Affiliation:
1. Julius-Maximilians-Universität Würzburg Institut für Organische Chemie Am Hubland 97074 Würzburg Germany
2. Julius-Maximilians-Universität Würzburg Center for Nanosystems Chemistry (CNC) Theodor-Boveri-Weg 97074 Würzburg Germany
3. Eberhard Karls Universität Tübingen Institut für Organische Chemie Auf der Morgenstelle 18 72076 Tübingen Germany
Abstract
AbstractReliable structure elucidation of covalent organic cage compounds remains challenging as routine analysis might leave ambiguities. Diffusion‐ordered NMR spectroscopy (DOSY) allows insight into the molecular size and mass of the species present in solution, but a systematic evaluation of the diffusion behavior for cage assemblies is rarely considered. Here we report the synthesis of four series of covalent organic cages based on tribenzotriquinacenes and diboronic acids with varying geometry and exohedral substituents. We provide a guideline for the consistent measurement of diffusion coefficients from 1H‐DOSY NMR spectroscopy, which was utilized to study the diffusion behavior for the whole set of cages and selected examples from the literature. For structurally similar cages, a linear correlation between the solvodynamic volume and the molecular mass allows precise size determination. For more complex systems, multiple parameters, such as window size or rigid exohedral functionalization. further modulate cage diffusion in solution.
Funder
Deutsche Forschungsgemeinschaft
Bayerisches Staatsministerium für Wissenschaft, Forschung und Kunst
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
5 articles.
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