Hydrazone exchange: a viable route for the solid-tethered synthesis of [2]rotaxanes

Autor:	Rafael Da Silva Rodrigues, David L. Marshall, John C. McMurtrie, Kathleen M. Mullen, Ena T. Luis
Rok vydání:	2021
Předmět:	chemistry.chemical_classification 1h nmr spectroscopy Rotaxane Covalent bond Chemistry Solid surface Materials Chemistry Supramolecular chemistry Hydrazone General Chemistry Polymer Combinatorial chemistry Catalysis
Zdroj:	New Journal of Chemistry. 45:4414-4421
ISSN:	1369-9261 1144-0546
DOI:	10.1039/d1nj00388g
Popis:	Controlled and complete assembly of supramolecular systems on solid supports is a challenge that would elevate the function of interlocked architectures. Building on the success of other dynamic covalent synthetic methods, we present hydrazone exchange as a strategy to improve the formation of rotaxanes in solution and on solid surfaces. Solution-state analogues containing naphthalenediimide (NDI) or bipyridinium motifs and 1,5-dinaphtho[38]crown-10 were initially prepared to establish ideal conditions for maintaining thermal equilibrium throughout the exchange reaction. Solid-state rotaxanes were synthesised on hydrazide-functionalised TentaGel™ polymer resins and analysed with HR MAS 1H NMR spectroscopy. Surface rotaxane functionalisation of 80% was achieved for the NDI rotaxane, which is significantly higher than previously reported with either dynamic covalent or traditional irreversible synthetic strategies.
Databáze:	OpenAIRE
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