Template-directed synthesis of strained meso-meso-linked porphyrin nanorings

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 formatio...

Full description

Bibliographic Details
Main Authors: Van Raden, JM, Deng, J-R, Gotfredsen, H, Hergenhahn, J, Clarke, M, Edmondson, M, Hart, J, O'Shea, JN, Duarte, F, Saywell, A, Anderson, HL
Format: Journal article
Language:English
Published: Wiley 2024
Description
Summary: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.