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Abstract In this manuscript, the longest O/N and S/N atoms containing heteroacenes (tetraazatetraoxodecacene (TAOD) and tetraazatetrathiodecacene (TATD)) with ten linearly fused rings have been synthesized and fully characterized. The X-ray crystal structures show that O/N atoms containing TAOD exhibits a linear structure, while S/N atoms containing TATD bends in S atom containing heterorings. Obviously, TAOD shows a higher fluorescence quantum yield in solution than that of S atom containing compound TATD. By simple reprecipitation method, TAOD and TATD self-assembly into different microstructures with microwires and microrods, respectively, which demonstrate distinctive non-linear optical properties depending on the orientation of transition dipoles. Graphical abstract Image 1 Highlights • The longest O/N (TAOD) and S/N (TATD) atoms containing heteroacenes with ten linearly fused rings were successfully prepared. • TAOD and TATD show different photophysical and electrochemical properties. • The microcrystals of TAOD and TATD exhibit distinctive non-linear optical properties depending on the orientation of transition dipoles. [ABSTRACT FROM AUTHOR]

Effectively increasing the length of N‐heteroacenes is highly desirable because such materials could have great potential applications in organic optoelectronics. In this review we summarize the recent progress in the construction of larger N‐heteroacenes based on the use of phenazinediamine and its analogues as building blocks to react with different kinds of ortho‐diketones (or tetraketones) or ortho‐dihalides through condensation or coupling reactions. In addition, the potential applications of the corresponding N‐heteroacenes are also presented. [ABSTRACT FROM AUTHOR]