Naslov
Calix[6]arene threading: from Scarcerly to More Preorganized Wheels

Autori
Iuliano, Veronica ; Tranfić Bakić, Marina ; Talotta, Carmen ; Soriente, Annunziata ; De Rosa, Margherita ; Gaeta, Carmine ; Neri, Placido

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
14th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC) Book of Abstracts / - Lecce, 2019, P207-P207

Skup
14th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2019)

Mjesto i datum
Lecce, Italija, 02.06.2019. - 06.06.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
kaliksaren ; udjenjivanje ; kompleksiranje ; pseudorotaksani
(caixarene ; threading ; complexation ; pseudorotaxanes)

Sažetak
The principle of preorganization has become a cornerstone in supramolecular chemistry, because it is used to design highly efficient hosts able to recognize specific guests. In 2010, we reported that scarcerly preorganized (conformationaly mobile) calix[6]arene derivatives were threaded by dialkylammonium axles only when the ammonium cation was associated to the weakly coordinating superweak anion: "the Tetrakis[3, 5- bis(triFluoromethyl)Phenyl]Borate (TFPB-)". In addition, it was observed that the efficiency of the threading was closely associated with the conformational stability of the calix-wheel. Thus, the calix[6]-wheel 1b bearing longer hexyl chains at the lower rim, was threaded by all of the dialkylammonium axles 2-4, more tightly than 1a, as a result of its higher degree of preorganization. Very recently, has been reported a new strategy for the preorganization of calix[6]arene which exploits the functionalization of the methylene bridges (ArCH2Ar) and affords to the formation of stable calix[6]arene cone-conformers. On the basis of these considerations, now the question arises as to wether the calix[6]-wheels 5a-c bearing alkyl groups at the methylene bridges, are also capable of threading with dialkylammonium axles 2-4. In addition, in the present work, we will describe the role played by conformational stability of the derivatives 5a-c on the thermodynamic stability of the respective pseudorotaxanes. Finally, self-sorting experiments with 2+ and calix[6]-wheels 1 and 5 at different degree of preorganization, will be reported.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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