Premium
Photocaged Competitor Guests: A General Approach Toward Light‐Activated Cargo Release From Cucurbiturils
Author(s) -
Romero Miguel A.,
Basílio Nuno,
Moro Artur J.,
Domingues Mara,
GonzálezDelgado José A.,
Arteaga Jesús F.,
Pischel Uwe
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702185
Subject(s) - cucurbituril , business , chemistry , computer science , organic chemistry , supramolecular chemistry , crystal structure
A general approach toward the light‐induced guest release from cucurbit[7]uril by means of a photoactivatable competitor was devised. An o ‐nitrobenzyl‐caged competitor is photolyzed to generate a competitive guest that can displace cargo from the host macrocycle solely based on considerations of chemical equilibrium. With this method the release of terpene guests from inclusion complexes with cucurbit[7]uril was demonstrated. The binding of the herein investigated terpenes, all being lead fragrant components in essential oils, has been characterized for the first time. They feature binding constants of up to 10 8 L mol −1 and a high differential binding selectivity (spanning four orders of magnitude for the binding constants for the particular set of terpenes). By fine‐tuning the photoactivatable competitor guest, selective and also sequential release of the terpenes was achieved.