Ring-closing metathesis (RCM) catalyzed by the second-generation Grubbs catalyst has been used to synthesize resorc[4]arenes 2b–5b starting from undecenyl resorc[4]arene 1b fixed in the cone conformation. X-ray diffraction analysis revealed for the major metathesis product 3b (50% yield) a cavity-shaped architecture resembling a basket, endowed with a large (≈ 10 Å) intramolecular space, and a strong propensity to self-assembly as a supramolecular trio of heterochiral dimers. This prompted us to investigate the aggregation propensity of basket 3b also in THF/water solution by UV-visible spectroscopy. Cavitation Gibbs free energy change (NNGcav = 4.78 kcal mol–1) associated with the self-assembly of macrocycle 3b was calculated as a measure of the solvophobic interactions involved in the process.

Synthesis of a Double-Spanned Resorc[4]arene via Ring-Closing Metathesis and Calculation of Aggregation Propensity / Ghirga, Francesca; Quaglio, Deborah; Iovine, Valentina; Botta, Bruno; Pierini, Marco; Mannina, Luisa; A. P., Sobolev; F., Ugozzoli; D'Acquarica, Ilaria. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 79:(2014), pp. 11051-11060. [10.1021/jo502056v]

Synthesis of a Double-Spanned Resorc[4]arene via Ring-Closing Metathesis and Calculation of Aggregation Propensity

GHIRGA, FRANCESCA;QUAGLIO, DEBORAH;IOVINE, VALENTINA;BOTTA, Bruno;PIERINI, MARCO;MANNINA, LUISA;D'ACQUARICA, Ilaria
2014

Abstract

Ring-closing metathesis (RCM) catalyzed by the second-generation Grubbs catalyst has been used to synthesize resorc[4]arenes 2b–5b starting from undecenyl resorc[4]arene 1b fixed in the cone conformation. X-ray diffraction analysis revealed for the major metathesis product 3b (50% yield) a cavity-shaped architecture resembling a basket, endowed with a large (≈ 10 Å) intramolecular space, and a strong propensity to self-assembly as a supramolecular trio of heterochiral dimers. This prompted us to investigate the aggregation propensity of basket 3b also in THF/water solution by UV-visible spectroscopy. Cavitation Gibbs free energy change (NNGcav = 4.78 kcal mol–1) associated with the self-assembly of macrocycle 3b was calculated as a measure of the solvophobic interactions involved in the process.
2014
Resorc[4]arene derivative; Metathesis reaction; Aggregation Propensity
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of a Double-Spanned Resorc[4]arene via Ring-Closing Metathesis and Calculation of Aggregation Propensity / Ghirga, Francesca; Quaglio, Deborah; Iovine, Valentina; Botta, Bruno; Pierini, Marco; Mannina, Luisa; A. P., Sobolev; F., Ugozzoli; D'Acquarica, Ilaria. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 79:(2014), pp. 11051-11060. [10.1021/jo502056v]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/615616
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