ol8b01190_si_001.pdf (4.18 MB)
Synthesis of Cyclobutadienoid-Fused Phenazines with Strongly Modulated Degrees of Antiaromaticity
journal contribution
posted on 2018-05-18, 21:29 authored by Yew Chin Teo, Zexin Jin, Yan XiaThe streamlined synthesis
of a series of regioisomeric azaacene
analogues containing fused phenazine and antiaromatic cyclobutadienoids
(CBDs), using a catalytic arene–oxanorbornene annulation, followed
by aromatization is reported. Controlling the fusion patterns allowed
strong modulation of local antiaromaticity. Enhancing antiaromaticity
in these regioisomeric azaacenes led to stabilized LUMO, reduced band
gap, and quenched fluorescence. This synthetic strategy provides a
facile means to fuse CBDs with variable degrees of antiaromaticity
onto N-heteroarenes to tune their optoelectronic
properties.