Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

Abstract

The first series of discrete multichromophore arrays of dibenzotetraaza[14]annulene (DBTAA), containing flexible bridges, have been synthesized in 40–46% isolated yields. The key asymmetrical intermediates, carrying two distinctly addressable functionalities (ROH vs. ROCH₂–CC–H and R(CH₂)_nBr vs. ROCH₂–CC–H) at the macrocycle periphery, were synthesized in moderate to high (30–78%) isolated yields. Facile synthetic protocols developed for the synthesis of discrete DBTAA arrays offer several advantages such as operational simplicity and easy post-synthetic workup that overcome the need for laborious chromatographic purification. All new compounds were characterized by microanalysis, mass spectrometry, UV-Vis, FTIR-ATR, and ¹H and ¹³C NMR spectroscopy. Structural features were briefly discussed with emphasis on several potential applications.