Completely o-Phenylene Bridged N 4-Cyclophane: A Missing Link in the Phenylene Bridge N 4-Cyclophane Family

Unprecedented types of metal-free complete o-phenylenebridged N (4)-cyclophanes (M1 and M2) have been synthesized via sequential palladium-catalyzedBuchwald-Hartwig N-arylation reactions. Thesecyclophanes may be considered as aromatic analogues of aliphatic group-spaced N (4)-macrocycles. These have been characterizedfully using physicochemical characterization techniques and finallyby single crystal X-ray structure determination. Their redox and spectralproperties have been characterized by cyclic voltammetry, UV-visspectro-electrochemistry, fluorescence spectral studies, and DFT calculations.These studies have shown rich redox, spectral, and photophysical propertiesthat could make both M1 and M2 potentialcandidates for various applications.

Automated summary

Unprecedented metal-free complete o-phenylenebridged N (4)-cyclophanes (M1 and M2) were synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions. These cyclophanes can be considered as aromatic analogues of aliphatic group-spaced N (4)-macrocycles. Physicochemical characterization techniques and single crystal X-ray structure determination were used to fully characterize them. Their redox and spectral properties were characterized by cyclic voltammetry, UV-vis spectro-electrochemistry, fluorescence spectral studies, and DFT calculations. These studies revealed rich redox, spectral, and photophysical properties, making both M1 and M2 potential candidates for various applications.