Máximo, PatríciaColaço, MiriamPauleta, Sofia R.Costa, Paulo J.Pischel, UweParola, A. JorgeBasílio, Nuno2023-03-032023-03-032022Máximo, P., Colaço, M., Pauleta, S. R., Costa, P. J., Pischel, U., Parola, A. J., & Basílio, N. (2022). Photomodulation of ultrastable host–guest complexes in water and their application in light-controlled steroid release. In Organic Chemistry Frontiers (Vol. 9, Issue 16, pp. 4238–4249). Royal Society of Chemistry (RSC). https://doi.org/10.1039/d2qo00423b2052-4129 (electrónico)https://hdl.handle.net/10272/21709The cucurbit[8]uril (CB8) synthetic receptor is shown to form high-affinity host–guest complexes with dicationic dithienylethene (DTE) photoswitches in water. ITC experiments combined with computational studies suggest that the formation of the inclusion complexes is mainly driven by a combination of hydrophobic effects, ion–dipole, hydrogen- and chalcogen-bonding interactions. The binding affinities were observed to be much higher for the DTE closed isomers, reaching values in the picomolar range (up to 1011 M−1) while the open isomers display up to 10 000-fold lower affinities, setting ideal conditions for the development of robust photoswitchable host–guest complexes. The light-responsive affinity of these photoswitches toward CB8 was explored to control the encapsulation and release of nanomolar affinity steroids via competitive guest replacement.engAtribución-NoComercial-SinDerivadas 3.0 Españahttp://creativecommons.org/licenses/by-nc-nd/3.0/es/journal article10.1039/d2qo00423bopen access23 Química