Porphyrin-fused graphene nanoribbons.
Journal
Nature chemistry
ISSN: 1755-4349
Titre abrégé: Nat Chem
Pays: England
ID NLM: 101499734
Informations de publication
Date de publication:
08 Mar 2024
08 Mar 2024
Historique:
received:
02
03
2023
accepted:
15
02
2024
medline:
9
3
2024
pubmed:
9
3
2024
entrez:
8
3
2024
Statut:
aheadofprint
Résumé
Graphene nanoribbons (GNRs), nanometre-wide strips of graphene, are promising materials for fabricating electronic devices. Many GNRs have been reported, yet no scalable strategies are known for synthesizing GNRs with metal atoms and heteroaromatic units at precisely defined positions in the conjugated backbone, which would be valuable for tuning their optical, electronic and magnetic properties. Here we report the solution-phase synthesis of a porphyrin-fused graphene nanoribbon (PGNR). This PGNR has metalloporphyrins fused into a twisted fjord-edged GNR backbone; it consists of long chains (>100 nm), with a narrow optical bandgap (~1.0 eV) and high local charge mobility (>400 cm
Identifiants
pubmed: 38459234
doi: 10.1038/s41557-024-01477-1
pii: 10.1038/s41557-024-01477-1
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council)
ID : 885606 ARO-MAT
Organisme : EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council)
ID : 885606 ARO-MAT
Organisme : EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council)
ID : ERC-CoG-773048-MMGNR
Organisme : EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council)
ID : Pathfinder-101099676-4D-NMR
Organisme : RCUK | Engineering and Physical Sciences Research Council (EPSRC)
ID : EP/N014995/1
Organisme : RCUK | Engineering and Physical Sciences Research Council (EPSRC)
ID : EP/N017188/1
Organisme : RCUK | Engineering and Physical Sciences Research Council (EPSRC)
ID : EP/R029229/1
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 514772236
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 431450789
Organisme : Deutsche Forschungsgemeinschaft (German Research Foundation)
ID : 431450789
Informations de copyright
© 2024. The Author(s).
Références
Nakada, K., Fujita, M., Dresselhaus, G. & Dresselhaus, M. S. Edge state in graphene ribbons: nanometer size effect and edge shape dependence. Phys. Rev. B 54, 17954–17961 (1996).
doi: 10.1103/PhysRevB.54.17954
Son, Y. W., Cohen, M. L. & Louie, S. G. Energy gaps in graphene nanoribbons. Phys. Rev. Lett. 97, 216803 (2006).
pubmed: 17155765
doi: 10.1103/PhysRevLett.97.216803
Houtsma, R. S. K., de la Rie, J. & Stohr, M. Atomically precise graphene nanoribbons: interplay of structural and electronic properties. Chem. Soc. Rev. 50, 6541–6568 (2021).
pubmed: 34100034
pmcid: 8185524
doi: 10.1039/D0CS01541E
Wang, H. et al. Graphene nanoribbons for quantum electronics. Nat. Rev. Phys. 3, 791–802 (2021).
doi: 10.1038/s42254-021-00370-x
Jiao, L., Wang, X., Diankov, G., Wang, H. & Dai, H. Facile synthesis of high-quality graphene nanoribbons. Nat. Nanotechnol. 5, 321–325 (2010).
pubmed: 20364133
doi: 10.1038/nnano.2010.54
Chen, C. et al. Sub-10-nm graphene nanoribbons with atomically smooth edges from squashed carbon nanotubes. Nat. Electron. 4, 653–663 (2021).
doi: 10.1038/s41928-021-00633-6
Kosynkin, D. V. et al. Longitudinal unzipping of carbon nanotubes to form graphene nanoribbons. Nature 458, 872–876 (2009).
pubmed: 19370030
doi: 10.1038/nature07872
Gu, Y., Qiu, Z. & Müllen, K. Nanographenes and graphene nanoribbons as multitalents of present and future materials science. J. Am. Chem. Soc. 144, 11499–11524 (2022).
pubmed: 35671225
pmcid: 9264366
doi: 10.1021/jacs.2c02491
Narita, A., Chen, Z., Chen, Q. & Müllen, K. Solution and on-surface synthesis of structurally defined graphene nanoribbons as a new family of semiconductors. Chem. Sci. 10, 964–975 (2019).
pubmed: 30774890
pmcid: 6349060
doi: 10.1039/C8SC03780A
Wang, X., Narita, A. & Müllen, K. Precision synthesis versus bulk-scale fabrication of graphenes. Nat. Rev. Chem. 2, 0100 (2017).
doi: 10.1038/s41570-017-0100
Llinas, J. P. et al. Short-channel field-effect transistors with 9-atom and 13-atom wide graphene nanoribbons. Nat. Commun. 8, 633 (2017).
pubmed: 28935943
pmcid: 5608806
doi: 10.1038/s41467-017-00734-x
Cai, J. et al. Graphene nanoribbon heterojunctions. Nat. Nanotechnol. 9, 896–900 (2014).
pubmed: 25194948
doi: 10.1038/nnano.2014.184
Ma, C. et al. Engineering edge states of graphene nanoribbons for narrow-band photoluminescence. ACS Nano 14, 5090–5098 (2020).
pubmed: 32283017
doi: 10.1021/acsnano.0c01737
Mateo, L. M. et al. On-surface synthesis of singly and doubly porphyrin-capped graphene nanoribbon segments. Chem. Sci. 12, 247–252 (2020).
pubmed: 34163593
pmcid: 8178705
doi: 10.1039/D0SC04316H
Mateo, L. M. et al. On-surface synthesis and characterization of triply fused porphyrin-graphene nanoribbon hybrids. Angew. Chem. Int. Ed. 59, 1334–1339 (2020).
doi: 10.1002/anie.201913024
Su, X., Xue, Z., Li, G. & Yu, P. Edge state engineering of graphene nanoribbons. Nano Lett. 18, 5744–5751 (2018).
pubmed: 30111118
doi: 10.1021/acs.nanolett.8b02356
Li, G. et al. A modular synthetic approach for band-gap engineering of armchair graphene nanoribbons. Nat. Commun. 9, 1687 (2018).
pubmed: 29703958
pmcid: 5924368
doi: 10.1038/s41467-018-03747-2
Iancu, V., Deshpande, A. & Hla, S. W. Manipulating Kondo temperature via single molecule switching. Nano Lett. 6, 820–823 (2006).
pubmed: 16608290
doi: 10.1021/nl0601886
Sedghi, G. et al. Long-range electron tunnelling in oligo-porphyrin molecular wires. Nat. Nanotechnol. 6, 517–523 (2011).
pubmed: 21804555
doi: 10.1038/nnano.2011.111
Winters, M. U. et al. Probing the efficiency of electron transfer through porphyrin-based molecular wires. J. Am. Chem. Soc. 129, 4291–4297 (2007).
pubmed: 17362004
doi: 10.1021/ja067447d
Peeks, M. D. et al. Electronic delocalization in the radical cations of porphyrin oligomer molecular wires. J. Am. Chem. Soc. 139, 10461–10471 (2017).
pubmed: 28678489
pmcid: 5543395
doi: 10.1021/jacs.7b05386
Wende, H. et al. Substrate-induced magnetic ordering and switching of iron porphyrin molecules. Nat. Mater. 6, 516–520 (2007).
pubmed: 17558431
doi: 10.1038/nmat1932
Cho, W. J., Cho, Y., Min, S. K., Kim, W. Y. & Kim, K. S. Chromium porphyrin arrays as spintronic devices. J. Am. Chem. Soc. 133, 9364–9369 (2011).
pubmed: 21612202
doi: 10.1021/ja111565w
Li, J. et al. Survival of spin state in magnetic porphyrins contacted by graphene nanoribbons. Sci. Adv. 4, eaaq0582 (2018).
pubmed: 29464209
pmcid: 5815864
doi: 10.1126/sciadv.aaq0582
Li, J. et al. Electrically addressing the spin of a magnetic porphyrin through covalently connected graphene electrodes. Nano Lett. 19, 3288–3294 (2019).
pubmed: 30964303
doi: 10.1021/acs.nanolett.9b00883
Tsuda, A. & Osuka, A. Fully conjugated porphyrin tapes with electronic absorption bands that reach into infrared. Science 293, 79–82 (2001).
pubmed: 11441176
doi: 10.1126/science.1059552
Leary, E. et al. Bias-driven conductance increase with length in porphyrin tapes. J. Am. Chem. Soc. 140, 12877–12883 (2018).
pubmed: 30207150
doi: 10.1021/jacs.8b06338
He, Y. et al. Fusing tetrapyrroles to graphene edges by surface-assisted covalent coupling. Nat. Chem. 9, 33–38 (2017).
pubmed: 27995925
doi: 10.1038/nchem.2600
Chen, Q. et al. Synthesis of triply fused porphyrin-nanographene conjugates. Angew. Chem. Int. Ed. 57, 11233–11237 (2018).
doi: 10.1002/anie.201805063
Yao, X. et al. Synthesis of nonplanar graphene nanoribbon with fjord edges. J. Am. Chem. Soc. 143, 5654–5658 (2021).
pubmed: 33825484
pmcid: 8154539
doi: 10.1021/jacs.1c01882
Narita, A. et al. Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons. Nat. Chem. 6, 126–132 (2014).
pubmed: 24451588
doi: 10.1038/nchem.1819
Li, Y. L. et al. Fjord-edge graphene nanoribbons with site-specific nitrogen substitution. J. Am. Chem. Soc. 142, 18093–18102 (2020).
pubmed: 32894950
doi: 10.1021/jacs.0c07657
Ma, S. et al. Supertwistacene: a helical graphene nanoribbon. J. Am. Chem. Soc. 142, 16887–16893 (2020).
pubmed: 32900184
doi: 10.1021/jacs.0c08555
Daigle, M., Miao, D., Lucotti, A., Tommasini, M. & Morin, J. F. Helically coiled graphene nanoribbons. Angew. Chem. Int. Ed. 56, 6213–6217 (2017).
doi: 10.1002/anie.201611834
Martin, M. M., Oleszak, C., Hampel, F. & Jux, N. Oxidative cyclodehydrogenation reactions with tetraarylporphyrins. Eur. J. Org. Chem. 2020, 6758–6762 (2020).
doi: 10.1002/ejoc.202001174
Ulbricht, R., Hendry, E., Shan, J., Heinz, T. F. & Bonn, M. Carrier dynamics in semiconductors studied with time-resolved terahertz spectroscopy. Rev. Mod. Phys. 83, 543–586 (2011).
doi: 10.1103/RevModPhys.83.543
Zhang, H. et al. Highly mobile hot holes in Cs
pubmed: 34936431
pmcid: 8694595
doi: 10.1126/sciadv.abj9066
Hendry, E., Schins, J. M., Candeias, L. P., Siebbeles, L. D. & Bonn, M. Efficiency of exciton and charge carrier photogeneration in a semiconducting polymer. Phys. Rev. Lett. 92, 196601 (2004).
pubmed: 15169428
doi: 10.1103/PhysRevLett.92.196601
Tries, A. et al. Experimental observation of strong exciton effects in graphene nanoribbons. Nano Lett. 20, 2993–3002 (2020).
pubmed: 32207957
pmcid: 7311082
doi: 10.1021/acs.nanolett.9b04816
Piet, J. J. et al. Photoexcitations of covalently bridged zinc porphyrin oligomers: Frenkel versus Wannier−Mott type excitons. J. Phys. Chem. B 105, 97–104 (2000).
doi: 10.1021/jp0030140
Smith, N. V. Drude theory and the optical properties of liquid mercury. Phys. Lett. A 26, 126–127 (1968).
doi: 10.1016/0375-9601(68)90513-6
Ivanov, I. et al. Role of edge engineering in photoconductivity of graphene nanoribbons. J. Am. Chem. Soc. 139, 7982–7988 (2017).
pubmed: 28525278
doi: 10.1021/jacs.7b03467
Jensen, S. A. et al. Ultrafast photoconductivity of graphene nanoribbons and carbon nanotubes. Nano Lett. 13, 5925–5930 (2013).
pubmed: 24093134
doi: 10.1021/nl402978s
Wang, X. et al. Cove-edged graphene nanoribbons with incorporation of periodic zigzag-edge segments. J. Am. Chem. Soc. 144, 228–235 (2022).
pubmed: 34962807
doi: 10.1021/jacs.1c09000
Niu, W. et al. Exceptionally clean single-electron transistors from solutions of molecular graphene nanoribbons. Nat. Mater. 22, 180–185 (2023).
pubmed: 36732344
pmcid: 10208969
doi: 10.1038/s41563-022-01460-6
Mol, J. A. et al. Graphene-porphyrin single-molecule transistors. Nanoscale 7, 13181–13185 (2015).
pubmed: 26185952
doi: 10.1039/C5NR03294F
Pei, T. et al. Exchange-induced spin polarization in a single magnetic molecule junction. Nat. Commun. 13, 4506 (2022).
pubmed: 35922414
pmcid: 9349289
doi: 10.1038/s41467-022-31909-w
Weitz, R. T. et al. High-performance carbon nanotube field effect transistors with a thin gate dielectric based on a self-assembled monolayer. Nano Lett. 7, 22–27 (2007).
pubmed: 17212434
doi: 10.1021/nl061534m
Shylau, A. A., Kłos, J. W. & Zozoulenko, I. V. Capacitance of graphene nanoribbons. Phys. Rev. B 80, 205402 (2009).
doi: 10.1103/PhysRevB.80.205402
Fu, H. et al. Doping-induced giant rectification and negative differential conductance (NDC) behaviors in zigzag graphene nano-ribbon junction. Phys. Lett. A 383, 867–872 (2019).
doi: 10.1016/j.physleta.2018.12.001
Peersen, O. B., Wu, X. L., Kustanovich, I. & Smith, S. O. Variable-amplitude cross-polarization MAS NMR. J. Magn. Reson. A 104, 334–339 (1993).
doi: 10.1006/jmra.1993.1231
Cory, D. G. & Ritchey, W. M. Suppression of signals from the probe in bloch decay spectra. J. Magn. Reson. 80, 128–132 (1988).
Feike, M. et al. Broadband multiple-quantum NMR spectroscopy. J. Magn. Reson. A 122, 214–221 (1996).
doi: 10.1006/jmra.1996.0197
Limburg, B. et al. Anchor groups for graphene-porphyrin single-molecule transistors. Adv. Funct. Mater. 28, 1803629 (2018).
doi: 10.1002/adfm.201803629
Frisch, M. J. et al. Gaussian 16, Revision C.01 (Gaussian, Inc., 2016).