Template-Directed Synthesis of Strained meso-meso-Linked Porphyrin Nanorings.

Autor: Van Raden JM; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK., Deng JR; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK., Gotfredsen H; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK., Hergenhahn J; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK., Clarke M; School of Physics & Astronomy, University of Nottingham, Nottingham, NG7 2RD, UK., Edmondson M; School of Physics & Astronomy, University of Nottingham, Nottingham, NG7 2RD, UK., Hart J; School of Physics & Astronomy, University of Nottingham, Nottingham, NG7 2RD, UK., O'Shea JN; School of Physics & Astronomy, University of Nottingham, Nottingham, NG7 2RD, UK., Duarte F; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK., Saywell A; School of Physics & Astronomy, University of Nottingham, Nottingham, NG7 2RD, UK., Anderson HL; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, OX1 3TA, UK.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Apr 02; Vol. 63 (14), pp. e202400103. Date of Electronic Publication: 2024 Mar 01.
DOI: 10.1002/anie.202400103
Abstrakt: Strained macrocycles display interesting properties, such as conformational rigidity, often resulting in enhanced π-conjugation or enhanced affinity for non-covalent guest binding, yet they can be difficult to synthesize. Here we use computational modeling to design a template to direct the formation of an 18-porphyrin nanoring with direct meso-meso bonds between the porphyrin units. Coupling of a linear 18-porphyrin oligomer in the presence of this template gives the target nanoring, together with an unexpected 36-porphyrin ring by-product. Scanning tunneling microscopy (STM) revealed the elliptical conformations and flexibility of these nanorings on a Au(111) surface.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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