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Surface-Assisted Cyclodehydrogenation; Break the Symmetry, Enhance the Selectivity

DOI: 10.1002/chem.201502001 DOI Help
PMID: 26211450 PMID Help

Authors: Alissa Wiengarten (Technische Universität München) , Julian A. Lloyd (Technische Universität München) , Knud Seufert (Technische Universität München) , Joachim Reichert (Technische Universität München) , Willi Auwärter (Technische Universität München) , Runyuan Han (Technische Universität München) , David A Duncan (Diamond Light Source) , Francesco Allegretti (TU Munich) , Sybille Fischer (Technische Universität München) , Seung Cheol Oh (Technische Universität München) , Özge Sağlam (Technische Universität München) , Li Jiang (Technische Universität München) , Saranyan Vijayaraghavan (Technische Universität München) , David Écija (Technische Universität München) , Anthoula C. Papageorgiou (Technische Universität München) , Johannes V. Barth (Technische Universität München)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry - A European Journal , VOL 21 , PAGES 12285 - 12290

State: Published (Approved)
Published: August 2015

Abstract: Selectivity in chemical reactions is a major objective in industrial processes to minimize spurious byproducts and to save scarce resources. In homogeneous catalysis the most important factor which determines selectivity is structural symmetry. However, a transfer of the symmetry concept to heterogeneous catalysis still requires a detailed comprehension of the underlying processes. Here, we investigate a ring-closing reaction in surface-confined meso-substituted porphyrin molecules by scanning tunneling microscopy, temperature-programmed desorption, and computational modeling. The identification of reaction intermediates enables us to analyze the reaction pathway and to conclude that the symmetry of the porphyrin core is of pivotal importance regarding product yields.

Journal Keywords: heterogeneous catalysis;porphyrins;ring-closing reaction;selectivity;symmetry

Subject Areas: Chemistry


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