ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
Vernier-templated synthesis, crystal structure, and supramolecular chemistry of a 12-porphyrin nanoring.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 53 citations in OpenAlex.
- Knotting matters: orderly molecular entanglements.Chemical Society reviews · 2022Review
- Ordering, flexibility and frustration in arrays of porphyrin nanorings.Nature communications · 2019Article
- On-Surface Synthesis within a Porphyrin Nanoring Template.Scientific reports · 2019Article
- Template-directed synthesis of linear porphyrin oligomers: classical, Vernier and mutual Vernier.Chemical science · 2017Article
- Crystal Fluidity Reflected by Fast Rotational Motion at the Core, Branches, and Peripheral Aromatic Groups of a Dendrimeric Molecular Rotor.Journal of the American Chemical Society · 2016Article
- Caterpillar Track Complexes in Template-Directed Synthesis and Correlated Molecular Motion.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2015Article
- Caterpillar track complexes in template-directed synthesis and correlated molecular motion.Angewandte Chemie (International ed. in English) · 2015Article
- Structure-Directed Exciton Dynamics in Templated Molecular Nanorings.The journal of physical chemistry. C, Nanomaterials and interfaces · 2015Article
- Crystal structures of increasingly large molecules: meeting the challenges with CRYSTALS software.Chemistry Central journal · 2015Article
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Authors and funding
10 authors at 3 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Vernier templating exploits a mismatch between the number of binding sites in a template and a reactant to direct the formation of a product that is large enough to bind several template units. Here, we present a detailed study of the Vernier-templated synthesis of a 12-porphyrin nanoring. NMR and small-angle X-ray scattering (SAXS) analyses show that Vernier complexes are formed as intermediates in the cyclo-oligomerization reaction. UV/Vis/NIR titrations show that the three-component assembly of the 12-porphyrin nanoring figure-of-eight template complex displays high allosteric cooperativity and chelate cooperativity. This nanoring-template 1:2 complex is among the largest synthetic molecules to have been characterized by single-crystal analysis. It crystallizes as a racemate, with an angle of 27° between the planes of the two template units. The crystal structure reveals many unexpected intramolecular C-H⋅⋅⋅N contacts involving the tert-butyl side chains. Scanning tunneling microscopy (STM) experiments show that molecules of the 12-porphyrin template complex can remain intact on the gold surface, although the majority of the material unfolds into the free nanoring during electrospray deposition.
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