Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties

Yarnell, James E.; Davydenko, Iryna; Dorovatovskii, Pavel V.; Khrustalev, Victor N.; Timofeeva, Tatiana V.; Castellano, Felix N.; Marder, Seth R.; Risko, Chad; Barlow, Stephen

doi:10.1021/acs.jpcc.8b01003

Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties

Journal Article · Fri Feb 23 04:00:00 EST 2018 · Journal of Physical Chemistry. C

DOI:https://doi.org/10.1021/acs.jpcc.8b01003· OSTI ID:1633634

Yarnell, James E. ^[1]; Davydenko, Iryna ^[2]; Dorovatovskii, Pavel V. ^[3]; ^[4]; ^[5]; ^[6]; ^[2]; ^[7]; ^[2]

North Carolina State Univ., Raleigh, NC (United States); NC State University
Georgia Inst. of Technology, Atlanta, GA (United States)
National Research Centre, Moscow (Russian Federation). Kurchatov Institute
New Mexico Highlands Univ., Las Vegas, NM (United States); Peoples’ Friendship Univ. of Russia (RUDN Univ.), Moscow (Russian Federation)
New Mexico Highlands Univ., Las Vegas, NM (United States)
North Carolina State Univ., Raleigh, NC (United States)
Univ. of Kentucky, Lexington, KY (United States)

In this research, the synthesis and photophysical properties of a series of new chromophores featuring Pt(II) σ-bonded to perylenediimide (PDI) cores are reported. A Pt(PPh₃)₂X (X = Cl, Br) moiety was attached to PDI in either the ortho or the bay position (2- or 1-positions respectively) or a Pt(PPh₃)₂ subunit was used to bridge two bay positions (1- and 12-positions) forming a Pt(II) cyclometalate. Through a combination of steady-state and transient absorption and photoluminescence spectroscopy, the excited-state dynamics of these molecules were revealed, indicating that the Pt atom location on the PDI has a substantial impact on observed intersystem crossing (ISC) rates. The ISC time constants for the bay-substituted and cyclometalated PDIs are between 2.67 and 1.29 ns, respectively, determined by the singlet fluorescence decays from the initially populated singlet excited states. In the case of the ortho-substituted PDI, ISC to the triplet state occurs on the ultrafast time scale with a time constant of 345 fs, determined through ultrafast transient absorption spectroscopy. In all examples, the measured PDI-based fluorescence quantum yields quantitatively correlate with the measured ISC rates leaving little doubt that variation in the Pt(II) substitution position(s) markedly influence the resultant photophysics. Electronic structure calculations suggest differing amounts of metal-based contributions in the lowest excited states as a function of substitution position, supporting the trend of the observed ISC rates.

View Accepted Manuscript (DOE)

Research Organization:: North Carolina State Univ., Raleigh, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; Office of Naval Research (ONR); National Science Foundation (NSF); Air Force Office of Scientific Research (AFOSR)

Grant/Contract Number:: SC0011979

OSTI ID:: 1633634

Journal Information:: Journal of Physical Chemistry. C, Journal Name: Journal of Physical Chemistry. C Journal Issue: 25 Vol. 122; ISSN 1932-7447

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (98)

Perylene Derivatives with Large Two-Photon-Absorption Cross-Sections for Application in Optical Limiting and Upconversion Lasing Oliveira, S. L.; Corrêa, D. S.; Misoguti, L. Advanced Materials, Vol. 17, Issue 15 https://doi.org/10.1002/adma.200500533	journal	August 2005
Efficient Organic Heterojunction Photovoltaic Cells Based on Triplet Materials Shao, Y.; Yang, Y. Advanced Materials, Vol. 17, Issue 23 https://doi.org/10.1002/adma.200501297	journal	December 2005
Rylene and Related Diimides for Organic Electronics Zhan, Xiaowei; Facchetti, Antonio; Barlow, Stephen Advanced Materials, Vol. 23, Issue 2, p. 268-284 https://doi.org/10.1002/adma.201001402	journal	December 2010
New Organic Semiconductors with Imide/Amide-Containing Molecular Systems Liu, Zitong; Zhang, Guanxin; Cai, Zhengxu Advanced Materials, Vol. 26, Issue 40 https://doi.org/10.1002/adma.201305718	journal	March 2014
High-Mobility Air-Stable n-Type Semiconductors with Processing Versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides) Jones, Brooks A.; Ahrens, Michael J.; Yoon, Myung-Han Angewandte Chemie, Vol. 116, Issue 46 https://doi.org/10.1002/ange.200461324	journal	November 2004
The Rylene Colorant Family-Tailored Nanoemitters for Photonics Research and Applications Weil, Tanja; Vosch, Tom; Hofkens, Johan Angewandte Chemie International Edition, Vol. 49, Issue 48 https://doi.org/10.1002/anie.200902532	journal	October 2010
2-Triorgano-silyl, -germyl, -stannyl and -plumbyl derivatives of 1,3-diisopropyl-benzo-1,3,2-diazaborolidine and related compounds and their reactions with (η ² -C ₂ H ₄ )Pt(PPh ₃ ) ₂: Diazaborolidines bearing Group 14 substituents Habereder, Tassilo; Nöth, Heinrich Applied Organometallic Chemistry, Vol. 17, Issue 6-7 https://doi.org/10.1002/aoc.479	journal	May 2003
Über die reduktive Eliminierung des Biphenyl-Systems aus substituiertentrans-Diphenylbis(triphenylphosphan)platin(II)-Verbindungen Ertl, Josef; Debaerdemaeker, Tony; Brune, Hans Albert Chemische Berichte, Vol. 115, Issue 12 https://doi.org/10.1002/cber.19821151217	journal	December 1982
Dendronized Perylenetetracarboxdiimides with Peripheral Triphenylamines for Intramolecular Energy and Electron Transfer Qu, Jianqiang; Pschirer, Neil G.; Liu, Daojun Chemistry - A European Journal, Vol. 10, Issue 2 https://doi.org/10.1002/chem.200304994	journal	January 2004
Light-Harvesting Metallosupramolecular Squares Composed of Perylene Bisimide Walls and Fluorescent Antenna Dyes You, Chang-Cheng; Hippius, Catharina; Grüne, Matthias Chemistry - A European Journal, Vol. 12, Issue 28 https://doi.org/10.1002/chem.200600413	journal	September 2006
Exposing the Excited-State Equilibrium in an Ir ^III Bichromophore: A Combined Time Resolved Spectroscopy and Computational Study Yarnell, James E.; McCusker, Catherine E.; Leeds, Alexander J. European Journal of Inorganic Chemistry, Vol. 2016, Issue 12 https://doi.org/10.1002/ejic.201600194	journal	March 2016
Control of the Interactions in Multichromophores: Novel Concepts. Perylene Bis-imides as Components for Larger Functional Units Langhals, Heinz Helvetica Chimica Acta, Vol. 88, Issue 6 https://doi.org/10.1002/hlca.200590107	journal	June 2005
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
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 Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence Juris, A.; Balzani, V.; Barigelletti, F. Coordination Chemistry Reviews, Vol. 84 https://doi.org/10.1016/0010-8545(88)80032-8	journal	March 1988
Luminescent donor-acceptor platinum(ii) complexes Chan, Chin-Wing; Cheng, Luk-Ki; Che, Chi-Ming Coordination Chemistry Reviews, Vol. 132 https://doi.org/10.1016/0010-8545(94)80027-8	journal	May 1994
Platinum diimine complexes: towards a molecular photochemical device Hissler, Muriel; McGarrah, James E.; Connick, William B. Coordination Chemistry Reviews, Vol. 208, Issue 1 https://doi.org/10.1016/S0010-8545(00)00254-X	journal	October 2000
Luminescent platinum complexes: tuning and using the excited state Paw, Witold; Cummings, Scott D.; Adnan Mansour, M. Coordination Chemistry Reviews, Vol. 171 https://doi.org/10.1016/S0010-8545(98)90023-6	journal	April 1998
Crystal and molecular structure of cis-chloro-p-tolyl-bis(triethylphosphine)platinum(II) and of cis-chloro-perfluorophenyl-bis(triethylphosphine)platinum(II) Bresciani-Pahor, N.; Plazzotta, M.; Randaccio, L. Inorganica Chimica Acta, Vol. 31 https://doi.org/10.1016/S0020-1693(00)94995-8	journal	January 1978
Chiral platinum(II) complexes. Crystal and molecular structures of cis-[PtPhCl((R,R)-CHIRAPHOS)] and cis-[PtCl2((R,R)-CHIRAPHOS)] Johansson, Maria H.; Malmström, Torsten; Wendt, Ola F. Inorganica Chimica Acta, Vol. 316, Issue 1-2 https://doi.org/10.1016/S0020-1693(01)00396-6	journal	May 2001
Intramolecular radiationless transitions dominate exciton relaxation dynamics Jumper, Chanelle C.; Anna, Jessica M.; Stradomska, Anna Chemical Physics Letters, Vol. 599 https://doi.org/10.1016/j.cplett.2014.03.007	journal	April 2014
Perylene diimide based all small-molecule organic solar cells: Impact of branched-alkyl side chains on solubility, photophysics, self-assembly, and photovoltaic parameters Sun, Jon-Paul; Hendsbee, Arthur D.; Dobson, Alexander J. Organic Electronics, Vol. 35 https://doi.org/10.1016/j.orgel.2016.05.012	journal	August 2016
Bulk heterojunction organic photovoltaic devices based on low band gap small molecule BTD-TNP and perylene–anthracene diimide Sharma, G. D.; Balraju, P.; Mikroyannidis, John A. Solar Energy Materials and Solar Cells, Vol. 93, Issue 11 https://doi.org/10.1016/j.solmat.2009.08.003	journal	November 2009
Tetrahedral rigid core antenna chromophores bearing bay-substituted perylenediimides Myahkostupov, Mykhaylo; Castellano, Felix N. Tetrahedron, Vol. 71, Issue 51 https://doi.org/10.1016/j.tet.2015.10.083	journal	December 2015
Luminescent Mononuclear and Dinuclear Iridium(III) Cyclometalated Complexes Immobilized in a Polymeric Matrix as Solid-State Oxygen Sensors Di Marco, Gaetano; Lanza, Maurizio; Mamo, Antonino Analytical Chemistry, Vol. 70, Issue 23 https://doi.org/10.1021/ac980234p	journal	December 1998
Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials Würthner, Frank; Saha-Möller, Chantu R.; Fimmel, Benjamin Chemical Reviews, Vol. 116, Issue 3 https://doi.org/10.1021/acs.chemrev.5b00188	journal	August 2015
Transient Absorption Dynamics of Sterically Congested Cu(I) MLCT Excited States Garakyaraghi, Sofia; Danilov, Evgeny O.; McCusker, Catherine E. The Journal of Physical Chemistry A, Vol. 119, Issue 13 https://doi.org/10.1021/acs.jpca.5b00901	journal	March 2015
Access to Triplet Excited State in Core-Twisted Perylenediimide Nagarajan, Kalaivanan; Mallia, Ajith R.; Reddy, V. Sivaranjana The Journal of Physical Chemistry C, Vol. 120, Issue 16 https://doi.org/10.1021/acs.jpcc.6b00755	journal	April 2016
Comparison of the Optical and Electrochemical Properties of Bi(perylene diimide)s Linked through Ortho and Bay Positions Fan, Yeli; Ziabrev, Kostiantyn; Zhang, Siyuan ACS Omega, Vol. 2, Issue 2 https://doi.org/10.1021/acsomega.6b00537	journal	February 2017
Altering Molecular Photophysics by Merging Organic and Inorganic Chromophores Castellano, Felix N. Accounts of Chemical Research, Vol. 48, Issue 3 https://doi.org/10.1021/ar500385e	journal	February 2015
Singlet Fission Smith, Millicent B.; Michl, Josef Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr1002613	journal	November 2010
Electronic spectra and photophysics of platinum(II) complexes with .alpha.-diimine ligands. Mixed complexes with halide ligands Miskowski, Vincent M.; Houlding, Virginia H.; Che, Chi Ming Inorganic Chemistry, Vol. 32, Issue 11 https://doi.org/10.1021/ic00063a052	journal	May 1993
Luminescence characterizations of cyclometalated rhenium(I) carbonyl complexes Spellane, Peter; Watts, Richard J.; Vogler, Arnd Inorganic Chemistry, Vol. 32, Issue 24 https://doi.org/10.1021/ic00076a036	journal	November 1993
Facial tris cyclometalated rhodium(3+) and iridium(3+) complexes: their synthesis, structure, and optical spectroscopic properties Colombo, Mirco G.; Brunold, Thomas C.; Riedener, Toni Inorganic Chemistry, Vol. 33, Issue 3 https://doi.org/10.1021/ic00081a024	journal	February 1994
Cyclometalated complexes of ruthenium. 2. Spectral and electrochemical properties and x-ray structure of bis(2,2'-bipyridine)(4-nitro-2-(2-pyridyl)phenyl)ruthenium(II) Reveco, P.; Schmehl, R. H.; Cherry, W. R. Inorganic Chemistry, Vol. 24, Issue 24 https://doi.org/10.1021/ic00218a023	journal	November 1985
Electronic spectra and photophysics of platinum(II) complexes with .alpha.-diimine ligands. Solid-state effects. 1. Monomers and ligand .pi. dimers Miskowski, Vincent M.; Houlding, Virginia H. Inorganic Chemistry, Vol. 28, Issue 8 https://doi.org/10.1021/ic00307a021	journal	April 1989
Photophysics of Diimine Platinum(II) Bis-Acetylide Complexes Whittle, C. Ed; Weinstein, Julia A.; George, Michael W. Inorganic Chemistry, Vol. 40, Issue 16 https://doi.org/10.1021/ic0102182	journal	July 2001
Excited-State Absorption Properties of Platinum(II) Terpyridyl Acetylides Shikhova, Elena; Danilov, Evgeny O.; Kinayyigit, Solen Inorganic Chemistry, Vol. 46, Issue 8 https://doi.org/10.1021/ic0618652	journal	April 2007
Highly Fluorescent Platinum(II) Organometallic Complexes of Perylene and Perylene Monoimide, with Pt σ-Bonded Directly to the Perylene Core Lentijo, Sergio; Miguel, Jesús A.; Espinet, Pablo Inorganic Chemistry, Vol. 49, Issue 20 https://doi.org/10.1021/ic1003319	journal	October 2010
Bidirectional “Ping-Pong” Energy Transfer and 3000-Fold Lifetime Enhancement in a Re(I) Charge Transfer Complex Yarnell, James E.; Deaton, Joseph C.; McCusker, Catherine E. Inorganic Chemistry, Vol. 50, Issue 16 https://doi.org/10.1021/ic200974h	journal	August 2011
Ligand-Localized Triplet-State Photophysics in a Platinum(II) Terpyridyl Perylenediimideacetylide Prusakova, Valentina; McCusker, Catherine E.; Castellano, Felix N. Inorganic Chemistry, Vol. 51, Issue 15 https://doi.org/10.1021/ic301169t	journal	July 2012
Palladium Complexes of Perylene Diimides: Strong Fluorescence Despite Direct Attachment of Late Transition Metals to Organic Dyes Weissman, Haim; Shirman, Elijah; Ben-Moshe, Tal Inorganic Chemistry, Vol. 46, Issue 12 https://doi.org/10.1021/ic700539b	journal	June 2007
Photooxidation of Diimine Dithiolate Platinium(II) Complexes Induced by Charge Transfer to Diimine Excitation Zhang, Yin; Ley, Kevin D.; Schanze, Kirk S. Inorganic Chemistry, Vol. 35, Issue 24 https://doi.org/10.1021/ic960685x	journal	January 1996
Excited-State Self-Quenching Reactions of Square Planar Platinum(II) Diimine Complexes in Room-Temperature Fluid Solution Connick, William B.; Geiger, David; Eisenberg, Richard Inorganic Chemistry, Vol. 38, Issue 14 https://doi.org/10.1021/ic981387y	journal	July 1999
Platinum Diimine Bis(acetylide) Complexes: Synthesis, Characterization, and Luminescence Properties Hissler, Muriel; Connick, William B.; Geiger, David K. Inorganic Chemistry, Vol. 39, Issue 3 https://doi.org/10.1021/ic991250n	journal	February 2000
Lowest Electronic Excited States of Platinum(II) Diimine Complexes Connick, William B.; Miskowski, Vincent M.; Houlding, Virginia H. Inorganic Chemistry, Vol. 39, Issue 12 https://doi.org/10.1021/ic991369w	journal	May 2000
Application of the energy gap law to nonradiative, excited-state decay Caspar, Jonathan V.; Meyer, Thomas J. The Journal of Physical Chemistry, Vol. 87, Issue 6 https://doi.org/10.1021/j100229a010	journal	March 1983
Electrochemistry and spectroscopy of ortho-metalated complexes of iridium(III) and rhodium(III) Ohsawa, Y.; Sprouse, S.; King, K. A. The Journal of Physical Chemistry, Vol. 91, Issue 5 https://doi.org/10.1021/j100289a009	journal	February 1987
Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative Ford, William E.; Kamat, Prashant V. The Journal of Physical Chemistry, Vol. 91, Issue 25 https://doi.org/10.1021/j100309a012	journal	December 1987
Photoluminescence of platinum complex [PtII(4,7-diphenyl-1,10-phenanthroline)(CN)2] in solution Kunkely, Horst; Vogler, Arnd Journal of the American Chemical Society, Vol. 112, Issue 14 https://doi.org/10.1021/ja00170a029	journal	July 1990
Excited-state properties of a triply ortho-metalated iridium(III) complex King, K. A.; Spellane, P. J.; Watts, Richard J. Journal of the American Chemical Society, Vol. 107, Issue 5 https://doi.org/10.1021/ja00291a064	journal	March 1985
Photophysical effects of metal-carbon .sigma. bonds in ortho-metalated complexes of iridium(III) and rhodium(III) Sprouse, S.; King, K. A.; Spellane, P. J. Journal of the American Chemical Society, Vol. 106, Issue 22 https://doi.org/10.1021/ja00334a031	journal	October 1984
Application of the energy gap law to the decay of charge-transfer excited states Caspar, Jonathan V.; Kober, Edward M.; Sullivan, B. Patrick Journal of the American Chemical Society, Vol. 104, Issue 2 https://doi.org/10.1021/ja00366a051	journal	January 1982
Attaching Perylene Dyes to Polyfluorene: Three Simple, Efficient Methods for Facile Color Tuning of Light-Emitting Polymers Ego, Christophe; Marsitzky, Dirk; Becker, Stefan Journal of the American Chemical Society, Vol. 125, Issue 2 https://doi.org/10.1021/ja0205784	journal	January 2003
Ultrafast Energy-Electron Transfer Cascade in a Multichromophoric Light-Harvesting Molecular Square Sautter, Armin; Kaletaş, Başak Kükrer; Schmid, Dietmar G. Journal of the American Chemical Society, Vol. 127, Issue 18 https://doi.org/10.1021/ja0448216	journal	May 2005
Combining Light-Harvesting and Charge Separation in a Self-Assembled Artificial Photosynthetic System Based on Perylenediimide Chromophores Rybtchinski, Boris; Sinks, Louise E.; Wasielewski, Michael R. Journal of the American Chemical Society, Vol. 126, Issue 39 https://doi.org/10.1021/ja0460514	journal	October 2004
Ultrafast Aggregate-to-Aggregate Energy Transfer within Self-assembled Light-Harvesting Columns of Zinc Phthalocyanine Tetrakis(Perylenediimide) Li, Xiyou; Sinks, Louise E.; Rybtchinski, Boris Journal of the American Chemical Society, Vol. 126, Issue 35 https://doi.org/10.1021/ja047176b	journal	September 2004
A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar Cells Zhan, Xiaowei; Tan, Zhan'ao; Domercq, Benoit Journal of the American Chemical Society, Vol. 129, Issue 23, p. 7246-7247 https://doi.org/10.1021/ja071760d	journal	June 2007
Supermolecular-Chromophore-Sensitized Near-Infrared-to-Visible Photon Upconversion Singh-Rachford, Tanya N.; Nayak, Animesh; Muro-Small, Maria L. Journal of the American Chemical Society, Vol. 132, Issue 40 https://doi.org/10.1021/ja105510k	journal	October 2010
Accessing the Triplet Excited State in Perylenediimides Rachford, Aaron A.; Goeb, Sébastien; Castellano, Felix N. Journal of the American Chemical Society, Vol. 130, Issue 9 https://doi.org/10.1021/ja800333y	journal	March 2008
Tuning the Excited-State Properties of Platinum(II) Diimine Dithiolate Complexes Cummings, Scott D.; Eisenberg, Richard Journal of the American Chemical Society, Vol. 118, Issue 8 https://doi.org/10.1021/ja951345y	journal	January 1996
Photooxidation of Platinum(II) Diimine Dithiolates Connick, William B.; Gray, Harry B. Journal of the American Chemical Society, Vol. 119, Issue 48 https://doi.org/10.1021/ja9723803	journal	December 1997
Facile Incorporation of Pd(PPh ₃ ) ₂ Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions Davydenko, Iryna; Barlow, Stephen; Sharma, Rajesh Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b06361	journal	August 2016
Charge Localization after Ultrafast Photoexcitation of a Rigid Perylene Perylenediimide Dyad Visualized by Transient Stark Effect Koch, Marius; Myahkostupov, Mykhaylo; Oblinsky, Daniel G. Journal of the American Chemical Society, Vol. 139, Issue 15 https://doi.org/10.1021/jacs.7b01630	journal	April 2017
Synthesis of a Bis(pyridyl)-Substituted Perylene Diimide Ligand and Incorporation into a Supramolecular Rhomboid and Rectangle via Coordination Driven Self-Assembly Addicott, Chris; Oesterling, Ingo; Yamamoto, Takuya The Journal of Organic Chemistry, Vol. 70, Issue 3 https://doi.org/10.1021/jo048239b	journal	February 2005
Energy, Charge, and Spin Transport in Molecules and Self-Assembled Nanostructures Inspired by Photosynthesis Wasielewski, Michael R. The Journal of Organic Chemistry, Vol. 71, Issue 14 https://doi.org/10.1021/jo060225d	journal	July 2006
Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics Huang, Chun; Barlow, Stephen; Marder, Seth R. The Journal of Organic Chemistry, Vol. 76, Issue 8 https://doi.org/10.1021/jo2001963	journal	April 2011
Structural Refinement of Ladder-Type Perylenediimide Dimers: A Classical Tale of Conformational Dynamics Myahkostupov, Mykhaylo; Prusakova, Valentina; Oblinsky, Daniel G. The Journal of Organic Chemistry, Vol. 78, Issue 17 https://doi.org/10.1021/jo401348w	journal	August 2013
Evolution of the Triplet Excited State in Pt ^II Perylenediimides Danilov, Evgeny O.; Rachford, Aaron A.; Goeb, Sébastien The Journal of Physical Chemistry A, Vol. 113, Issue 19 https://doi.org/10.1021/jp9012762	journal	May 2009
Vibrational Dynamics of a Perylene–Perylenediimide Donor–Acceptor Dyad Probed with Femtosecond Stimulated Raman Spectroscopy Brown, Kristen E.; Veldkamp, Brad S.; Co, Dick T. The Journal of Physical Chemistry Letters, Vol. 3, Issue 17 https://doi.org/10.1021/jz301107c	journal	August 2012
Donor−Acceptor Poly(thiophene- block -perylene diimide) Copolymers: Synthesis and Solar Cell Fabrication Zhang, Qingling; Cirpan, Ali; Russell, Thomas P. Macromolecules, Vol. 42, Issue 4 https://doi.org/10.1021/ma801504e	journal	February 2009
Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides Teraoka, Takuro; Hiroto, Satoru; Shinokubo, Hiroshi Organic Letters, Vol. 13, Issue 10 https://doi.org/10.1021/ol2004534	journal	May 2011
Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding Ito, Satoru; Hiroto, Satoru; Shinokubo, Hiroshi Organic Letters, Vol. 15, Issue 12 https://doi.org/10.1021/ol401316q	journal	June 2013
A novel reactivity in the reaction of cycloheptatetraene with Pt(PPh3)3 Winchester, William R.; Gawron, Marian.; Palenik, Gus J. Organometallics, Vol. 4, Issue 10 https://doi.org/10.1021/om00129a037	journal	October 1985
Formation of Phenylene Oligomers Using Platinum−Phosphine Complexes Simhai, Nira; Iverson, Carl N.; Edelbach, Brian L. Organometallics, Vol. 20, Issue 13 https://doi.org/10.1021/om010111m	journal	May 2001
Synthesis and Structure of Platinum Bis(phospholane) Complexes Pt(diphos*)(R)(X), Catalyst Precursors for Asymmetric Phosphine Alkylation Guino-o, Marites A.; Zureick, Andrew H.; Blank, Natalia F. Organometallics, Vol. 31, Issue 19 https://doi.org/10.1021/om300704e	journal	September 2012
Non-fullerene acceptors for organic solar cells Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui Nature Reviews Materials, Vol. 3, Issue 3 https://doi.org/10.1038/natrevmats.2018.3	journal	February 2018
Metallosupramolecular squares: from structure to function Würthner, Frank; You, Chang-Cheng; Saha-Möller, Chantu R. Chem. Soc. Rev., Vol. 33, Issue 3 https://doi.org/10.1039/B300512G	journal	January 2004
Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Würthner, Frank Chem. Commun., Issue 14 https://doi.org/10.1039/B401630K	journal	January 2004
Platinum–acetylide polymer based solar cells: involvement of the triplet state for energy conversion Guo, Fengqi; Kim, Young-Gi; Reynolds, John R. Chem. Commun., Issue 17 https://doi.org/10.1039/B516086C	journal	January 2006
Perylenediimides as non-fullerene acceptors in bulk-heterojunction solar cells (BHJSCs) Fernández-Lázaro, Fernando; Zink-Lorre, Nathalie; Sastre-Santos, Ángela Journal of Materials Chemistry A, Vol. 4, Issue 24 https://doi.org/10.1039/C6TA02045C	journal	January 2016
Effects of meso -M(PPh ₃ ) ₂ Cl (M = Pd, Ni) substituents on the linear and third-order nonlinear optical properties of chalcogenopyrylium-terminated heptamethines in solution and solid states Davydenko, Iryna; Benis, Sepehr; Shiring, Stephen B. Journal of Materials Chemistry C, Vol. 6, Issue 14 https://doi.org/10.1039/C7TC05050J	journal	January 2018
Generation of (η2-benzyne)bis(triphenylphosphine)platinum(>0>): orthometallation of the Pt(PPh3)2 complexes of benzyne (C6H4 ) and cyclohexyne (C6H8) Bennett, Martin A.; Dirnberger, Thomas; Hockless, David C. R. Journal of the Chemical Society, Dalton Transactions, Issue 2 https://doi.org/10.1039/a707089f	journal	January 1998
Synthesis and characterisation of new platinum–acetylide complexes containing diimine ligands Adams, Christopher J.; James, Stuart L.; Liu, Xiaoming Journal of the Chemical Society, Dalton Transactions, Issue 1 https://doi.org/10.1039/a907028a	journal	January 2000
Photo-induced charge transfer and nonlinear absorption in dyads composed of a two-photon-absorbing donor and a perylene diimide acceptor Huang, Chun; Sartin, Matthew M.; Siegel, Nisan Journal of Materials Chemistry, Vol. 21, Issue 40 https://doi.org/10.1039/c1jm12566d	journal	January 2011
Transition metal complexes meet the rylenes Castellano, Felix N. Dalton Transactions, Vol. 41, Issue 28 https://doi.org/10.1039/c2dt30765k	journal	January 2012
Near-IR phosphorescent metalloporphyrin as a photochemical upconversion sensitizer Deng, Fan; Sommer, Jonathan R.; Myahkostupov, Mykhaylo Chemical Communications, Vol. 49, Issue 67 https://doi.org/10.1039/c3cc44479a	journal	January 2013
Photophysical properties of polypyridyl carbonyl complexes of rhenium(I) Worl, Laura A.; Duesing, Rich; Chen, Pingyun Journal of the Chemical Society, Dalton Transactions, Issue S https://doi.org/10.1039/dt9910000849	journal	January 1991
Natural transition orbitals Martin, Richard L. The Journal of Chemical Physics, Vol. 118, Issue 11 https://doi.org/10.1063/1.1558471	journal	March 2003
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1 https://doi.org/10.1063/1.448799	journal	January 1985
Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi Wadt, Willard R.; Hay, P. Jeffrey The Journal of Chemical Physics, Vol. 82, Issue 1 https://doi.org/10.1063/1.448800	journal	January 1985
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310 https://doi.org/10.1063/1.448975	journal	January 1985
Quantum Yields for the Photosensitized Formation of the Lowest Electronically Excited Singlet State of Molecular Oxygen in Solution Wilkinson, Francis; Helman, W. Phillip; Ross, Alberta B. Journal of Physical and Chemical Reference Data, Vol. 22, Issue 1 https://doi.org/10.1063/1.555934	journal	January 1993
cis-(E)-Bis(7-methyl-1-naphthyl)bis(triphenylphosphine)platinum(II) Debaerdemaeker, T.; Berhalter, K.; Weisemann, C. Acta Crystallographica Section C Crystal Structure Communications, Vol. 43, Issue 7 https://doi.org/10.1107/S0108270187092254	journal	July 1987
Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics Schmidt-Mende, L. Science, Vol. 293, Issue 5532 https://doi.org/10.1126/science.293.5532.1119	journal	August 2001
cis -Bis(2 -methoxyphenyl)bis (triphenylphosphan)platin(II) Synthese, Kristall- und Molekülstruktur und thermisches Verhalten/cis-Bis(2-methoxyphenyl)bis(triphenylphosphane)platinum(II) Synthesis, Crystal and Molecular Structure and Thermal Stability Debaerdemaeker, Tony; Klein, Heinz-Peter; Wiege, Manfred Zeitschrift für Naturforschung B, Vol. 36, Issue 8 https://doi.org/10.1515/znb-1981-0813	journal	August 1981
Versuche zur Synthese 2.2′-disubstituierter cis-Bis(phenyl)bis(triphenylphosphan)platin(II)-Verbindungen und Kristallstruktur des cis-Bis(2-nitrophenyl)bis(triphenylphosphan)platin(II) / On the Formation of 2,2′-Disubstituted cis-Bis-(phenyl)bis(triphenylphosphane)platinum(II) Compounds and Crystal Structure Determination of cis-Bis(2-nitrophenyl)bis(triphenylphosphane)platinum(II) Brune, Hans-Albert; Wiege, Manfred; Debaerdemaeker, Tony Zeitschrift für Naturforschung B, Vol. 39, Issue 3 https://doi.org/10.1515/znb-1984-0315	journal	March 1984

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