Porphene and porphite as porphyrin analogs of graphene and graphite

Magnera, Thomas F.; Dron, Paul I.; Bozzone, Jared P.; Jovanovic, Milena; Rončević, Igor; Tortorici, Edward; Bu, Wei; Miller, Elisa M.; Rogers, Charles T.; Michl, Josef

doi:10.1038/s41467-023-41461-w

Title: Porphene and porphite as porphyrin analogs of graphene and graphite

Journal Article · 09 October 2023 · Nature Communications

DOI: https://doi.org/10.1038/s41467-023-41461-w · OSTI ID:2204025

Magnera, Thomas F. ^[1]; Dron, Paul I. ^[2];

^[1]; Jovanovic, Milena ^[1]; Rončević, Igor ^[3]; Tortorici, Edward ^[1];

^[4];

^[5]; Rogers, Charles T. ^[6];

^[2]

Univ. of Colorado, Boulder, CO (United States)
Univ. of Colorado, Boulder, CO (United States); Czech Academy of Sciences (CAS), Prague (Czech Republic)
Czech Academy of Sciences (CAS), Prague (Czech Republic)
Univ. of Chicago, Lemont, IL (United States)
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Univ. of Colorado, Boulder, CO (United States); Renewable and Sustainable Energy Inst. (RASEI), Boulder, CO (United States)

Two-dimensional materials have unusual properties and promise applications in nanoelectronics, spintronics, photonics, (electro)catalysis, separations, and elsewhere. Most are inorganic and their properties are difficult to tune. Here we report the preparation of Zn porphene, a member of the previously only hypothetical organic metalloporphene family. Similar to graphene, these also are fully conjugated two-dimensional polymers, but are composed of fused metalloporphyrin rings. Zn porphene is synthesized on water surface by two-dimensional oxidative polymerization of a Langmuir layer of Zn porphyrin with K₂IrCl₆, reminiscent of known one-dimensional polymerization of pyrroles. It is transferable to other substrates and bridges μm-sized pits. Contrary to previous theoretical predictions of metallic conductivity, it is a p-type semiconductor due to a predicted Peierls distortion of its unit cell from square to rectangular, analogous to the appearance of bond-length alternation in antiaromatic molecules. The observed reversible insertion of various metal ions, possibly carrying a fifth or sixth ligand, promises tunability and even patterning of circuits on an atomic canvas without removing any π centers from conjugation.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); National Science Foundation (NSF); US Army Research Laboratory (USARL); US Army Research Office (ARO); Defense Advanced Research Projects Agency (DARPA); Czech Science Foundation; Czech Ministry of Education

Grant/Contract Number:: AC36-08GO28308; AC02-06CH11357; CHE-1834750; W911NF-15-1-0435; CHE 1900226; HR00111810006; ACI-1532235; ACI-1532236; 20-03691X; e-INFRA CZ, ID:90140

OSTI ID:: 2204025

Report Number(s):: NREL/JA-5900-87884; MainId:88659; UUID:3131cc12-d879-4b75-8fe6-c8867bc595c2; MainAdminID:70963

Journal Information:: Nature Communications, Vol. 14, Issue 1; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (82)

Theoretical prediction of electronic structures of fully π-conjugated zinc oligoporphyrins with curved surface structures Yamaguchi, Yoichi The Journal of Chemical Physics, Vol. 120, Issue 17 https://doi.org/10.1063/1.1690759	journal	April 2004
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
A Two‐Dimensional Polymer Synthesized at the Air/Water Interface Müller, Vivian; Hinaut, Antoine; Moradi, Mina Angewandte Chemie International Edition, Vol. 57, Issue 33 https://doi.org/10.1002/anie.201804937	journal	August 2018
Investigation of Tightly Coupled Porphyrin Arrays Comprised of Identical Monomers for Multibit Information Storage Clausen, Christian; Gryko, Daniel T.; Yasseri, Amir A. The Journal of Organic Chemistry, Vol. 65, Issue 22 https://doi.org/10.1021/jo000489e	journal	September 2000
Theoretical Prediction of a Stable 2D Crystal of Vanadium Porphyrin: A Half-Metallic Ferromagnet Singh, Harish K.; Kumar, Pawan; Waghmare, Umesh V. The Journal of Physical Chemistry C, Vol. 119, Issue 45 https://doi.org/10.1021/acs.jpcc.5b09763	journal	October 2015
Towards Designer Solids Harrison, Robin M.; Magnera, Thomas F.; Vacek, Jaroslav Modular Chemistry https://doi.org/10.1007/978-94-011-5582-3_1	book	January 1997
Theoretical study of two‐dimensionally fused zinc porphyrins: DFT calculations Yamaguchi, Yoichi International Journal of Quantum Chemistry, Vol. 109, Issue 7 https://doi.org/10.1002/qua.21998	journal	January 2009
Comparison of validity and consistency of methods for quantitative XPS peak analysis Tougaard, S.; Jansson, C. Surface and Interface Analysis, Vol. 20, Issue 13 https://doi.org/10.1002/sia.740201302	journal	December 1993
Electrocatalytic reduction of CO ₂ by two-dimensional transition metal porphyrin sheets Liu, Jin-Hang; Yang, Li-Ming; Ganz, Eric Journal of Materials Chemistry A, Vol. 7, Issue 19 https://doi.org/10.1039/C9TA01188A	journal	January 2019
The “Molecular Tinkertoy” Approach to Materials Michl, Josef Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials https://doi.org/10.1007/978-94-011-0337-4_14	book	January 1995
Adsorption of water vapour on evaporated germanium films. An Infrared Study Metcalfe, Alan; Shankar, S. Ude Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 75, Issue 0 https://doi.org/10.1039/f19797500962	journal	January 1979
Structure of a monolayer of molecular rotors on aqueous subphase from grazing-incidence X-ray diffraction Kaleta, Jiří; Wen, Jin; Magnera, Thomas F. Proceedings of the National Academy of Sciences, Vol. 115, Issue 38 https://doi.org/10.1073/pnas.1712789115	journal	March 2018
Transport properties of two‐dimensionally fused zinc porphyrins from linear‐response approach Yamaguchi, Yoichi International Journal of Quantum Chemistry, Vol. 111, Issue 12 https://doi.org/10.1002/qua.22717	journal	August 2010
Platinum complex/Zn-porphyrin macrosystem assemblies: Electronic structure and conformational investigation by x-ray photoelectron spectroscopy Polzonetti, G.; Ferri, A.; Russo, M. V. Journal of Vacuum Science & Technology A: Vacuum, Surfaces, and Films, Vol. 17, Issue 3 https://doi.org/10.1116/1.581655	journal	May 1999
Infrared attenuated total reflection spectra of adsorbed layers at the interface between a germanium electrode and an aqueous solution of sodium laurate Higashiyama, Tatsuo; Takenaka, Tohru The Journal of Physical Chemistry, Vol. 78, Issue 9 https://doi.org/10.1021/j100602a016	journal	April 1974
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
Superoxide dismutase mimetics. Part 2: synthesis and structure–Activity relationship of glyoxylate- and glyoxamide-Derived metalloporphyrins Trova, Michael P.; Gauuan, Polivina Jolicia F.; Pechulis, Anthony D. Bioorganic & Medicinal Chemistry, Vol. 11, Issue 13 https://doi.org/10.1016/S0968-0896(03)00272-4	journal	July 2003
Two-dimensional conjugated polymer films via liquid-interface-assisted synthesis toward organic electronic devices Liu, Kejun; Wang, Lihuan; Dong, Renhao Journal of Materials Chemistry C, Vol. 8, Issue 31 https://doi.org/10.1039/D0TC01586E	journal	January 2020
Chemical reactivity in organized medium: building up a two-dimensional polymer Lefevre, Didier; Porteu, Florence; Balog, Peter Langmuir, Vol. 9, Issue 1 https://doi.org/10.1021/la00025a033	journal	January 1993
Theoretical study of 1D and 2D fused magnesium porphine oligomers Charkin, O. P.; Klimenko, N. M. Russian Journal of Inorganic Chemistry, Vol. 58, Issue 9 https://doi.org/10.1134/S0036023613090064	journal	September 2013
Large Area Synthesis of a Nanoporous Two-Dimensional Polymer at the Air/Water Interface Murray, Daniel J.; Patterson, Dustin D.; Payamyar, Payam Journal of the American Chemical Society, Vol. 137, Issue 10 https://doi.org/10.1021/ja512018j	journal	March 2015
Novel pathway for homopolymerization by nuclear coupling via aromatic radical cation initiation Kovacic, Peter; England, Walter B. Journal of Polymer Science: Polymer Letters Edition, Vol. 19, Issue 7 https://doi.org/10.1002/pol.1981.130190706	journal	July 1981
Benchmarking the Performance of Time-Dependent Density Functional Theory Methods on Biochromophores Shao, Yihan; Mei, Ye; Sundholm, Dage Journal of Chemical Theory and Computation, Vol. 16, Issue 1 https://doi.org/10.1021/acs.jctc.9b00823	journal	November 2019
Graphite as an aromatic system Minot, C. The Journal of Physical Chemistry, Vol. 91, Issue 25 https://doi.org/10.1021/j100309a013	journal	December 1987
Photophysical Properties of Porphyrin Tapes Cho, Hyun Sun; Jeong, Dae Hong; Cho, Sung Journal of the American Chemical Society, Vol. 124, Issue 49 https://doi.org/10.1021/ja020826w	journal	December 2002
A novel and efficient synthesis of porphine Neya, Saburo; Quan, Jingshun; Hata, Masayuki Tetrahedron Letters, Vol. 47, Issue 49 https://doi.org/10.1016/j.tetlet.2006.10.010	journal	December 2006
Band Gap Opening by Two-Dimensional Manifestation of Peierls Instability in Graphene Lee, Sung-Hoon; Chung, Hyun-Jong; Heo, Jinseong ACS Nano, Vol. 5, Issue 4 https://doi.org/10.1021/nn1035894	journal	March 2011
Fabrication of ultra-thin 2D covalent organic framework nanosheets and their application in functional electronic devices Wang, Weikang; Zhao, Weiwei; Xu, Haotian Coordination Chemistry Reviews, Vol. 429 https://doi.org/10.1016/j.ccr.2020.213616	journal	February 2021
Self-Interaction Error in Density Functional Theory: An Appraisal Bao, Junwei Lucas; Gagliardi, Laura; Truhlar, Donald G. The Journal of Physical Chemistry Letters, Vol. 9, Issue 9 https://doi.org/10.1021/acs.jpclett.8b00242	journal	April 2018
Exploring Two-Dimensional Materials toward the Next-Generation Circuits: From Monomer Design to Assembly Control Zeng, Mengqi; Xiao, Yao; Liu, Jinxin Chemical Reviews, Vol. 118, Issue 13 https://doi.org/10.1021/acs.chemrev.7b00633	journal	January 2018
Resonance Raman spectra of deuterated metalloporphins Solovyov, K. N.; Gladkov, L. L.; Gradyushko, A. T. Journal of Molecular Structure, Vol. 45 https://doi.org/10.1016/0022-2860(78)87072-0	journal	January 1978
Spectroscopy of Cyclobutadiene Arnold, Bradley R.; Michl, Josef Kinetics and Spectroscopy of Carbenes and Biradicals https://doi.org/10.1007/978-1-4899-3707-0_1	book	January 1990
Two-dimensional polymers: concepts and perspectives Payamyar, Payam; King, Benjamin T.; Öttinger, Hans Christian Chemical Communications, Vol. 52, Issue 1 https://doi.org/10.1039/C5CC07381B	journal	January 2016
Scaled quantum mechanical and experimental vibrational spectra of magnesium and zinc porphyrins Jarzȩcki, Andrzej A.; Kozlowski, Pawel M.; Pulay, Peter Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 53, Issue 8 https://doi.org/10.1016/S1386-1425(96)01870-7	journal	July 1997
Consistent Gaussian basis sets of triple-zeta valence with polarization quality for solid-state calculations Peintinger, Michael F.; Oliveira, Daniel Vilela; Bredow, Thomas Journal of Computational Chemistry, Vol. 34, Issue 6 https://doi.org/10.1002/jcc.23153	journal	October 2012
Discrete Giant Porphyrin Arrays: Challenges to Molecular Size, Length and the Extent of Electronic π-Conjugation Aratani, Naoki; Tsuda, Akihiko; Osuka, Atsuhiro Synlett, Vol. 2001, Issue 11 https://doi.org/10.1055/s-2001-18073	journal	January 2001
A Directly Fused Tetrameric Porphyrin Sheet and Its Anomalous Electronic Properties That Arise from the Planar Cyclooctatetraene Core Nakamura, Yasuyuki; Aratani, Naoki; Shinokubo, Hiroshi Journal of the American Chemical Society, Vol. 128, Issue 12 https://doi.org/10.1021/ja057812l	journal	March 2006
Electroactive polymeric material with condensed structure on the basis of magnesium(II) polyporphine Vorotyntsev, Mikhail A.; Konev, Dmitry V.; Devillers, Charles H. Electrochimica Acta, Vol. 56, Issue 10 https://doi.org/10.1016/j.electacta.2010.10.039	journal	April 2011
Magnetic circular dichroism of an unaromatic planar [8]annulene Wen, Jin; Uto, Takayuki; Chalupský, Jakub Journal of Physical Organic Chemistry, Vol. 31, Issue 8 https://doi.org/10.1002/poc.3854	journal	May 2018
Two-dimensional supramolecular chemistry with molecular Tinkertoys Michl, J.; Magnera, T. F. Proceedings of the National Academy of Sciences, Vol. 99, Issue 8 https://doi.org/10.1073/pnas.052016299	journal	April 2002
Diboron-porphyrin monolayer: A new 2D semiconductor Tromer, Raphael M.; Felix, Isaac M.; Freitas, Aliliane Computational Materials Science, Vol. 172 https://doi.org/10.1016/j.commatsci.2019.109338	journal	February 2020
Porphine force field: in-plane normal modes of free-base porphine; comparison with metalloporphines and structural implications Li, Xiao Yuan; Zgierski, Marek Z. The Journal of Physical Chemistry, Vol. 95, Issue 11 https://doi.org/10.1021/j100164a020	journal	May 1991
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Emerging Two-Dimensional Nanomaterials for Electrocatalysis Jin, Huanyu; Guo, Chunxian; Liu, Xin Chemical Reviews, Vol. 118, Issue 13 https://doi.org/10.1021/acs.chemrev.7b00689	journal	March 2018
Two-dimensional Peierls transition with multimode lattice distortions Hamano, Tetsuya; Ono, Yoshiyuki Physica E: Low-dimensional Systems and Nanostructures, Vol. 22, Issue 1-3 https://doi.org/10.1016/j.physe.2003.11.239	journal	April 2004
The Effects of Divalent Ions on Langmuir Monolayer and Subphase Structure: A Grazing-Incidence Diffraction and Bragg Rod Study Kmetko, Jan; Datta, Alokmay; Evmenenko, Guennadi The Journal of Physical Chemistry B, Vol. 105, Issue 44 https://doi.org/10.1021/jp0122169	journal	November 2001
Quantum-mechanical condensed matter simulations with CRYSTAL Dovesi, Roberto; Erba, Alessandro; Orlando, Roberto Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 8, Issue 4 https://doi.org/10.1002/wcms.1360	journal	March 2018
Tetraphenylporphyrin monolayers: Formation at the air-water interface and characterization on glass supports by absorption and fluorescence spectroscopy Bull, Randy A.; Bulkowski, John E. Journal of Colloid and Interface Science, Vol. 92, Issue 1 https://doi.org/10.1016/0021-9797(83)90111-X	journal	March 1983
Imperfect nesting and Peierls instability for a two-dimensional tight-binding model Yuan, Q.; Nunner, T.; Kopp, T. The European Physical Journal B, Vol. 22, Issue 1 https://doi.org/10.1007/PL00011133	journal	July 2001
Wafer-sized multifunctional polyimine-based two-dimensional conjugated polymers with high mechanical stiffness Sahabudeen, Hafeesudeen; Qi, Haoyuan; Glatz, Bernhard Alexander Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13461	journal	November 2016
Interface-Assisted Synthesis of 2D Materials: Trend and Challenges Dong, Renhao; Zhang, Tao; Feng, Xinliang Chemical Reviews, Vol. 118, Issue 13 https://doi.org/10.1021/acs.chemrev.8b00056	journal	June 2018
Progress in Synthetic 2D Polymers Obtained at the Air/Water Interface Schlüter, Dieter A. CHIMIA, Vol. 73, Issue 6 https://doi.org/10.2533/chimia.2019.487	journal	July 2019
On-Surface Synthesis of Square-Type Porphyrin Tetramers with Central Antiaromatic Cyclooctatetraene Moiety Rascon, Eduardo Corral; Riss, Alexander; Matěj, Adam Journal of the American Chemical Society, Vol. 145, Issue 2 https://doi.org/10.1021/jacs.2c10088	journal	December 2022
Two‐Dimensional Boronate Ester Covalent Organic Framework Thin Films with Large Single Crystalline Domains for a Neuromorphic Memory Device Park, SangWook; Liao, Zhongquan; Ibarlucea, Bergoi Angewandte Chemie International Edition, Vol. 59, Issue 21 https://doi.org/10.1002/anie.201916595	journal	March 2020
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
First principles phonon calculations in materials science Togo, Atsushi; Tanaka, Isao Scripta Materialia, Vol. 108 https://doi.org/10.1016/j.scriptamat.2015.07.021	journal	November 2015
Single Layer of Polymeric Fe-Phthalocyanine: An Organometallic Sheet on Metal and Thin Insulating Film Abel, Mathieu; Clair, Sylvain; Ourdjini, Oualid Journal of the American Chemical Society, Vol. 133, Issue 5 https://doi.org/10.1021/ja108628r	journal	February 2011
Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared Tsuda, A. Science, Vol. 293, Issue 5527 https://doi.org/10.1126/science.1059552	journal	July 2001
Poly(zinc(ii)-5,15-porphyrinylene) from silver(i)-promoted oxidation of zinc(ii)-5,15-diarylporphyrins Yoshida, Naoya; Aratani, Naoki; Osuka, Atsuhiro Chemical Communications, Issue 3 https://doi.org/10.1039/a909444j	journal	January 2000
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
Temperature-dependent templated growth of porphine thin films on the (111) facets of copper and silver Diller, Katharina; Klappenberger, Florian; Allegretti, Francesco The Journal of Chemical Physics, Vol. 141, Issue 14 https://doi.org/10.1063/1.4896605	journal	October 2014
Carbon Nanomembranes (CNMs) Supported by Polymer: Mechanics and Gas Permeation Ai, Min; Shishatskiy, Sergey; Wind, Jan Advanced Materials, Vol. 26, Issue 21 https://doi.org/10.1002/adma.201304536	journal	February 2014
Magnesium(II) polyporphine: The first electron-conducting polymer with directly linked unsubstituted porphyrin units obtained by electrooxidation at a very low potential Vorotyntsev, Mikhail A.; Konev, Dmitry V.; Devillers, Charles H. Electrochimica Acta, Vol. 55, Issue 22 https://doi.org/10.1016/j.electacta.2010.06.001	journal	September 2010
Dehydro coupling of aromatic nuclei by catalyst-oxidant systems: poly(p-phenylene) Kovacic, Peter.; Jones, Martin B. Chemical Reviews, Vol. 87, Issue 2 https://doi.org/10.1021/cr00078a005	journal	April 1987
Chloride Molecular Doping Technique on 2D Materials: WS ₂ and MoS ₂ Yang, Lingming; Majumdar, Kausik; Liu, Han Nano Letters, Vol. 14, Issue 11 https://doi.org/10.1021/nl502603d	journal	October 2014
Stable ferromagnetism and half-metallicity in two-dimensional polyporphyrin frameworks Tan, Jie; Li, Weifeng; He, Xiujie RSC Advances, Vol. 3, Issue 19 https://doi.org/10.1039/c3ra40502h	journal	January 2013
Chemical Vapor Deposition Growth and Applications of Two-Dimensional Materials and Their Heterostructures Cai, Zhengyang; Liu, Bilu; Zou, Xiaolong Chemical Reviews, Vol. 118, Issue 13 https://doi.org/10.1021/acs.chemrev.7b00536	journal	January 2018
Synthesis of a Covalent Square Grid Magnera, Thomas F.; Pecka, Jaroslav; Michl, Josef Science and Technology of Polymers and Advanced Materials https://doi.org/10.1007/978-1-4899-0112-5_33	book	January 1998
Conductive Fused Porphyrin Tapes on Sensitive Substrates by a Chemical Vapor Deposition Approach Bengasi, Giuseppe; Baba, Kamal; Frache, Gilles Angewandte Chemie International Edition, Vol. 58, Issue 7 https://doi.org/10.1002/anie.201814034	journal	January 2019
On-surface transmetalation of metalloporphyrins Hötger, Diana; Abufager, Paula; Morchutt, Claudius Nanoscale, Vol. 10, Issue 45 https://doi.org/10.1039/C8NR04786C	journal	January 2018
Ab initio SCF studies of basis set effects in free base porphin Ghosh, Abhik; Almlöf, Jan; Gassman, Paul G. Chemical Physics Letters, Vol. 186, Issue 1 https://doi.org/10.1016/0009-2614(91)80200-H	journal	November 1991
Ab initio molecular simulations with numeric atom-centered orbitals Blum, Volker; Gehrke, Ralf; Hanke, Felix Computer Physics Communications, Vol. 180, Issue 11 https://doi.org/10.1016/j.cpc.2009.06.022	journal	November 2009
Syntheses, Structural Characterizations, and Optical and Electrochemical Properties of Directly Fused Diporphyrins Tsuda, Akihiko; Furuta, Hiroyuki; Osuka, Atsuhiro Journal of the American Chemical Society, Vol. 123, Issue 42 https://doi.org/10.1021/ja0110933	journal	October 2001
Two-Step Adsorption of PtCl ₆ ^2– Complexes at a Charged Langmuir Monolayer: Role of Hydration and Ion Correlations Uysal, Ahmet; Rock, William; Qiao, Baofu The Journal of Physical Chemistry C, Vol. 121, Issue 45 https://doi.org/10.1021/acs.jpcc.7b09350	journal	November 2017
General formulation of spin-flip time-dependent density functional theory using non-collinear kernels: Theory, implementation, and benchmarks Bernard, Yves A.; Shao, Yihan; Krylov, Anna I. The Journal of Chemical Physics, Vol. 136, Issue 20 https://doi.org/10.1063/1.4714499	journal	May 2012
Recent advances in graphene and other 2D materials Ares, Pablo; Novoselov, Kostya S. Nano Materials Science, Vol. 4, Issue 1 https://doi.org/10.1016/j.nanoms.2021.05.002	journal	March 2022
Band Structures of Periodic Porphyrin Nanostructures Posligua, Victor; Aziz, Alex; Haver, Renée The Journal of Physical Chemistry C, Vol. 122, Issue 41 https://doi.org/10.1021/acs.jpcc.8b08131	journal	June 2018
Synthesis of γ-graphyne using dynamic covalent chemistry Hu, Yiming; Wu, Chenyu; Pan, Qingyan Nature Synthesis, Vol. 1, Issue 6 https://doi.org/10.1038/s44160-022-00068-7	journal	May 2022
Oxidative coupling of porphyrins using copper(ii) salts Brennan, Bradley J.; Kenney, Michael J.; Liddell, Paul A. Chemical Communications, Vol. 47, Issue 36 https://doi.org/10.1039/c1cc13596a	journal	January 2011
Rationally synthesized two-dimensional polymers Colson, John W.; Dichtel, William R. Nature Chemistry, Vol. 5, Issue 6 https://doi.org/10.1038/nchem.1628	journal	May 2013
Highly Crystalline and Semiconducting Imine‐Based Two‐Dimensional Polymers Enabled by Interfacial Synthesis Sahabudeen, Hafeesudeen; Qi, Haoyuan; Ballabio, Marco Angewandte Chemie International Edition, Vol. 59, Issue 15 https://doi.org/10.1002/anie.201915217	journal	February 2020
Raman study of ion-induced defects in N -layer graphene Jorio, Ado; Lucchese, Marcia M.; Stavale, Fernando Journal of Physics: Condensed Matter, Vol. 22, Issue 33 https://doi.org/10.1088/0953-8984/22/33/334204	journal	August 2010

Similar Records

Electrochemical CO₂ Reduction over Metal-/Nitrogen-Doped Graphene Single-Atom Catalysts Modeled Using the Grand-Canonical Density Functional Theory

Journal Article · 2022 · ACS Catalysis · OSTI ID:1879981

Brimley, Paige; Almajed, Hussain; Alsunni, Yousef; +4 more

A quantitative metric for organic radical stability and persistence using thermodynamic and kinetic features

Journal Article · 2021 · Chemical Science · OSTI ID:1820512

Sowndarya S. V., Shree; St. John, Peter C.; Paton, Robert S.

Voltage-Modulated Untwist Deformations and Multispectral Optical Effects from Ion Intercalation into Chiral Ceramic Nanoparticles

Journal Article · 2023 · Advanced Materials · OSTI ID:1962224

Shao, Xiao; Zhu, Cheng; Kumar, Prashant; +8 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
36 MATERIALS SCIENCE
nanoelectronics
optoelectronics
organic materials
porphene
solar-photochemistry

Title: Porphene and porphite as porphyrin analogs of graphene and graphite

Citation Formats

References (82)

Similar Records

Related Subjects