A fluorescent probe based on tetrahydro[5]helicene for highly selective recognition of hydrogen sulfide

作者:Lei, Yang; Wang, Kun-Peng*; Chen, Shaojin; Zhang, Qi; Hu, Zhi-Qiang*
来源:Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2018, 204: 295-300.
DOI:10.1016/j.saa.2018.06.066

摘要

Endogenous hydrogen sulfide plays an important role in various physiological and pathological processes and the convenient and selective recognition of hydrogen sulfide has become a research hotspot. We designed and synthesized a tetrahydro[5]helicene and 2,4-dinitrobenzene conjugate (HD-DNP) as an effective fluorescent probe for selective detection of H2S. The selective deprotection of 2,4-dinitrophenyl ether group of HD-DNP by H2S led to a dramatic fluorescent enhancement (101-fold) at 500 nm and colorimetric change in DMSO-PBS solution. HD-DNP displays many advantages including low background without any self-fluorescence, as well as high selectivity towards common bio-thiols such as Cysteine, Homocysteine and Glutathione. The detection limit of this probe for H2S was found to be about 2.4 mu M with a wide linear range (10-70 mu M). The response mechanism of the probe with HS- is confirmed to be thiolysis of the dinitrophenyl ether induced by HS- through H-1 NMR comparison investigations.