A Constrained and 'Inverted' [3+3] Salphen Macrocycle with an ortho ‐Phenylethynyl Substitution Pattern

Autor:	Tomás Torres, Maxence Urbani
Rok vydání:	2020
Předmět:	Steric effects Metalation Organic Chemistry Imine Condensation Supramolecular chemistry chemistry.chemical_element General Chemistry Zinc Catalysis chemistry.chemical_compound Crystallography chemistry Yield (chemistry) Self-assembly
Zdroj:	Repositorio Institucional del Instituto Madrileño de Estudios Avanzados en Nanociencia instname
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201904763
Popis:	A [3+3] Schiff-base salphen macrocycle (7 a) was synthesized by imine condensation between ortho-phenylenediamine and ortho-phenylethynyl-bridged bis(5-salicylaldehyde) precursors. The triangular-shaped macrocycle 7 a has a nonclassical (or "inverted") design in which the N2 O2 coordination pockets are located at the sides instead of the corners. Compound 7 a could be synthesized in a reasonably good yield (64 %) considering the steric constraints imposed by the ortho substitution pattern. Subsequent zinc metalation afforded the corresponding Zn metallomacrocycle 7 b. Spectroscopic experiments evidenced weak (7 a) to strong (7 b) self-aggregation behavior in solution. Their ability to self-organize at the supramolecular level was further studied in the solid state by AFM and TEM, which revealed the formation of large bundles of fibers with lengths of several micrometers and widths of nanometers.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::927709a3a957c325259448c9d32f5041 https://doi.org/10.1002/chem.201904763 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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