As an extension of our studies on the multifaceted properties of C-alkylated resorc[4]arenes, we planned to immobilize on a solid support resorc[4]arenes with C11-long side chains in the lower rim. To this purpose, we synthesized two conformationally diverse resorc[4]arenes containing a bromoundecyl moiety in the four axial pendants. The cone stereoisomer 6a (30% yield) was selected for the reaction with an aminopropylated silica gel (APSG) obtained from spherical Kromasil Si 100, 5 μm particles, to give the corresponding immobilized SP-C11-resorc[4]arene system. The resulting polar-embedded stationary phase was fully characterized and investigated in the HPLC discrimination of the E/Z stereoisomers of naturally occurring and semi-synthetic combretastatins, a family of (Z)-stilbene anticancer drugs. The chair stereoisomer 6b (20% yield), when submitted to X-ray diffraction analysis, showed a noteworthy self-assembly in the crystal lattice, with intercalated hydrophobic and polar layers as a result of intermolecular Br• • •O halogen-bond interactions, according to a unique stacking motif. The potential and versatility of the SP-C11-resorc[4]arene stationary phase were shown as well in the separation of highly polar natural products (namely, flavonoids), under reversed-phase (RP) conditions, and of fullerenes C60 and C70, by using apolar solvents as mobile phases.

Synthesis of bromoundecyl resorc[4]arenes and applications of the cone stereoisomer as selector for liquid chromatography / Corradi, Silvia; Mazzoccanti, Giulia; Ghirga, Francesca; Quaglio, Deborah; Nevola, Laura; Massera, Chiara; Ugozzoli, Franco; Giannini, Giuseppe; Ciogli, Alessia; D'Acquarica, Ilaria. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - (2018). [10.1021/acs.joc.8b00488]

Synthesis of bromoundecyl resorc[4]arenes and applications of the cone stereoisomer as selector for liquid chromatography

Corradi, Silvia;Mazzoccanti, Giulia;Ghirga, Francesca;Quaglio, Deborah;Nevola, Laura;Ciogli, Alessia;D'Acquarica, Ilaria
2018

Abstract

As an extension of our studies on the multifaceted properties of C-alkylated resorc[4]arenes, we planned to immobilize on a solid support resorc[4]arenes with C11-long side chains in the lower rim. To this purpose, we synthesized two conformationally diverse resorc[4]arenes containing a bromoundecyl moiety in the four axial pendants. The cone stereoisomer 6a (30% yield) was selected for the reaction with an aminopropylated silica gel (APSG) obtained from spherical Kromasil Si 100, 5 μm particles, to give the corresponding immobilized SP-C11-resorc[4]arene system. The resulting polar-embedded stationary phase was fully characterized and investigated in the HPLC discrimination of the E/Z stereoisomers of naturally occurring and semi-synthetic combretastatins, a family of (Z)-stilbene anticancer drugs. The chair stereoisomer 6b (20% yield), when submitted to X-ray diffraction analysis, showed a noteworthy self-assembly in the crystal lattice, with intercalated hydrophobic and polar layers as a result of intermolecular Br• • •O halogen-bond interactions, according to a unique stacking motif. The potential and versatility of the SP-C11-resorc[4]arene stationary phase were shown as well in the separation of highly polar natural products (namely, flavonoids), under reversed-phase (RP) conditions, and of fullerenes C60 and C70, by using apolar solvents as mobile phases.
organic chemistry; aromatic compounds; self assembly; silica; silica gel; stereochemistry; X ray powder diffraction
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of bromoundecyl resorc[4]arenes and applications of the cone stereoisomer as selector for liquid chromatography / Corradi, Silvia; Mazzoccanti, Giulia; Ghirga, Francesca; Quaglio, Deborah; Nevola, Laura; Massera, Chiara; Ugozzoli, Franco; Giannini, Giuseppe; Ciogli, Alessia; D'Acquarica, Ilaria. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - (2018). [10.1021/acs.joc.8b00488]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1122804
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