Naslov
Exploring the bright side of hydrophobically driven complexation: the bitter synthesis of sweet fluorescent amphiphiles

Autori
Usenik, Andrea ; Poljanić, Leon ; Radonić, Doroteja ; Pičuljan, Katarina ; Car, Željka ; Petrović Peroković, Vesna ; Požar, Josip

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

Izvornik
Adriatic NMR Conference 2021 : Book of abstracts / Bregović, Nikola ; Namjesnik, Danijel ; Novak, Predrag ; Parlov Vuković, Jelena - Zagreb : Hrvatsko kemijsko društvo, 2021, 62-62

Skup
The Adriatic NMR Conference 2021

Mjesto i datum
Primošten, Hrvatska, 13.09.2021. - 15.09.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
Hydrophobic effect ; solvophobic effect ; inclusion complex ; complexation thermodynamics ; cyclodextrins ; cucurbit[7]uril ; mannoconjugates

Sažetak
Regioisomeric mannoconjugates of naphthyl alcohols were synthesized by coupling of protected mannopyranose and corresponding esters of bromoacetic acid with 1- and 2- naphthyl moieties. Their complexation and the complexation of corresponding nonfunctionalized alcohols with cyclodextrins (α-, β- and γ-) and cucurbit[7]uril was explored by means of isothermal titration calorimetry, spectrophotometry, fluorimetry and NMR spectroscopy. The complexation of 2- naphthol with cucurbit[7]uril was thermodynamically most favorable. A pronounced temperature dependence of ΔrH° and ΔrS°, resulting in an almost complete enthalpy- entropy compensation was observed for some of the examined host-guest systems. In these cases, the complexation thermodynamics was in line with the classical rationale of the hydrophobic effect at lower temperatures, and the non-classical explanation at higher ones. The results of 1H NMR titrations and ROESY experiments were in agreement with the results obtained by other experimental methods and have revealed an interesting difference in complex formation kinetics among the investigated host molecules.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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