A concentration dependent auto-relay-recognition by the same analyte: a dual fluorescence switch-on by hydrogen sulfide via Michael addition followed by reduction and staining for bio-activity.
H2S is shown, for the first time, to play an extraordinary dual role due to its nucleophilicity and reducing property with our single chemosensor, PND [4-(piperidin-1-yl) naphthalene-1,2-dione]. The initial nucleophilic attack via Michael addition (a lower concentration of H2S, blue fluorescence) is followed by the reduction of the 1,2-diketo functionality (a higher concentration of H2S, green fluorescence). This chemosensor, which also shows biological response, is remarkably effective in sensing the same analyte (H2S) at its different concentrations in a relay pathway via a fluorescence "off-on-on" mechanism, and this is also supported by DFT calculation and Cyclic voltammograms.
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, West Bengal, India. spgoswamical@yahoo.com.
Avijit Kumar
AK
Das
Shyamaprosad
S
Goswami
Gorachand
G
Dutta
Sibaprasad
S
Maity
Tarun Kanti
TK
Mandal
Kalyani
K
Khanra
Nandan
N
Bhattacharyya
D055664:Electrochemical Techniques; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D006862:Hydrogen Sulfide / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D011789:Quantum Theory
C000609229:4-(piperidin-1-yl)naphthalene-1,2-dione; D005456:Fluorescent Dyes; D009281:Naphthalenes; D006862:Hydrogen Sulfide