Expanded Rosarin: A Versatile Fullerene (C60) Receptor.
J Am Chem Soc
; 139(13): 4627-4630, 2017 04 05.
Article
em En
| MEDLINE
| ID: mdl-28318261
ABSTRACT
An expanded rosarian (P3P6) with a bowl-like conformation has been prepared and characterized in a one-pot procedure that involves condensing a bispyrrole pyridine precursor (P1P2) with benzaldehyde, followed by oxidation. Single crystal X-ray diffraction analysis reveals a bowl-like conformation in the solid state with an upper rim diameter defined by the meso-phenyl substituents of ca. 13.5 Å and a depth of roughly 6.3 Å. P3P6 forms both 11 and 21 complexes with C60 in the solid state. DFT reveals similar energies for the two binding modes. A 11 binding stoichiometry dominates in 1,2-dichlorobenzene-d4 at the millimolar concentrations dictated by solubility consideration. The solution phase interactions between rosarian and C60 were studied using 1H NMR, UV-vis, and femtosecond transient absorption spectroscopies in 1,2-dichlorobenzene-d4 or toluene. To our knowledge, this is the first report of an unfunctionalized porphyrinoid that forms a well-defined complex with C60 in solution as well as in solid state.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article