title: Synthesis of a double-spanned resorc[4]arene via ring-closing metathesis and calculation of aggregation propensity.
abstract: Ring-closing metathesis (RCM) catalyzed by a 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 of the major metathesis product, 3b (50% yield), revealed a cavity-shaped architecture resembling a basket, endowed with a large intramolecular space (∼10 Å) and a strong propensity to self-assemble as a supramolecular trio of heterochiral dimers. This prompted us to investigate the aggregation propensity of basket 3b in THF/water solution by UV-visible spectroscopy. The cavitation Gibbs free-energy change (ΔΔGcav = 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.
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Ghirga
authors.forename: Deborah
authors.initials: D
authors.lastname: Quaglio
authors.forename: Valentina
authors.initials: V
authors.lastname: Iovine
authors.forename: Bruno
authors.initials: B
authors.lastname: Botta
authors.forename: Marco
authors.initials: M
authors.lastname: Pierini
authors.forename: Luisa
authors.initials: L
authors.lastname: Mannina
authors.forename: Anatoly P
authors.initials: AP
authors.lastname: Sobolev
authors.forename: Franco
authors.initials: F
authors.lastname: Ugozzoli
authors.forename: Ilaria
authors.initials: I
authors.lastname: D'Acquarica