Design and synthesis of a Cu(II)-complex-based carbazole-hemicyanine hybrid for fluorescent sensing of H2S in SDS micellar solution

A novel fluorescent chemosensor HACBA with carbazole-hemicyanine fluorophore as signal reporter and N,N,N'-tri(2-pyridylmethyl)ethylenediamine (TPEA) as binding sites was designed and synthesized. Its assemblies with anionic surfactant sodium dodecyl sulfate (SDS) show improved fluorescence emission stability and enhanced fluorescence intensity. HACBA/SDS system can selectively recognize Cu2+, which led to a dramatic fluorescence quenching. The in situ resultant HACBA-Cu(II)/SDS ensemble functioned as a highly selective and sensitive sensor for H2S with a turn-on fluorescent response. Our results show that the “on-off-on” molecular switch occured through the reversible formation-dissociation reaction between HACBA-Cu(II) complex and HACBA/CuS in the SDS micellar solution, and at least 3 cycles of on-off-on switches were observed.

Graphical abstractA novel carbazole-hemicyanine hybrid based “on-off-on” molecular switch (HACBA) was designed and synthesized. The surfactant-assisted HACBA-Cu(II)/SDS ensemble were successfully used for selective sensing of H2S.Download high-res image (183KB)Download full-size image