Premium
Dynamic Nucleophilic Aromatic Substitution of Tetrazines
Author(s) -
Santos Tanausú,
Rivero David S.,
PérezPérez Yaiza,
MartínEncinas Endika,
Pasán Jorge,
Daranas Antonio Hernández,
Carrillo Romen
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106230
Subject(s) - tetrazine , moiety , chemistry , nucleophilic aromatic substitution , nucleophilic substitution , nucleophile , supramolecular chemistry , combinatorial chemistry , bioorthogonal chemistry , reagent , covalent bond , imine , dynamic covalent chemistry , aromaticity , organic chemistry , molecule , click chemistry , catalysis
A dynamic nucleophilic aromatic substitution of tetrazines (S N Tz) is presented herein. It combines all the advantages of dynamic covalent chemistry with the versatility of the tetrazine moiety. Indeed, libraries of compounds or sophisticated molecular structures can be easily obtained, which are susceptible to post‐functionalization by inverse electron demand Diels–Alder (IEDDA) reaction, which also locks the exchange. Additionally, the structures obtained can be disassembled upon the application of the right stimulus, either UV irradiation or a suitable chemical reagent. Moreover, S N Tz is compatible with the imine chemistry of anilines. The high potential of this methodology has been proved by building two responsive supramolecular systems: A macrocycle that displays a light‐induced release of acetylcholine; and a truncated [4+6] tetrahedral shape‐persistent fluorescent cage, which is disassembled by thiols unless it is post‐stabilized by IEDDA.