, 2857–2864, doi:10.1016/j.ica.2010.04.004.
[99]
Aloukos, P.; Chatzikyriakos, G.; Papagiannouli, I.; Liaros, N.; Couris, S. Transient nonlinear optical response of some symmetrical nickel dithiolene complexes. Chem. Phys. Lett. 2010, 495, 245–250 and references therein, doi:10.1016/j.cplett.2010.06.072.
[100]
Soras, G.; Psaroudakis, N.; Mousdis, G.A.; Manos, M.J.; Tasiopoulos, A.J.; Aloukos, P.; Couris, S.; Labeguerie, P.; Lipinski, J.; Avramopoulos, A.; et al. Synthesis and non-linear optical properties of some novel nickel derivatives. Chem. Phys. 2010, 372, 33–45, doi:10.1016/j.chemphys.2010.04.019.
[101]
Bui, T.T.; Garreau-De Bonneval, B.; Ching, K. Synthesis and preliminary physical properties of new neutral tetraalkoxy-substituted nickel bis(1,2-dithiolene) complexes. New J. Chem. 2010, 34, 337–347, doi:10.1039/b9nj00519f.
[102]
Garreau-De Bonneval, B.; Ching, K.; Alary, F.; Bui, T.T.; Valade, L. Neutral d8 metal bis-dithiolene complexes: Synthesis, electronic properties and applications. Coord. Chem. Rev. 2010, 254, 1457–1467, doi:10.1016/j.ccr.2010.02.019.
[103]
Chatzikyriakos, G.; Papagiannouli, I.; Couris, S.; Anyfantis, G.C.; Papavassiliou, G.C. Nonlinear optical response of a symmetrical au dithiolene complex under ps and ns laser excitation in the infrared and in the visible. Chem. Phys. Lett. 2011, 513, 229–235, doi:10.1016/j.cplett.2011.07.091.
[104]
Aragoni, M.C.; Arca, M.; Devillanova, F.A.; Isaia, F.; Lippolis, V.; Pintus, A. Gold(III) complexes of asymmetrically aryl-substituted 1,2-dithiolene ligands featuring potential-controlled spectroscopic properties: An insight into the electronic properties of bis(pyren-1-yl-ethylene-1,2-dithiolato)gold(III). Chem. Asian J. 2011, 6, 198–208, doi:10.1002/asia.201000525.
[105]
Takahashi, Y.; Hasegawa, T.; Papavassiliou, G.C.; Anyfantis, G.C. Single crystal FETs based on metal 1,2-dithiolenes. National Hellenic Research Foundation, Greece, 2012. Unpublished Work.
[106]
Pilia, L.; Espa, D.; Barsella, A.; Fort, A.; Makedonas, C.; Marchio, L.; Mercuri, M.L.; Serpe, A.; Mitsopoulou, C.A.; Deplano, P. Combined experimental and theoretical study on redox-active d8 metal dithione-dithiolato complexes showing molecular second-order nonlinear optical activity. Inorg. Chem. 2011, 50, 10015–10027, doi:10.1021/ic2007765. 21939192
[107]
Mori, T. Organic charge-transfer salts and the component molecules in organic transistors. Chem. Lett. 2011, 40, 428–434, doi:10.1246/cl.2011.428.
Dalgleish, S.; Labram, J.G.; Li, Z.; Wang, J.P.; Mcneill, C.R.; Anthopoulos, T.D.; Greenham, N.C.; Robertson, N. Indole-substituted nickel dithiolene complexes in electronic and optoelectronic devices. J. Mater. Chem. 2011, 21, 15422–15430, doi:10.1039/c1jm12466h.
[114]
Hu, L.; Qin, J.; Zhou, N.; Meng, Y.-F.; Xu, Y.; Zuo, J.-L.; You, X.-Z. Synthesis, characterization, and optical properties of new metal complexes with the multi-sulfur 1,2-dithiolene ligand. Dye. Pigment. 2012, 92, 1223–1230, doi:10.1016/j.dyepig.2011.08.003.
[115]
Stout, G.H.; Jensen, L.H. X-Ray Structure Determination, 2nd ed.; John Wiley & Sons: Hoboken, NJ, USA, 1989; p. 74. Chapter 4.
[116]
Kalb, W.L.; Mattenberger, K.; Batlogg, B. Oxygen-related traps in pentacene thin films: Energetic position and implications for transistor performance. Phys. Rev. 2008, 78, doi:10.1103/PhysRevB.78.035334.
Papavassiliou, G.C. Optical-properties of small inorganic and organic metal particles. Prog. Solid State Chem. 1979, 12, 185–271, doi:10.1016/0079-6786(79)90001-3.
[119]
Papavassiliou, G.C. Three- and low-dimensional inorganic semiconductors. Prog. Solid State Chem. 1997, 25, 125–270, doi:10.1016/S0079-6786(97)80886-2.
Rozhin, A.G.; Scardaci, V.; Wang, F.; Hennrich, F.; White, I.H.; Milne, W.I.; Ferrari, A.C. Generation of ultra-fast laser pulses using nanotube mode-lockers. Phys. Status Solidi B 2006, 243, 3551–3555, doi:10.1002/pssb.200669151.
[122]
Ward, M.D. Electrochemical Aspects of Low-Dimensional Molecular Solids. In Electroanalytical Chemistry; Bard, A.J., Ed.; Dekker: New York, NY, USA, 1988; Volume 16, pp. 182–299.
Podzorov, V.; Pudalov, V.M.; Gershenson, M.E. Field-effect transistors on rubrene single crystals with parylene gate insulator. Appl. Phys. Lett. 2003, 82, 1739–1741, doi:10.1063/1.1560869.
[125]
Wan, A.; Hwang, J.; Amy, F.; Kahn, A. Impact of electrode contamination on the α-NPD/Au hole injection barrier. Org. Electron. 2005, 6, 47–54, doi:10.1016/j.orgel.2005.02.003.
[126]
Qiao, Y.; Zhang, J.; Xu, W.; Zhu, D. Incorporation of pyrrole to oligothiophene-based quinoids end capped with dicyanomethylene: A new class of solution processable n-channel organic semiconductors for air-stable organic field-effect transistors. J. Mater. Chem. 2012. in press.
[127]
Kahn, A.; Koch, N.; Gao, W.Y. Electronic structure and electrical properties of interfaces between metals and pi-conjugated molecular films. J. Polym. Sci. B Polym Phys. 2003, 41, 2529–2548, doi:10.1002/polb.10642.
[128]
Braun, S.; Salaneck, W.R.; Fahlman, M. Energy-level alignment at organic/metal and organic/organic interfaces. Adv. Mater. 2009, 21, 1450–1472, doi:10.1002/adma.200802893.
[129]
Rhee, S.W.; Yun, D.J. Metal-semiconductor contact in organic thin film transistors. J. Mater. Chem. 2008, 18, 5437–5444, doi:10.1039/b805884a.
[130]
Papavassiliou, G.C.; Kakoussis, V.C.; Lagouvardos, D.J. Preparation of some bis(alkylthio)-bis(alkylseleno)tetrathiafulvalenes. Z. Naturforsch. 1991, 46b, 1269–1271.
[131]
Papavassiliou, G.C.; Lagouvardos, D.J.; Kakoussis, V.C. 5,6-Ethylenediseleno-1,3-dithiolo[4,5-b] [1,4]dithiin-2-thione as starting material for the preparation of new tetrathiafulvalenes. Z. Naturforsch. 1991, 46b, 1730–1732.
[132]
Papavassiliou, G.C.; Misaki, Y.; Takahashi, K.; Yamada, J.; Mousdis, G.A.; Sharahata, T.; Ise, T. New pi-donor molecules with a pyrazino group and their conducting salts. Z. Naturforsch. 2001, 56b, 297–300.
[133]
Yamada, J.-I.; Sugimoto, T. TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene; Springer: Berlin, Germany, 2004.
Takahashi, Y.; Hasegawa, J.; Abe, Y.; Tokura, Y.; Nishimura, K.; Saito, G. Tuning of electron injections for n-type organic transistor based on charge-transfer compounds. Appl. Phys. Lett. 2005, 86, doi:10.1063/1.1863434.
[136]
Takahashi, Y.; Hasegawa, T.; Abe, Y.; Tokura, Y.; Saito, G. Organic metal electrodes for controlled p- and n-type carrier injections in organic field-effect transistors. Appl. Phys. Lett. 2006, 88, doi:10.1063/1.2173226.
[137]
Takahashi, Y.; Hasegawa, T.; Horiuchi, S.; Kumai, R.; Tokura, Y.; Saito, G. High mobility organic field-effect transistor based on hexamethylenetetrathiafulvalene with organic metal electrodes. Chem. Mater. 2007, 19, 6382–6384, doi:10.1021/cm702690w.
[138]
Hiraoka, M.; Hasegawa, T.; Yamada, T.; Takahashi, Y.; Horiuchi, S.; Tokura, Y. On-substrate synthesis of molecular conductor films and circuits. Adv. Mater. 2007, 19, 3248–3251, doi:10.1002/adma.200701162.
[139]
Haas, S.; Takahashi, Y.; Takimiya, K.; Hasegawa, T. High-performance dinaphtho-thieno-thiophene single crystal field-effect transistors. Appl. Phys. Lett. 2009, 95, doi:10.1063/1.3183509.
