Triphenylene‐Derived Electron Acceptors and Donors on Ag(111): Formation of Intermolecular Charge‐Transfer Complexes with Common Unoccupied Molecular States

Müller, Kathrin; Schmidt, Nico; Link, Stefan; Riedel, René; Bock, Julian; Malone, Walter; Lasri, Karima; Kara, Abdelkader; Starke, Ulrich; Kivala, Milan; Stöhr, Meike

doi:10.1002/smll.201901741

Title: Triphenylene‐Derived Electron Acceptors and Donors on Ag(111): Formation of Intermolecular Charge‐Transfer Complexes with Common Unoccupied Molecular States

Journal Article · 02 July 2019 · Small

DOI: https://doi.org/10.1002/smll.201901741 · OSTI ID:1671139

^[1]; Schmidt, Nico ^[2]; Link, Stefan ^[3]; Riedel, René ^[4]; Bock, Julian ^[5]; Malone, Walter ^[6]; Lasri, Karima ^[6]; Kara, Abdelkader ^[6]; Starke, Ulrich ^[3]; Kivala, Milan ^[5]; Stöhr, Meike ^[2]

Zernike Institute for Advanced Materials University of Groningen Nijenborgh 4 9747 AG Groningen Netherlands, Max Planck Institute for Solid State Research Heisenbergstrasse 1 D‐70569 Stuttgart Germany
Zernike Institute for Advanced Materials University of Groningen Nijenborgh 4 9747 AG Groningen Netherlands
Max Planck Institute for Solid State Research Heisenbergstrasse 1 D‐70569 Stuttgart Germany
Department of Chemistry and Pharmacy University of Erlangen‐Nürnberg Nikolaus‐Fiebiger‐Strasse 10 D‐91058 Erlangen Germany
Organisch‐Chemisches Institut &, Centre for Advanced Materials Ruprecht‐Karls‐Universität Heidelberg Im Neuenheimer Feld 270 &, 225 69120 Heidelberg Germany
Department of Physics University of Central Florida Orlando FL 32816 USA

Abstract Over the past years, ultrathin films consisting of electron donating and accepting molecules have attracted increasing attention due to their potential usage in optoelectronic devices. Key parameters for understanding and tuning their performance are intermolecular and molecule–substrate interactions. Here, the formation of a monolayer thick blend of triphenylene‐based organic donor and acceptor molecules from 2,3,6,7,10,11‐hexamethoxytriphenylene (HAT) and 1,4,5,8,9,12‐hexaazatriphenylenehexacarbonitrile (HATCN), respectively, on a silver (111) surface is reported. Scanning tunneling microscopy and spectroscopy, valence and core level photoelectron spectroscopy, as well as low‐energy electron diffraction measurements are used, complemented by density functional theory calculations, to investigate both the electronic and structural properties of the homomolecular as well as the intermixed layers. The donor molecules are weakly interacting with the Ag(111) surface, while the acceptor molecules show a strong interaction with the substrate leading to charge transfer and substantial buckling of the top silver layer and of the adsorbates. Upon mixing acceptor and donor molecules, strong hybridization occurs between the two different molecules leading to the emergence of a common unoccupied molecular orbital located at both the donor and acceptor molecules. The donor acceptor blend studied here is, therefore, a compelling candidate for organic electronics based on self‐assembled charge‐transfer complexes.

View Journal Article

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: DE‐FG02‐11ER16243

OSTI ID:: 1671139

Alternate ID(s):: OSTI ID: 1671140

Journal Information:: Small, Journal Name: Small Vol. 15 Journal Issue: 33; ISSN 1613-6810

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (75)

Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Understanding Energy-Level Alignment in Donor–Acceptor/Metal Interfaces from Core-Level Shifts El-Sayed, Afaf; Borghetti, Patrizia; Goiri, Elizabeth ACS Nano, Vol. 7, Issue 8 https://doi.org/10.1021/nn4020888	journal	July 2013
Molecule-based monochromatic and polychromatic OLEDs with wet-process feasibility Jou, Jwo-Huei; Sahoo, Snehasis; Dubey, Deepak Kumar Journal of Materials Chemistry C, Vol. 6, Issue 43 https://doi.org/10.1039/C8TC04203A	journal	January 2018
Organic Thin-Film Transistors for Chemical and Biological Sensing Lin, Peng; Yan, Feng Advanced Materials, Vol. 24, Issue 1 https://doi.org/10.1002/adma.201103334	journal	November 2011
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Hydrogen-Bonding Fingerprints in Electronic States of Two-Dimensional Supramolecular Assemblies Gonzalez-Lakunza, Nora; CaÃ±as-Ventura, Marta E.; Ruffieux, Pascal ChemPhysChem, Vol. 10, Issue 17 https://doi.org/10.1002/cphc.200900722	journal	December 2009
Orbital-Resolved Partial Charge Transfer from the Methoxy Groups of Substituted Pyrenes in Complexes with Tetracyanoquinodimethane—A NEXAFS Study Medjanik, Katerina; Chercka, Dennis; Nagel, Peter Journal of the American Chemical Society, Vol. 134, Issue 10 https://doi.org/10.1021/ja2100802	journal	February 2012
Organic Donor–Acceptor Complexes as Novel Organic Semiconductors Zhang, Jing; Xu, Wei; Sheng, Peng Accounts of Chemical Research, Vol. 50, Issue 7 https://doi.org/10.1021/acs.accounts.7b00124	journal	June 2017
Charge Transport Properties in Discotic Liquid Crystals: A Quantum-Chemical Insight into Structure−Property Relationships Lemaur, Vincent; da Silva Filho, Demetrio A.; Coropceanu, Veaceslav Journal of the American Chemical Society, Vol. 126, Issue 10 https://doi.org/10.1021/ja0390956	journal	March 2004
Cyano-Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule-Substrate Interactions Müller , Kathrin; Moreno-López, Juan Carlos; Gottardi, Stefano Chemistry - A European Journal, Vol. 22, Issue 2 https://doi.org/10.1002/chem.201503205	journal	December 2015
Self-Assembly of Bicomponent Molecular Monolayers: Adsorption Height Changes and Their Consequences Goiri, E.; Matena, M.; El-Sayed, A. Physical Review Letters, Vol. 112, Issue 11 https://doi.org/10.1103/PhysRevLett.112.117602	journal	March 2014
Charge transfer in the novel donor–acceptor complexes tetra- and hexamethoxypyrene with tetracyanoquinodimethane studied by HAXPES Medjanik, K.; Gloskovskii, A.; Kutnyakhov, D. Journal of Electron Spectroscopy and Related Phenomena, Vol. 185, Issue 3-4 https://doi.org/10.1016/j.elspec.2012.02.002	journal	April 2012
Überoxidation als Schlüsselschritt im Mechanismus der MoCl ₅ - vermittelten dehydrierenden Arenkupplung Schubert, Moritz; Franzmann, Peter; Wünsche von Leupoldt, Anica Angewandte Chemie, Vol. 128, Issue 3 https://doi.org/10.1002/ange.201508035	journal	October 2015
Effect of van der Waals Interactions on the Adsorption of Olympicene Radical on Cu(111): Characteristics of Weak Physisorption versus Strong Chemisorption Yildirim, Handan; Kara, Abdelkader The Journal of Physical Chemistry C, Vol. 117, Issue 6 https://doi.org/10.1021/jp311361e	journal	February 2013
Photofunctional nanomaterials composed of multiporphyrins and carbon-based π-electron acceptors Fukuzumi, Shunichi; Kojima, Takahiko Journal of Materials Chemistry, Vol. 18, Issue 13 https://doi.org/10.1039/b717958h	journal	January 2008
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
Chemical accuracy for the van der Waals density functional Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Journal of Physics: Condensed Matter, Vol. 22, Issue 2 https://doi.org/10.1088/0953-8984/22/2/022201	journal	December 2009
A High Yield Easy Method for the Preparation of Alkoxy-Substituted Triphenylenes Naarmann, Herbert; Hanack, Michael; Mattmer, Robert Synthesis, Vol. 1994, Issue 05 https://doi.org/10.1055/s-1994-25505	journal	January 1994
Accurate Band Gaps for Semiconductors from Density Functional Theory Xiao, Hai; Tahir-Kheli, Jamil; Goddard, William A. The Journal of Physical Chemistry Letters, Vol. 2, Issue 3 https://doi.org/10.1021/jz101565j	journal	January 2011
Understanding Charge Transfer in Donor–Acceptor/Metal Systems: A Combined Theoretical and Experimental Study Cabellos, J. L.; Mowbray, D. J.; Goiri, E. The Journal of Physical Chemistry C, Vol. 116, Issue 34 https://doi.org/10.1021/jp3004213	journal	August 2012
Understanding band gaps of solids in generalized Kohn–Sham theory Perdew, John P.; Yang, Weitao; Burke, Kieron Proceedings of the National Academy of Sciences, Vol. 114, Issue 11 https://doi.org/10.1073/pnas.1621352114	journal	March 2017
Resolution of the Band Gap Prediction Problem for Materials Design Crowley, Jason M.; Tahir-Kheli, Jamil; Goddard, William A. The Journal of Physical Chemistry Letters, Vol. 7, Issue 7 https://doi.org/10.1021/acs.jpclett.5b02870	journal	March 2016
Noncovalent Synthesis: Using Physical-Organic Chemistry To Make Aggregates Whitesides, George M.; Simanek, Eric E.; Mathias, John P. Accounts of Chemical Research, Vol. 28, Issue 1 https://doi.org/10.1021/ar00049a006	journal	January 1995
Organic Field-Effect Transistors Horowitz, Gilles Advanced Materials, Vol. 10, Issue 5 https://doi.org/10.1002/(SICI)1521-4095(199803)10:5<365::AID-ADMA365>3.0.CO;2-U	journal	March 1998
Organic-Inorganic Hybrid Materials as Semiconducting Channels in Thin-Film Field-Effect Transistors Kagan, C. R.; Mitzi, D. B.; Dimitrakopoulos, C. D. Science, Vol. 286, Issue 5441, p. 945-947 https://doi.org/10.1126/science.286.5441.945	journal	October 1999
Synthesis, mesomorphism and electronic properties of nonaflate and cyano-substituted pentyloxy and 3-methylbutyloxy triphenylenes Mahoney, Stuart J.; Ahmida, Mohamed M.; Kayal, Himadri Journal of Materials Chemistry, Vol. 19, Issue 48 https://doi.org/10.1039/b914290h	journal	January 2009
Ab initiomolecular dynamics for liquid metals Kresse, G.; Hafner, J. Physical Review B, Vol. 47, Issue 1, p. 558-561 https://doi.org/10.1103/PhysRevB.47.558	journal	January 1993
Balancing Intermolecular and Molecule-Substrate Interactions in Supramolecular Assemblies de Oteyza, Dimas G.; Silanes, Iñaki; Ruiz-Osés, Miguel Advanced Functional Materials, Vol. 19, Issue 2 https://doi.org/10.1002/adfm.200801453	journal	January 2009
Trends in Adsorption Characteristics of Benzene on Transition Metal Surfaces: Role of Surface Chemistry and van der Waals Interactions Yildirim, Handan; Greber, Thomas; Kara, Abdelkader The Journal of Physical Chemistry C, Vol. 117, Issue 40 https://doi.org/10.1021/jp404487z	journal	September 2013
Adsorption of thiophene on transition metal surfaces with the inclusion of van der Waals effects Malone, Walter; Matos, Jeronimo; Kara, Abdelkader Surface Science, Vol. 669 https://doi.org/10.1016/j.susc.2017.11.013	journal	March 2018
Tuning hole-injection barriers at organic/metal interfaces exploiting the orientation of a molecular acceptor interlayer Niederhausen, J.; Amsalem, P.; Frisch, J. Physical Review B, Vol. 84, Issue 16 https://doi.org/10.1103/PhysRevB.84.165302	journal	October 2011
The role of energy level matching in organic solar cells—Hexaazatriphenylene hexacarbonitrile as transparent electron transport material Falkenberg, Christiane; Olthof, Selina; Rieger, Ralph Solar Energy Materials and Solar Cells, Vol. 95, Issue 3 https://doi.org/10.1016/j.solmat.2010.11.024	journal	March 2011
Tunable Two-Dimensional Binary Molecular Networks Huang, Yu Li; Chen, Wei; Li, Hui Small, Vol. 6, Issue 1 https://doi.org/10.1002/smll.200901291	journal	January 2010
Solid-State Reactions in Binary Molecular Assemblies of F ₁₆ CuPc and Pentacene Wakayama, Yutaka; de Oteyza, Dimas G.; Garcia-Lastra, Juan M. ACS Nano, Vol. 5, Issue 1 https://doi.org/10.1021/nn102887x	journal	December 2010
Role of Long-Range Interactions for the Structure and Energetics of Olympicene Radical Adsorbed on Au(111) and Pt(111) Surfaces Yildirim, Handan; Matos, Jeronimo; Kara, Abdelkader The Journal of Physical Chemistry C, Vol. 119, Issue 45 https://doi.org/10.1021/acs.jpcc.5b08191	journal	November 2015
Trimodular Engineering of Linear Supramolecular Miniatures on Ag(111) Surfaces Controlled by Complementary Triple Hydrogen Bonds Llanes-Pallas, Anna; Matena, Manfred; Jung, Thomas Angewandte Chemie International Edition, Vol. 47, Issue 40 https://doi.org/10.1002/anie.200802325	journal	September 2008
Cyano-Functionalized Triarylamines on Au(111): Competing Intermolecular versus Molecule/Substrate Interactions Gottardi, Stefano; Müller, Kathrin; Moreno-López, Juan Carlos Advanced Materials Interfaces, Vol. 1, Issue 1 https://doi.org/10.1002/admi.201300025	journal	November 2013
Spectroscopic Fingerprints of Work-Function-Controlled Phthalocyanine Charging on Metal Surfaces Borghetti, Patrizia; El-Sayed, Afaf; Goiri, Elizabeth ACS Nano, Vol. 8, Issue 12 https://doi.org/10.1021/nn5060333	journal	November 2014
Energy Level Realignment in Weakly Interacting Donor–Acceptor Binary Molecular Networks Zhong, Jian-Qiang; Qin, Xinming; Zhang, Jia-Lin ACS Nano, Vol. 8, Issue 2 https://doi.org/10.1021/nn406050e	journal	January 2014
Formation of an intermolecular charge-transfer compound in UHV codeposited tetramethoxypyrene and tetracyanoquinodimethane Medjanik, K.; Perkert, S.; Naghavi, S. Physical Review B, Vol. 82, Issue 24 https://doi.org/10.1103/PhysRevB.82.245419	journal	December 2010
Growth of Dihydrotetraazapentacene Layers on Cu(110) Thomas, Anthony; Malone, Walter; Leoni, Thomas The Journal of Physical Chemistry C, Vol. 122, Issue 20 https://doi.org/10.1021/acs.jpcc.8b01336	journal	April 2018
Binary supramolecular networks of bridged triphenylamines with different substituents and identical scaffolds Steiner, Christian; Yang, Zechao; Gliemann, Bettina D. Chemical Communications, Vol. 54, Issue 82 https://doi.org/10.1039/C8CC04410D	journal	January 2018
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Formation of Dispersive Hybrid Bands at an Organic-Metal Interface Gonzalez-Lakunza, N.; Fernández-Torrente, I.; Franke, K. J. Physical Review Letters, Vol. 100, Issue 15 https://doi.org/10.1103/PhysRevLett.100.156805	journal	April 2008
Dipolar C[triple-bond]N...C[triple-bond]N interactions in organic crystal structures: database analysis and calculation of interaction energies Wood, Peter A.; Borwick, Simon J.; Watkin, David J. Acta Crystallographica Section B Structural Science, Vol. 64, Issue 3 https://doi.org/10.1107/S0108768108010239	journal	May 2008
Electronic structure of large disc-type donors and acceptors Medjanik, K.; Kutnyakhov, D.; Nepijko, S. A. Physical Chemistry Chemical Physics, Vol. 12, Issue 26 https://doi.org/10.1039/b926999a	journal	January 2010
Electronic, structural and chemical effects of charge-transfer at organic/inorganic interfaces Otero, R.; Vázquez de Parga, A. L.; Gallego, J. M. Surface Science Reports, Vol. 72, Issue 3 https://doi.org/10.1016/j.surfrep.2017.03.001	journal	July 2017
Controlling molecular deposition and layer structure with supramolecular surface assemblies Theobald, James A.; Oxtoby, Neil S.; Phillips, Michael A. Nature, Vol. 424, Issue 6952 https://doi.org/10.1038/nature01915	journal	August 2003
Supramolecular Environment-Dependent Electronic Properties of Metal–Organic Interfaces. El-Sayed, Afaf; Mowbray, Duncan J.; García-Lastra, Juan M. The Journal of Physical Chemistry C, Vol. 116, Issue 7 https://doi.org/10.1021/jp211749g	journal	February 2012
Electron transfer in a new highly conducting donor-acceptor complex Ferraris, John.; Cowan, D. O.; Walatka, V. Journal of the American Chemical Society, Vol. 95, Issue 3 https://doi.org/10.1021/ja00784a066	journal	February 1973
Insight into the Effect of Long Range Interactions for the Adsorption of Benzene on Transition Metal (110) Surfaces Matos, Jeronimo; Yildirim, Handan; Kara, Abdelkader The Journal of Physical Chemistry C, Vol. 119, Issue 4 https://doi.org/10.1021/jp511268s	journal	January 2015
Improving charge injection in organic thin-film transistors with thiol-based self-assembled monolayers Marmont, Patrick; Battaglini, Nicolas; Lang, Philippe Organic Electronics, Vol. 9, Issue 4 https://doi.org/10.1016/j.orgel.2008.01.004	journal	August 2008
Energy-Level Alignment at Organic/Metal and Organic/Organic Interfaces Braun, Slawomir; Salaneck, William R.; Fahlman, Mats Advanced Materials, Vol. 21, Issue 14-15, p. 1450-1472 https://doi.org/10.1002/adma.200802893	journal	April 2009
Customized Electronic Coupling in Self-Assembled DonorâAcceptor Nanostructures de Oteyza, Dimas G.; GarcÃa-Lastra, Juan M.; Corso, Martina Advanced Functional Materials, Vol. 19, Issue 22 https://doi.org/10.1002/adfm.200901374	journal	November 2009
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
White organic light-emitting diodes with fluorescent tube efficiency Reineke, Sebastian; Lindner, Frank; Schwartz, Gregor Nature, Vol. 459, Issue 7244 https://doi.org/10.1038/nature08003	journal	May 2009
Porphyrinoids for Chemical Sensor Applications Paolesse, Roberto; Nardis, Sara; Monti, Donato Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00361	journal	October 2016
2D Supramolecular Self-Assembly of Binary Organic Monolayers Barrena, Esther; de Oteyza, Dimas G.; Dosch, Helmut ChemPhysChem, Vol. 8, Issue 13 https://doi.org/10.1002/cphc.200700494	journal	September 2007
Multi-Component Organic Layers on Metal Substrates Goiri, Elizabeth; Borghetti, Patrizia; El-Sayed, Afaf Advanced Materials, Vol. 28, Issue 7 https://doi.org/10.1002/adma.201503570	journal	December 2015
Asymmetric Response toward Molecular Fluorination in Binary Copper–Phthalocyanine/Pentacene Assemblies de Oteyza, D. G.; Garcia-Lastra, J. M.; Goiri, E. The Journal of Physical Chemistry C, Vol. 118, Issue 32 https://doi.org/10.1021/jp506151j	journal	July 2014
Tuning the Work Function of Graphene-on-Quartz with a High Weight Molecular Acceptor Christodoulou, C.; Giannakopoulos, A.; Nardi, M. V. The Journal of Physical Chemistry C, Vol. 118, Issue 9 https://doi.org/10.1021/jp4122408	journal	February 2014
Bicomponent Supramolecular Architectures at the Vacuum–Solid Interface Bouju, Xavier; Mattioli, Cristina; Franc, Grégory Chemical Reviews, Vol. 117, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00389	journal	January 2017
Trimodular Engineering of Linear Supramolecular Miniatures on Ag(111) Surfaces Controlled by Complementary Triple Hydrogen Bonds Llanes-Pallas, Anna; Matena, Manfred; Jung, Thomas Angewandte Chemie, Vol. 120, Issue 40 https://doi.org/10.1002/ange.200802325	journal	September 2008
Complementary C ₃ -Symmetric Donor−Acceptor Components: Cocrystal Structure and Control of Mesophase Stability Park, Lee Y.; Hamilton, Darren G.; McGehee, Edward A. Journal of the American Chemical Society, Vol. 125, Issue 35 https://doi.org/10.1021/ja036540o	journal	September 2003
Molecular-Level Realignment in Donor–Acceptor Bilayer Blends on Metals Borghetti, P.; de Oteyza, D. G.; Rogero, C. The Journal of Physical Chemistry C, Vol. 120, Issue 11 https://doi.org/10.1021/acs.jpcc.5b11373	journal	March 2016
Two-dimensional molecular porous networks constructed by surface assembling Liang, Hailin; He, Yang; Ye, Yingchun Coordination Chemistry Reviews, Vol. 253, Issue 23-24 https://doi.org/10.1016/j.ccr.2009.07.028	journal	December 2009
Over-Oxidation as the Key Step in the Mechanism of the MoCl 5 -Mediated Dehydrogenative Coupling of Arenes Schubert, Moritz; Franzmann, Peter; Wünsche von Leupoldt, Anica Angewandte Chemie International Edition, Vol. 55, Issue 3 https://doi.org/10.1002/anie.201508035	journal	October 2015
1D and 3D surface-assisted self-organization Koepf, Matthieu; Chérioux, Frédéric; Wytko, Jennifer A. Coordination Chemistry Reviews, Vol. 256, Issue 23-24 https://doi.org/10.1016/j.ccr.2012.05.039	journal	December 2012
“Soft” Metallic Contact to Isolated C ₆₀ Molecules Glowatzki, Hendrik; Bröker, Benjamin; Blum, Ralf-Peter Nano Letters, Vol. 8, Issue 11 https://doi.org/10.1021/nl8021797	journal	November 2008
Rational design of two-dimensional molecular donor–acceptor nanostructure arrays Zhang, Jia Lin; Zhong, Shu; Zhong, Jian Qiang Nanoscale, Vol. 7, Issue 10 https://doi.org/10.1039/C4NR06741J	journal	January 2015
Improved Synthesis of 1,4,5,8,9,12-Hexaazatriphenylenehexacarboxylic Acid Rademacher, Jude T.; Kanakarajan, K.; Czarnik, Anthony W. Synthesis, Vol. 1994, Issue 04 https://doi.org/10.1055/s-1994-25480	journal	January 1994
Molecular/polymeric metallaynes and related molecules: Solar cell materials and devices Xu, Linli; Ho, Cheuk-Lam; Liu, Li Coordination Chemistry Reviews, Vol. 373 https://doi.org/10.1016/j.ccr.2017.10.015	journal	October 2018
WSXM : A software for scanning probe microscopy and a tool for nanotechnology Horcas, I.; Fernández, R.; Gómez-Rodríguez, J. M. Review of Scientific Instruments, Vol. 78, Issue 1 https://doi.org/10.1063/1.2432410	journal	January 2007
Energy Level Alignment and Interfacial Electronic Structures at Organic/Metal and Organic/Organic Interfaces Ishii, Hisao; Sugiyama, Kiyoshi; Ito, Eisuke Advanced Materials, Vol. 11, Issue 8, p. 605-625 https://doi.org/10.1002/(SICI)1521-4095(199906)11:8<605::AID-ADMA605>3.0.CO;2-Q	journal	June 1999
Hexaazatriphenylene doped carbon nitrides—Biomimetic photocatalyst with superior oxidation power Kurpil, Bogdan; Savateev, Aleksandr; Papaefthimiou, Vasiliki Applied Catalysis B: Environmental, Vol. 217 https://doi.org/10.1016/j.apcatb.2017.06.036	journal	November 2017

Similar Records

Frontier Orbital Degeneracy: A New Concept for Tailoring the Magnetic State in Organic Semiconductor Adsorbates

Journal Article · 2023 · Journal of Physical Chemistry. C · OSTI ID:2242391

Chakraborty, Anubhab; Zahl, Percy; Dai, Qingqing; +5 more

Efficient, Thermally Stable, and Mechanically Robust All-Polymer Solar Cells Consisting of the Same Benzodithiophene Unit-Based Polymer Acceptor and Donor with High Molecular Compatibility

Journal Article · 2020 · Advanced Energy Materials · OSTI ID:1837372

Lee, Jin‐Woo; Sun, Cheng; Ma, Boo Soo; +8 more

Distinct host-guest interaction and subdued fluorescence in a coordination network of 2,3,6,7,10,11-hexakis(phenylthio)triphenylene and silver(I) triflate

Journal Article · 2006 · Journal of Solid State Chemistry · OSTI ID:20902485

Kunhao, Li; Guo, Huang; Zhengtao, Xu; +1 more

Title: Triphenylene‐Derived Electron Acceptors and Donors on Ag(111): Formation of Intermolecular Charge‐Transfer Complexes with Common Unoccupied Molecular States

Citation Formats

References (75)

Similar Records

Related Subjects