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“Design of Experiments” as a Method to Optimize Dynamic Disulfide Assemblies: Cages and Functionalizable Macrocycles
Author(s) -
Shear Trevor A.,
Lin Fuding,
Zakharov Lev N.,
Johnson Darren W.
Publication year - 2020
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.201912169
Subject(s) - disulfide bond , yield (engineering) , dynamic covalent chemistry , covalent bond , functional group , reaction conditions , cage , combinatorial chemistry , chemistry , materials science , nanotechnology , computer science , molecule , organic chemistry , mathematics , supramolecular chemistry , biochemistry , metallurgy , catalysis , polymer , combinatorics
Cyclophanes are a venerable class of macrocyclic and cage compounds that often contain unusual conformations, high strain, and unusual properties. However, synthesis of complex, functional derivatives remains difficult due to low functional group tolerance, high dilution, extreme reaction conditions, and sometimes low yields using traditional stepwise synthetic methods. “Design of experiments” (DOE) is a method employed for the optimization of reaction conditions, and we showcase this approach to generate a dramatic increase in the yield of specific targets from two different self‐assembling systems. These examples demonstrate that DOE provides an additional tool in tuning self‐assembling, dynamic covalent systems.