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Long-Range Orientational Self-Assembly, Spatially Controlled Deprotonation, and Off-Centered Metalation of an Expanded Porphyrin

AuthorsCirera, Borja; Trukhina, Olga; Björk, Jonas; Bottari, Giovanni ; Rodríguez-Fernández, Jonathan; Martin-Jimenez, Alberto; Islyaikin, Mikhail K.; Otero, Roberto; Gallego, José M. ; Miranda, R.; Torres, Tomás; Ecija, David
Issue Date11-Oct-2017
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 139(40): 14129-14136 (2017)
AbstractExpanded porphyrins are large-cavity macrocycles with enormous potential in coordination chemistry, anion sensing, photodynamic therapy, and optoelectronics. In the last two decades, the surface science community has assessed the physicochemical properties of tetrapyrrolic-like macrocycles. However, to date, the sublimation, self-assembly and atomistic insights of expanded porphyrins on surfaces have remained elusive. Here, we show the self-assembly on Au(111) of an expanded aza-porphyrin, namely, an >expanded hemiporphyrazine>, through a unique growth mechanism based on long-range orientational self-assembly. Furthermore, a spatially controlled >writing> protocol on such self-assembled architecture is presented based on the STM tip-induced deprotonation of the inner protons of individual macrocycles. Finally, the capability of these surface-confined macrocycles to host lanthanide elements is assessed, introducing a novel off-centered coordination motif. The presented findings represent a milestone in the fields of porphyrinoid chemistry and surface science, revealing a great potential for novel surface patterning, opening new avenues for molecular level information storage, and boosting the emerging field of surface-confined coordination chemistry involving f-block elements.
Publisher version (URL)https://doi.org/10.1021/jacs.7b06406
Identifiersdoi: 10.1021/jacs.7b06406
e-issn: 1520-5126
issn: 0002-7863
Appears in Collections:(ICMM) Artículos
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