The Journal of Physical Chemistry A
Article
Isoenergetic MLCT and Ligand Localized Excited States. Coord. Chem.
Rev. 1998, 171, 43−59.
(44) Nelsen, S. F. Electron Transfer Reactions Within Sigma- and Pi-
Bridged Dinitrogen-Centered Intervalence Radical Cations. Adv. Phys.
Organ. Chem. 2006, 41, 183−215.
(45) Luo, P.; Feinberg, A. M.; Guirado, G.; Farid, S.; Dinnocenzo, J.
P. Accurate Oxidation Potentials of 40 Benzene and Biphenyl
Derivatives with Heteroatom Substituents. J. Org. Chem. 2014, 79,
9297−9304.
(26) Schlundt, S.; Kuzmanich, G.; Spanig, F.; Rojas, G. D.; Kovacs,
C.; Garcia-Garibay, M. A.; Guldi, D. M.; Hirsch, A. Dendritic
Porphyrin-Fullerene Conjugates: Efficient Light-Harvesting and
Charge-Transfer Events. Chem.Eur. J. 2009, 15, 12223−12233.
(27) Siebert, R.; Akimov, D.; Schmitt, M.; Winter, A.; Schubert, U. S.;
Dietzek, B.; Popp, J. Spectroscopic Investigation of the Ultrafast
Photoinduced Dynamics in pi-Conjugated Terpyridines. ChemPhy-
sChem 2009, 10, 910−919.
(46) Zweig, A.; Hodgson, W. G.; Jura, W. H. Oxidation of
Methoxybenzenes. J. Am. Chem. Soc. 1964, 86, 4124−&.
(47) Gonzalez, M. T.; Zhao, X. T.; Manrique, D. Z.; Miguel, D.;
Leary, E.; Gulcur, M.; Batsanov, A. S.; Rubio-Bollinger, G.; Lambert,
C. J.; Bryce, M. R.; et al. Structural versus Electrical Functionalization
of Oligo(phenylene ethynylene) Diamine Molecular Junctions. J. Phys.
Chem. C 2014, 118, 21655−21662.
(28) Vail, S. A.; Krawczuk, P. J.; Guldi, D. M.; Palkar, A.; Echegoyen,
L.; Tome, J. P. C.; Fazio, M. A.; Schuster, D. I. Energy and Electron
Transfer in Polyacetylene-Linked Zinc-Porphyrin-[60]Fullerene Mo-
lecular Wires. Chem.Eur. J. 2005, 11, 3375−3388.
(29) Melomedov, J.; Ochsmann, J. R.; Meister, M.; Laquai, F.;
Heinze, K. Tuning Reductive and Oxidative Photoinduced Electron
Transfer in Amide-Linked Anthraquinone-Porphyrin-Ferrocene Archi-
tectures. Eur. J. Inorg. Chem. 2014, 2014, 1984−2001.
(48) Walther, M. E.; Wenger, O. S. Hole Tunneling and Hopping in
a Ru(bpy)32+-Phenothiazine Dyad with a Bridge Derived from Oligo-
p-Phenylene. Inorg. Chem. 2011, 50, 10901−10907.
(49) Benniston, A. C.; Harriman, A. Charge on the Move: How
Electron-Transfer Dynamics Depend on Molecular Conformation.
Chem. Soc. Rev. 2006, 35, 169−179.
(30) Van Wallendael, S.; Rillema, D. P. Photoinduced Intramolecular
Energy-Transfer from One Metal Center to the Other in a Mixed-
Metal Ruthenium-Rhenium Complex. Coord. Chem. Rev. 1991, 111,
297−318.
(50) Lortscher, E.; Elbing, M.; Tschudy, M.; von Hanisch, C.; Weber,
̈
̈
H. B.; Mayor, M.; Riel, H. Charge Transport through Molecular Rods
with Reduced pi-Conjugation. ChemPhysChem 2008, 9, 2252−2258.
(51) Hanss, D.; Wenger, O. S. Conformational Effects on Long-
Range Electron Transfer: Comparison of Oligo-p-Phenylene and
Oligo-p-Xylene Bridges. Eur. J. Inorg. Chem. 2009, 3778−3790.
(31) Bauerle, P.; Segelbacher, U.; Gaudl, K. U.; Huttenlocher, D.;
̈
Mehring, M. Didodecylsexithiophene a Model-Compound for the
Formation and Characterization of Charge-Carriers in Conjugated
Chains. Angew. Chem., Int. Ed. 1993, 32, 76−78.
(32) He, J.; Chen, F.; Liddell, P. A.; Andreasson, J.; Straight, S. D.;
Gust, D.; Moore, T. A.; Moore, A. L.; Li, J.; Sankey, O. F.; et al.
Switching of a Photochromic Molecule on Gold Electrodes: Single-
Molecule Measurements. Nanotechnology 2005, 16, 695−702.
(33) Liddell, P. A.; Kodis, G.; Moore, A. L.; Moore, T. A.; Gust, D.
Photonic Switching of Photoinduced Electron Transfer in a
Dithienylethene-Porphyrin-Fullerene Triad Molecule. J. Am. Chem.
Soc. 2002, 124, 7668−7669.
́ ́
(52) Viault, G.; Gree, D.; Das, S.; Yadav, J. S.; Gree, R. Synthesis of a
Focused Chemical Library Based on Derivatives of Embelin, a Natural
Product with Proapoptotic and Anticancer Properties. Eur. J. Org.
Chem. 2011, 1233−1241.
(53) Staab, H. A.; Weiser, J.; Futscher, M.; Voit, G.; Ruckemann, A.;
Anders, C. Porphyrin-Quinone Cyclophanes with Gradually Varied
Acceptor Strength - Syntheses and Characterizations. Chem. Ber. 1992,
125, 2285−2301.
(34) Zhou, G.; Baumgarten, M.; Mullen, K. Arylamine-Substituted
(54) Poigny, S.; Guyot, M.; Samadi, M. Total Synthesis of Maesanin
and Analogues. Tetrahedron 1998, 54, 14791−14802.
̈
Oligo(Ladder-Type Pentaphenylene)s: Electronic Communication
Between Bridged Redox Centers. J. Am. Chem. Soc. 2007, 129,
12211−12221.
(55) Shu, W. F.; Guan, C. W.; Guo, W. H.; Wang, C. Y.; Shen, Y. J.
Conjugated Poly(Aryleneethynylenesiloles) and Their Application in
Detecting Explosives. J. Mater. Chem. 2012, 22, 3075−3081.
(56) Fang, Y. Q.; Hanan, G. S. Rapid and Efficient Synthesis of
Functionalized Bipyridines. Synlett 2003, 852−854.
(35) Weiss, E. A.; Tauber, M. J.; Kelley, R. F.; Ahrens, M. J.; Ratner,
M. A.; Wasielewski, M. R. Conformationally Gated Switching Between
Superexchange and Hopping Within Oligo-p-Phenylene-Based Mo-
lecular Wires. J. Am. Chem. Soc. 2005, 127, 11842−11850.
(36) Tour, J. M. Conjugated Macromolecules of Precise Length and
Constitution. Organic Synthesis for the Construction of Nano-
architectures. Chem. Rev. 1996, 96, 537−553.
(57) Hankache, J.; Wenger, O. S. Microsecond Charge Recombina-
tion in a Linear Triarylamine-Ru(bpy)32+-Anthraquinone Triad. Chem.
Commun. 2011, 47, 10145−10147.
(58) Hensel, V.; Lutzow, K.; Jacob, J.; Gessler, K.; Saenger, W.;
(37) Walther, M. E.; Wenger, O. S. Tuning the Rates of Long-Range
Charge Transfer across Phenylene Wires. ChemPhysChem 2009, 10,
1203−1206.
(38) Natali, M.; Campagna, S.; Scandola, F. Photoinduced Electron
Transfer Across Molecular Bridges: Electron- and Hole-Transfer
Superexchange Pathways. Chem. Soc. Rev. 2014, 43, 4005−4018.
(39) Eng, M. P.; Albinsson, B. The Dependence of the Electronic
Coupling on Energy Gap and Bridge Conformation − Towards
Prediction of the Distance Dependence of Electron Transfer
Reactions. Chem. Phys. 2009, 357, 132−139.
Schluter, A. D. Repetitive Construction of Macrocyclic Oligopheny-
̈
lenes. Angew. Chem., Int. Ed. 1997, 36, 2654−2656.
(59) Hensel, V.; Schluter, A. D. A Biphenyl Construction Kit for
̈
Modular Chemistry. Liebigs Ann. 1997, 303−309.
(60) Hanss, D.; Wenger, O. S. Tunneling Barrier Effects on
Photoinduced Charge Transfer through Covalent Rigid Rod-Like
Bridges. Inorg. Chem. 2009, 48, 671−680.
(61) Lambert, C.; Noll, G.; Schmalzlin, E.; Meerholz, K.; Brauchle, C.
̈
̈
̈
Synthesis, (Non)Linear Optical and Redox Properties of a Donor-
Substituted Truxenone Derivative. Chem.Eur. J. 1998, 4, 2129−
2135.
(40) Miller, S. E.; Lukas, A. S.; Marsh, E.; Bushard, P.; Wasielewski,
M. R. Photoinduced Charge Separation Involving an Unusual Double
Electron Transfer Mechanism in a Donor-Bridge-Acceptor Molecule. J.
Am. Chem. Soc. 2000, 122, 7802−7810.
(62) Bonn, A. G.; Neuburger, M.; Wenger, O. S. Photoinduced
Electron Transfer in Rhenium(I)-Oligotriarylamine Molecules. Inorg.
Chem. 2014, 53, 11075−11085.
(41) Lambert, C.; Noll, G.; Schelter, J. Bridge-Mediated Hopping or
̌
(63) Vlcek, A. A.; Dodsworth, E. S.; Pietro, W. J.; Lever, A. B. P.
̈
Superexchange Electron-Transfer Processes in Bis(Triarylamine)
Systems. Nat. Mater. 2002, 1, 69−73.
Excited-State Redox Potentials of Ruthenium Diimine Complexes -
Correlations with Ground-State Redox Potentials and Ligand
Parameters. Inorg. Chem. 1995, 34, 1906−1913.
(42) Hanss, D.; Walther, M. E.; Wenger, O. S. Accelerated Hole
Transfer Across a Molecular Double Barrier. Chem. Commun. 2010,
46, 7034−7036.
(64) Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.;
Von Zelewsky, A. Ru(II) Polypyridine Complexes - Photophysics,
Photochemistry, Electrochemistry, and Chemi-Luminescence. Coord.
Chem. Rev. 1988, 84, 85−277.
(65) Hankache, J.; Niemi, M.; Lemmetyinen, H.; Wenger, O. S.
Photoinduced Electron Transfer in Linear Triarylamine-Photosensi-
(43) Kilsa, K.; Kajanus, J.; Macpherson, A. N.; Martensson, J.;
̊
̊
Albinsson, B. Bridge-Dependent Electron Transfer in Porphyrin-Based
Donor-Bridge-Acceptor Systems. J. Am. Chem. Soc. 2001, 123, 3069−
3080.
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