Challenges in the synthesis of corannulene-based non-planar nanographenes on Au(111) surfaces

Wang, Tao; Lawrence, James; Sumi, Naoya; Robles, Roberto; Castro‐Esteban, Jesús; Rey, Dulce; Mohammed, Mohammed S. G.; Berdonces‐Layunta, Alejandro; Lorente, Nicolás; Pérez, Dolores; Peña, Diego; Corso, Martina; Oteyza, Dimas G. de

doi:10.1039/d1cp01212f

Cited by 2 publications

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“…A comparison between the apparent height of the biradical biphenylene monomer and the final biphenylene dimer product on Ag(111) is presented in Figure S3, where a difference of 1.8 Å was obtained. The perpendicular adsorption configuration also explained the formation of trimers and tetramers in parts d and e of Figure , respectively, which should be stabilized by π–π stacking between face-to-face phenyls. − The DFT-calculated structural models of the trimer and the tetramer are displayed in parts f and g of Figure , respectively. The distance between two adjacent molecules was ∼7.8 Å for both the trimer and the tetramer, which was in excellent agreement with the experimental value (Figure e).…”

Section: Resultsmentioning

confidence: 96%

Chemisorption-Induced Formation of Biphenylene Dimer on Ag(111)

et al. 2021

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We report an example that demonstrates the clear interdependence between surface-supported reactions and molecular-adsorption configurations. Two biphenyl-based molecules with two and four bromine substituents, i.e., 2,2′dibromobiphenyl (DBBP) and 2,2′,6,6′-tetrabromo-1,1′-biphenyl (TBBP), show completely different reaction pathways on a Ag(111) surface, leading to the selective formation of dibenzo[e,l]pyrene and biphenylene dimer, respectively. By combining low-temperature scanning tunneling microscopy, synchrotron radiation photoemission spectroscopy, and density functional theory calculations, we unravel the underlying reaction mechanism. After debromination, a biradical biphenyl can be stabilized by surface Ag adatoms, while a four-radical biphenyl undergoes spontaneous intramolecular annulation due to its extreme instability on Ag(111). Such different chemisorption-induced precursor states between DBBP and TBBP consequently lead to different reaction pathways after further annealing. In addition, using bond-resolving scanning tunneling microscopy and scanning tunneling spectroscopy, we determine with atomic precision the bond-length alternation of the biphenylene dimer product, which contains 4-, 6-, and 8-membered rings. The 4-membered ring units turn out to be radialene structures.

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Section: Resultsmentioning

confidence: 96%