Two
fully fused acceptor–donor–acceptor (A–D–A)
architecture conjugated derivatives (NPF and NCF) comprising an electron-withdrawing naphthalimide (NMI) and two
different electron-donating cores, phenanthrene and carbazole, respectively,
were conveniently synthesized by bismuth(III)-catalyzed selective
cyclization of vinyl ethers. Compared with their corresponding single
bond-linked A–D–A molecules NPS and NCS, both having a moderately twisted aromatic configuration,
the ring fusion strategy leads to fully coplanar conjugated skeletons
and greatly changes the electronic structures, photophysical properties,
self-assembling behaviors, and molecular packing motifs. In particular,
the naphthalimide/carbazole derivative NCF exhibits intriguing
2D brickwork packing and significantly enhanced self-assembling properties.