Quinones and Heteroatom Analogues

Griesbeck, Axel G.; Vong, B. G.; Theodorakis, Emmanuel A.; Balci, M.; Çelik, M.; Gültekin, M. S.; Kim, S. H.; Lee, H.; Nair, Vijay; Radhakrishnan, K. V.; Couladouros, Elias A.; Strongilos, A. T.; Liao, Chi Chang; Peddinti, Rama Krishna; Krohn, Karsten; Böker, N.; Echavarren, Antonio M.; Porcel, S.; Pindur, U.; Lemster, T.; Yoshifuji, Masaaki; Kawasaki, Satoshi; Carreño, M. Carmen; Ribagorda, María; Avendaño, Carmen; Menéndez, J. Carlos; Zimmermann, Elke; Pettus, Thomas R. R.; Selenski, C.

doi:10.1055/sos-sd-028-00000

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“…Quinone and quinone imines in general, and 1,4‐benzoquinone monoimine in particular, are very useful building blocks for the synthesis of a wide variety of compounds, [1] from natural products to polymers, with a broad range of applications. Despite the a priori structural simplicity of such molecules, they are characterized by a lack of control of the reactive sites due to the electrophilic character of the different positions on the ring (see positions 2, 3, 4, and 5 in equation a, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

On‐Surface Driven Formal Michael Addition Produces m‐Polyaniline Oligomers on Pt(111)

et al. 2020

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On-surface synthesis is emerging as a highly rational bottom-up methodology for the synthesis of molecular structures that are unattainable or complex to obtain by wet chemistry. Here, oligomers of meta-polyaniline, a known ferromagnetic polymer, were synthesized from para-amino-phenol building-blocks via an unexpected and highly specific on-surface formal 1,4 Michael-type addition at the meta position, driven by the reduction of the aminophenol molecule. We rationalize this dehydrogenation and coupling reaction mechanism with a combination of in situ scanning tunneling and non-contact atomic force microscopies, high-resolution synchrotron-based X-ray photoemission spectroscopy and first-principles calculations. This study demonstrates the capability of surfaces to selectively modify local molecular conditions to redirect well-established synthetic routes, such as Michael coupling, towards the rational synthesis of new covalent nanostructures.

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Section: Introductionmentioning

confidence: 99%