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

Alissa Wiengarten, Julian A. Lloyd, Knud Seufert, Joachim Reichert, Willi Auwärter, Runyuan Han, David A. Duncan, Francesco Allegretti, Sybille Fischer, Seung Cheol Oh, Özge Saʇlam, Li Jiang, Saranyan Vijayaraghavan, David Écija, Anthoula C. Papageorgiou, Johannes V. Barth

Research output: Contribution to journalArticlepeer-review

54 Scopus citations


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.

Original languageEnglish
Pages (from-to)12285-12290
Number of pages6
JournalChemistry - A European Journal
Issue number35
StatePublished - 1 Aug 2015


  • heterogeneous catalysis
  • porphyrins
  • ring-closing reaction
  • selectivity
  • symmetry


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