We herein describe a new design principle to achieve B/N‐doped cyclophane where an electron‐donor block of three triarylamines (Ar3N) and an acceptor block of three triarylboranes (Ar3B) are spatially separated on opposite sides of the π‐extended ring system. DFT computations revealed the distinct electronic structure of the
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Abstract block ‐type macrocycleMC‐ b ‐B3N3 with a greatly enhanced dipole moment and reduced HOMO–LUMO energy gap in comparison to its analogue with alternating B and N sites,MC‐ alt ‐B3N3 . The unique arrangement of borane acceptor Ar3B and amine donor Ar3N components inMC‐ b ‐B3N3 induces exceptionally strong intramolecular charge transfer in the excited state, which is reflected in a largely red‐shifted luminescence at 612 nm in solution. The respective linear open‐chain oligomerL‐ b ‐B3N3 was also synthesized for comparison. Our new approach to donor–acceptor macrocycles offers important fundamental insights and opens up a new avenue to unique optoelectronic materials. -
Li, Pengfei ; Shimoyama, Daisuke ; Zhang, Niu ; Jia, Yawei ; Hu, Guofei ; Li, Chenglong ; Yin, Xiaodong ; Wang, Nan ; Jäkle, Frieder ; Chen, Pangkuan ( , Angewandte Chemie)
Abstract We herein describe a new design principle to achieve B/N‐doped cyclophane where an electron‐donor block of three triarylamines (Ar3N) and an acceptor block of three triarylboranes (Ar3B) are spatially separated on opposite sides of the π‐extended ring system. DFT computations revealed the distinct electronic structure of the
block ‐type macrocycleMC‐ b ‐B3N3 with a greatly enhanced dipole moment and reduced HOMO–LUMO energy gap in comparison to its analogue with alternating B and N sites,MC‐ alt ‐B3N3 . The unique arrangement of borane acceptor Ar3B and amine donor Ar3N components inMC‐ b ‐B3N3 induces exceptionally strong intramolecular charge transfer in the excited state, which is reflected in a largely red‐shifted luminescence at 612 nm in solution. The respective linear open‐chain oligomerL‐ b ‐B3N3 was also synthesized for comparison. Our new approach to donor–acceptor macrocycles offers important fundamental insights and opens up a new avenue to unique optoelectronic materials.