Borylated Arylamine–Benzothiadiazole Donor–Acceptor Materials as Low-LUMO, Low-Band-Gap Chromophores

Fused and ladder-type benzothiadiazole–arylamine
donor–acceptor
C,N-chelated boron complexes were synthesized through direct electrophilic
C–H borylation. The frontier molecular orbital energy levels
of the borylated materials then could be modulated through variation
of the exocyclic boron substituents by transmetalation with different
diarylzinc reagents. The borylated materials possessed low band gaps
and low LUMO energy levels with a number of examples also showing
significant absorbance at >700 nm; however, low photoluminescence
quantum yields were found for all these borylated compounds.

通过直接亲电C-H硼化反应合成了融合型及梯型苯并噻二唑-芳胺供体-受体C,N-螯合硼配合物。通过使用不同的双芳基锌试剂进行转金属化，可调节硼化材料的 frontier 分子轨道能级，从而改变外环硼取代基。这些硼化材料具有低带隙和低LUMO能级，其中许多实例在700 nm以上显示出显著的吸收率；然而，所有这些硼化化合物的光致发光量子产率均较低。