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Local Electronic Structure of a Single-Layer Porphyrin-Containing Covalent Organic Framework

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Department of Chemistry, University of California at Berkeley, Berkeley, California 94720, United States
Department of Physics, University of California at Berkeley, Berkeley, California 94720, United States
§ Laboratory for Computational and Theoretical Chemistry of Advanced Materials, Physical Science and Engineering Division, King Abdullah University of Science and Technology, Thuwal 23955-6900, Kingdom of Saudi Arabia
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States
# Shanghai Key Laboratory of Functional Materials Chemistry and School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, 901 Atlantic Drive NW, Atlanta, Georgia 30332-0400, United States
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
Kavli Energy NanoSciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
*W.R.D. E-mail: [email protected]
*J.-L.B. E-mail: [email protected]
*M.F.C. E-mail: [email protected]
Cite this: ACS Nano 2018, 12, 1, 385–391
Publication Date (Web):December 20, 2017
Copyright © 2017 American Chemical Society

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    We have characterized the local electronic structure of a porphyrin-containing single-layer covalent organic framework (COF) exhibiting a square lattice. The COF monolayer was obtained by the deposition of 2,5-dimethoxybenzene-1,4-dicarboxaldehyde (DMA) and 5,10,15,20-tetrakis(4-aminophenyl) porphyrin (TAPP) onto a Au(111) surface in ultrahigh vacuum followed by annealing to facilitate Schiff-base condensations between monomers. Scanning tunneling spectroscopy (STS) experiments conducted on isolated TAPP precursor molecules and the covalently linked COF networks yield similar transport (HOMO–LUMO) gaps of 1.85 ± 0.05 eV and 1.98 ± 0.04 eV, respectively. The COF orbital energy alignment, however, undergoes a significant downward shift compared to isolated TAPP molecules due to the electron-withdrawing nature of the imine bond formed during COF synthesis. Direct imaging of the COF local density of states (LDOS) via dI/dV mapping reveals that the COF HOMO and LUMO states are localized mainly on the porphyrin cores and that the HOMO displays reduced symmetry. DFT calculations reproduce the imine-induced negative shift in orbital energies and reveal that the origin of the reduced COF wave function symmetry is a saddle-like structure adopted by the porphyrin macrocycle due to its interactions with the Au(111) substrate.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsnano.7b06529.

    • Details on DFT calculations, saddle structure of porphyrin on Au(111), and DOS plots (PDF)

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