Synthesis of azobenzene containing macrocycles

Hoşgör, Ege
Aromatic azo compounds are one of the well-known research topics of recent times due to their photoisomeric properties under ultraviolet or visible light. Generally, these substances undergo isomerization from the thermodynamically more stable trans isomer to the cis isomer when irradiated with appropriate light radiation. The incorporation of azo groups to the macrocycle skeleton is an important part of the supramolecular chemistry. Azobenzene photoisomerization is the key mechanism of molecular motors that can be controlled by light. These are further proposed to act as catch and release receptors. In this study, macrocycles were constructed from 2-aminobenzoic acid. The benzoic acids were linked together with ethylene glycol units through ester linkage (diethylene glycol, triethylene glycol, tetraethylene glycol). Then, the amino parts were converted to azo linkage with Pb(OAc)4. Moreover, L-phenylalanine was incorporated into these macrocycles to get chiral macrocycles. The photophysical and photochemical properties of these macrocycles were investigated both experimentally and theoretically.


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Citation Formats
E. Hoşgör, “Synthesis of azobenzene containing macrocycles,” M.S. - Master of Science, Middle East Technical University, 2021.