One-pot amination–arylation synthesis and structure–property relationships of luminescent and redox-active aryl-triarylamines and -phenothiazines

Triarylamines and phenothiazines are electron-rich Π-systems and, therefore, as donor components omnipresent in organic electronics, organic photonics, and organic photovoltaics.1 For establishing design principles of donor systems, the interplay between modelling and experimental studies are fruitful, and, therefore, concise access to substance libraries of functional Π-systems by multicomponent reactions2,3 is highly desirable. Employing Pd-catalyzed sequences allows for the efficiently concatening ofelementary steps with a maximum of functional group tolerance in a one-pot fashion.4,5,6 These synthetic methodological advances allow xtensive physical organic structure–property correlations to be established in the electronic ground state (oxidation potential) as well as in the electronic excited state (absorption, emission). Concatenating Suzuki arylation and Buchwald–Hartwig amination in a consecutive three-component fashion7 sets the stage for comprehensive physical–organic correlation studies on the redox, absorption and emission properties of 3,10-diaryl phenothiazines8 and p-,m- and o-aryl triarylamines.9,10

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