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O: Fachverband Oberflächenphysik
O 11: Surface Reactions
O 11.3: Talk
Monday, March 27, 2023, 15:30–15:45, CHE 91
On-surface synthesis of porphyrinoid monomers and dimers — •Hongxiang Xu1, Ritam Chakraborty2, Biao Yang1, Joachim Reichert1, Abhishek K. Adak2, Shobhana Narasimhan2, Johannes V. Barth1, and Anthoula C. Papageorgiou1,3 — 1Technical University of Munich, Germany — 2Jawaharlal Nehru Centre for Advanced Scientific Research, India — 3National and Kapodistrian University of Athens, Greece
Porphyrinoid molecules can incorporate a wide array of the elements of the periodic table in a chemical pocket. By engineering their coordination pocket one can tune the functional properties for catalysis, spintronics, electronics and sensors. Here we use a common natural pigment, indigo, with Fe atoms on Au(111). By a series of thermally activated reaction steps including selective C-H activation, we obtain a novel metallated porphyrinoid species with high yield. By McMurry-type coupling on the same surface, this porphyrinoid species fuses into dimers. The reaction products are identified by a combination of scanning tunnelling microscopy, bond resolving atomic force microscopy and density functional theory investigations. Our studies expand the available chemistry for on-surface synthesis of macrocyclic tetrapyrroles [1] and contribute to versatile metal-organic nanostructures with smaller coordination pockets, which are challenging to obtain via solution chemistry.
[1] E. Nardi, et al. J. Phys. Chem. C 2014, 118, 27549; Q. Fan, et al. Nat. Commun. 2019 10, 5049.