A family of solution processable ligands and their Re(I) complexes towards light emitting applications

Wrighton, 1974, Nature of the lowest excited state in tricarbonylchloro-1,10-phenanthrolinerhenium(I) and related complexes, J Am Chem Soc, 96, 998, 10.1021/ja00811a008 Takeda, 2008, Development of an efficient photocatalytic system for co2 reduction using rhenium(i) complexes based on mechanistic studies, J Am Chem Soc, 130, 2023, 10.1021/ja077752e Grills, 2010, New directions for the photocatalytic reduction of CO2: supramolecular, scCO2 or biphasic ionic liquid−scCO2 systems, J Phys Chem Lett, 1, 2709, 10.1021/jz1010237 Abdel-Shafi, 2007, Photosensitized generation of singlet oxygen from rhenium(I) and iridium(III) complexes, Dalton Trans, 2510, 10.1039/b705524b Belliston-Bittner, 2005, Picosecond photoreduction of inducible nitric oxide synthase by rhenium(I)−diimine wires, J Am Chem Soc, 127, 15907, 10.1021/ja0543088 Sato, 2015, Photochemical reactions of fac-rhenium(I) tricarbonyl complexes and their application for synthesis, Coord Chem Rev, 282–283, 50, 10.1016/j.ccr.2014.05.009 Ng, 2011, Luminescent rhenium(I) complexes with acetylamino- and trifluoroacetylamino-containing phenanthroline ligands: anion-sensing study, Dalton Trans, 40, 10020, 10.1039/c1dt10831j Lo, 2010, vol. 254, 2603 Xu, 2014, Study on an oxygen sensing rhenium(I) complex with enlarged sensing/active area: fabrication, photophysical parameters and molecular oxygen sensing performance, Spectrochim Acta A Mol Biomol Spectrosc, 123, 369, 10.1016/j.saa.2013.12.055 Ramdass, 2017, Recent developments on optical and electrochemical sensing of copper(II) ion based on transition metal complexes, Coord Chem Rev, 343, 278, 10.1016/j.ccr.2017.06.002 Ramdass, 2017, Luminescent sensor for copper(II) ion based on imine functionalized monometallic rhenium(I) complexes, Sensor Actuator B Chem, 240, 1216, 10.1016/j.snb.2016.09.073 Lees, 1998, Organometallic complexes as luminescence probes in monitoring thermal and photochemical polymerizations, Coord Chem Rev, 177, 3, 10.1016/S0010-8545(98)00099-X Lees, 1995, The luminescence rigidochromic effect exhibited by organometallic complexes: rationale and applications, Comments Mod Chem, 17, 319 Moore, 2011, On the causes of altered photophysics of luminescent metal complexes embedded in polymer hosts, Langmuir, 27, 9567, 10.1021/la201432w Zhao, 2010, Phosphorescent chemosensors based on heavy-metal complexes, Chem Soc Rev, 39, 3007, 10.1039/b915340c Fernández-Acebes, 1999, Optical switching and fluorescence modulation properties of photochromic metal complexes derived from dithienylethene ligands, Chem Eur J, 5, 3285, 10.1002/(SICI)1521-3765(19991105)5:11<3285::AID-CHEM3285>3.0.CO;2-Q Sun, 2000, Photoswitchable trinuclear transition-metal complexes. Intramolecular triplet–triplet energy transfer from fac-(diimine)ReI(CO)3 chromophores to a stilbene-like bridging ligand, Chem Commun, 201, 10.1039/a908074k Lewis, 2000, Proton-controlled photoisomerization: rhenium(I) tricarbonyl bipyridine linked to amine or azacrown ether groups by a styryl pyridine bridging ligand, Chem Commun, 1865, 10.1039/b005889k Sathish, 2015, Aggregation-induced phosphorescence enhancement (AIPE) based on transition metal complexes–an overview, J Photochem Photobiol C Photochem Rev, 23, 25, 10.1016/j.jphotochemrev.2015.04.001 Yam, 1999, Luminescent rhenium(I) carbon wires:  synthesis, photophysics, and electrochemistry. X-ray crystal structure of [Re(tBu2bpy)(CO)3(C⋮CC⋮C)Re(tBu2bpy)(CO)3], Organometallics, 18, 5252, 10.1021/om990512q Bourgault, 1998, Synthesis and molecular hyperpolarisabilities of donor–acceptor bipyridyl metal complexes (M=Re, Zn, Hg), New J Chem, 22, 517, 10.1039/a708750k Zhang, 2007, Synthesis, characterization, Langmuir−blodgett film-forming property, and second-order nonlinear optical study of rhenium(I) and ruthenium(ii) diimine complexes, Organometallics, 26, 5423, 10.1021/om070030b Oriskovich, 1995, Luminescent labels for purine nucleobases: electronic properties of guanine bound to rhenium(I), Inorg Chem, 34, 29, 10.1021/ic00111a001 Stoeffler, 1995, Unusual photophysics of a rhenium(I) dipyridophenazine complex in homogeneous solution and bound to DNA, J Am Chem Soc, 117, 7119, 10.1021/ja00132a012 Yam, 1997, Deoxyribonucleic acid binding and photocleavage studies of rhenium(I) dipyridophenazine complexes, J Chem Soc Dalton Trans, 2067 Ismail, 2017, Synthesis, characterization and DNA interaction studies of tricarbonyl rhenium(I) compounds containing terpyridine Schiff base chelates, J Organomet Chem, 833, 1, 10.1016/j.jorganchem.2017.01.017 Barbazán, 2010, Tricarbonyl rhenium(I) and technetium(I) complexes with hydrazones derived from 4,5‐diazafluoren‐9‐one and 1,10‐phenanthroline‐5,6‐dione, Eur J Inorg Chem, 4622, 10.1002/ejic.201000522 Tzanopoulou, 2006, Synthesis, Characterization, and Biological Evaluation of M(I)(CO)3(NNO) Complexes (M = Re, 99mTc) conjugated to 2-(4-aminophenyl)benzothiazole as potential breast cancer radiopharmaceuticals, J Med Chem, 49, 5408, 10.1021/jm0606387 Fuks, 2008, Structural features of tricarbonyl(N-methyl-2-pyridinecarboxyamide)chloro-rhenium(I)-potential precursor of radiopharmaceuticals, Polyhedron, 27, 1353, 10.1016/j.poly.2007.12.031 Leonidova, 2014, Underestimated potential of organometallic rhenium complexes as anticancer agents, ACS Chem Biol, 9, 2180, 10.1021/cb500528c Knopf, 2017, Underestimated potential of organometallic rhenium complexes as anticancer agents, J Am Chem Soc, 139, 14302, 10.1021/jacs.7b08640 Marker, 2018, Photoactivated in vitro anticancer activity of rhenium(I) tricarbonyl complexes bearing water-soluble phosphines, Inorg Chem, 57, 1311, 10.1021/acs.inorgchem.7b02747 Yang, 2017, Simultaneously inducing and tracking cancer cell metabolism repression by mitochondria-immobilized rhenium(I) complex, ACS Appl Mater Interfaces, 9, 13900, 10.1021/acsami.7b01764 Choi, 2015, Modification of 1,2,4,5-tetrazine with cationic rhenium(I) polypyridine units to afford phosphorogenic bioorthogonal probes with enhanced reaction kinetics, Chem Commun, 51, 3442, 10.1039/C4CC09532D Lo, 2016, vol. 68, 97 Balasingham, 2012, Biologically compatible, phosphorescent dimetallic rhenium complexes linked through functionalized alkyl chains: syntheses, spectroscopic properties, and applications in imaging microscopy, Inorg Chem, 51, 1419, 10.1021/ic201654d Lee, 2007, Metal coordination-assisted near-infrared photochromic behavior:  a large perturbation on absorption wavelength properties of n,n-donor ligands containing diarylethene derivatives by coordination to the rhenium(I) metal center, J Am Chem Soc, 129, 6058, 10.1021/ja067425r Sun, 2002, Synthesis, photophysical properties, and photoinduced luminescence switching of trinuclear diimine rhenium(I) tricarbonyl complexes linked by an isomerizable stilbene-like ligand, Organometallics, 21, 39, 10.1021/om0106027 Yam, 2004, Photochromic and luminescence switching properties of a versatile diarylethene-containing 1,10-phenanthroline ligand and its rhenium(I) complex, J Am Chem Soc, 126, 12734, 10.1021/ja047446q Yam, 2000, Syntheses, crystal structure, and photochromic properties of rhenium(I) complexes containing the spironaphthoxazine moiety, Organometallics, 19, 1820, 10.1021/om991009g Yue, 2007, Rhenium(I) complex as an electron acceptor in a photovoltaic device, J Alloy Comp, 432, L15, 10.1016/j.jallcom.2006.06.012 Mak, 2009, The use of sublimable chlorotricarbonyl bis(phenylimino)acenaphthene rhenium(I) complexes as photosensitizers in bulk-heterojunction photovoltaic devices, Organomet Energy Convers, 694, 2770 Liu, 2012, Highly efficient organic ultraviolet photodetectors based on Re(I) complexes, Chem Res Chin Univ, 28, 503 Veronese, 2016, New dinuclear hydrido-carbonyl rhenium complexes designed as photosensitizers in dye-sensitized solar cells, New J Chem, 40, 2910, 10.1039/C5NJ03000E Zhao, 2016, Recent advances of neutral rhenium(I) tricarbonyl complexes for application in organic light-emitting diodes, Synth Met, 212, 131, 10.1016/j.synthmet.2015.12.014 Hu, 2017, New rhenium(I) complex with thiadiazole-annelated 1,10-phenanthroline for highly efficient phosphorescent OLEDs, Dyes Pigments, 137, 569, 10.1016/j.dyepig.2016.10.048 Klemens, 2016, Rhenium(I) terpyridine complexes – synthesis, photophysical properties and application in organic light emitting devices, Dalton Trans, 45, 1746, 10.1039/C5DT04093K Klemens, 2016, Synthesis, photophysical properties and application in organic light emitting devices of rhenium(I) carbonyls incorporating functionalized 2,2′:6′,2′′-terpyridines, RSC Adv, 6, 56335, 10.1039/C6RA08981J Wang, 2013, Synthesis and photoluminescence properties of rhenium(I) complexes based on 2,2′:6′,2′′-terpyridine derivatives with hole-transporting units, Dalton Trans, 42, 2716, 10.1039/C2DT32154H Black, 2012, Preparation and characterization of rhenium(I) dicarbonyl complexes based on the meridionally-coordinated terpyridine ligand, Inorg Chem Commun, 24, 16, 10.1016/j.inoche.2012.07.034 Frenzel, 2013, Synthesis, spectroscopic, electrochemical and computational studies of rhenium(I) dicarbonyl complexes based on meridionally-coordinated 2,2′:6′,2′′-terpyridine, Dalton Trans, 42, 12440, 10.1039/c3dt51251g Thorp-Greenwood, 2016, Tris(rhenium fac-tricarbonyl) polypyridine functionalized cyclotriguaiacylene ligands with rich and varied emission, Organometallics, 35, 1632, 10.1021/acs.organomet.6b00099 Amoroso, 2010, Functionalisation of terpyridine complexes containing the Re(CO)3+ moiety, Dalton Trans, 39, 6993, 10.1039/c0dt00174k Coogan, 2009, A Rhenium Tricarbonyl 4′‐oxo‐terpy trimer as a luminescent molecular vessel with a removable silver stopper, Angew Chem Int Ed, 48, 4965, 10.1002/anie.200900981 Laramee-Milette, 2015, Synthesis of discrete Re(I) di- and tricarbonyl assemblies using a [4 × 1] directional bonding strategy, Dalton Trans, 44, 41, 10.1039/C4DT03077J Laramée-Milette, 2017, Synthesis of single and double dibenzohelicenes by rhodium‐catalyzed intramolecular [2+2+2] and [2+1+2+1] cycloaddition, Chem Eur J, 23, 6370, 10.1002/chem.201700077 Klemens, 2017, Synthesis, spectroscopic, electrochemical and computational studies of rhenium(i) tricarbonyl complexes based on bidentate-coordinated 2,6-di(thiazol-2-yl)pyridine derivatives, Dalton Trans, 46, 9605, 10.1039/C7DT01948C Zhang, 2011, Ligand effects on structures and spectroscopic properties of pyridine-2-aldoxime complexes of Re(CO)3+: DFT/TDDFT theoretical studies, J Phys Chem A, 115, 3174, 10.1021/jp200872b Velmurugan, 2014, Are Re(I) phenanthroline complexes suitable candidates for OLEDs? Answers from DFT and TD-DFT investigations, PhysChemChemPhys, 16, 21157 Zhao, 2012, A rhenium(I) complex with indolyl-containing ligand: synthesis, photophysical properties and theoretical studies, Inorg Chim Acta, 387, 100, 10.1016/j.ica.2012.01.001 Xia, 2013, Electronic structures and spectral properties of rhenium(I) tricarbonyl cyclopenta[b]dipyridine complexes containing different aromatic ring groups, J Organomet Chem, 727, 10, 10.1016/j.jorganchem.2012.12.024 Velmurugan, 2015, Luminescent Re(I) terpyridine complexes for OLEDs: what does the DFT/TD-DFT probe reveal?, Dalton Trans, 44, 8529, 10.1039/C4DT02917H Maroń, 2016, Tuning the photophysical properties of 4′-substituted terpyridines – an experimental and theoretical study, Org Biomol Chem, 14, 10.1039/C6OB00038J 2011 Sheldrick, 2008, A short history of SHELX, Acta Crystallogr A, 64, 112, 10.1107/S0108767307043930 Frisch, 2009 Perdew, 1996, Generalized gradient approximation made simple, Phys Rev Lett, 77, 3865, 10.1103/PhysRevLett.77.3865 Adamo, 1999, Toward reliable density functional methods without adjustable parameters: the PBE0 model, J Chem Phys, 110, 6158, 10.1063/1.478522 Weigend, 2005, Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy, Phys Chem Chem Phys, 7, 3297, 10.1039/b508541a Rappoport, 2010, Property-optimized Gaussian basis sets for molecular response calculations, J Chem Phys, 133, 134105, 10.1063/1.3484283 Andrae, 1990, Energy-adjusted ab initio pseudopotentials for the second and third row transition elements, Theor Chim Acta, 77, 123, 10.1007/BF01114537 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys Rev B, 37, 785, 10.1103/PhysRevB.37.785 Stephens, 1994, Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields, J Phys Chem, 98, 11623, 10.1021/j100096a001 Vosko, 1980, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Can J Phys, 58, 1200, 10.1139/p80-159 Becke, 1992, Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction, J Chem Phys, 96, 2155, 10.1063/1.462066 Ditchfield, 1971, Self‐consistent molecular‐orbital methods. IX. An extended Gaussian‐type basis for molecular‐orbital studies of organic molecules, J Chem Phys, 54, 724, 10.1063/1.1674902 Hariharan, 1973, The influence of polarization functions on molecular orbital hydrogenation energies, Theor Chim Acta, 28, 213, 10.1007/BF00533485 Clark, 1983, Efficient diffuse function‐augmented basis sets for anion calculations. III. The 3‐21+G basis set for first‐row elements, Li–F, J Comput Chem, 4, 294, 10.1002/jcc.540040303 Hehre, 1972, Self–consistent molecular orbital methods. XII. Further extensions of Gaussian–type basis sets for use in molecular orbital studies of organic molecules, J Chem Phys, 56, 2257, 10.1063/1.1677527 Cancès, 1997, A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics, J Chem Phys, 107, 3032, 10.1063/1.474659 Mennucci, 1997, Continuum solvation models: a new approach to the problem of solute's charge distribution and cavity boundaries, J Chem Phys, 106, 5151, 10.1063/1.473558 Cossi, 1998, Ab initio study of ionic solutions by a polarizable continuum dielectric model, Chem Phys Lett, 286, 253, 10.1016/S0009-2614(98)00106-7 Cardona, 2011, Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications, Adv Mater, 23, 2367, 10.1002/adma.201004554 Bujak, 2013, Polymers for electronics and spintronics, Chem Soc Rev, 42, 8895, 10.1039/c3cs60257e Juris, 1988, Synthesis and photophysical and electrochemical properties of new halotricarbonyl(polypyridine)rhenium(I) complexes, Inorg Chem, 27, 4007, 10.1021/ic00295a022 Yang, 2015, DFT/TDDFT studies of the ancillary ligand effects on structures and photophysical properties of rhenium(I) tricarbonyl complexes with the imidazo[4,5‐f]‐1,10‐phenanthroline ligand, Int J Quant Chem, 115, 1467, 10.1002/qua.24951 Mutai, 2001, Phenyl-substituted 2,2′:6′,2″-terpyridine as a new series of fluorescent compounds–their photophysical properties and fluorescence tuning, J Chem Soc Perkin Trans, 2, 1045, 10.1039/b102685m Itoh, 2012, Correction to fluorescence and phosphorescence from higher excited states of organic molecules, Chem Rev, 112, 4541, 10.1021/cr200166m Świtlicka, 2016, Rhenium(I) complexes with phenanthrolines bearing electron-withdrawing Cl and electron-donating CH3 substituents – synthesis, photophysical, thermal, and electrochemical properties with electroluminescence ability, RSC Adv, 6, 112908, 10.1039/C6RA23935H