Experimental and theoretical investigations of acid sensing properties of pyrazino[2,3-g]quinoxaline derivatives

•Pyrazino[2,3-g]quinoxaline (PQ8) derivative that sense the acid in trace (ppb) levels has been designed.•The sensing behavior was visually perceivable and reversible both in solution and solid state.•The intermolecular FRET that occurs from PQ8 to the protonated PQ8 leads to the quenching of fluore...

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Bibliographic Details
Published in:Journal of molecular structure 2021-02, Vol.1225, p.129120, Article 129120
Main Authors: Vishwakarma, Vinod Kumar, Adupa, Vasista, Anki Reddy, K., Ammathnadu Sudhakar, Achalkumar
Format: Article
Language:English
Subjects:
Acidochromism
Chemosensor
Donor-acceptor
FRET
Pyrazino[2,3-g]quinoxaline
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Summary:•Pyrazino[2,3-g]quinoxaline (PQ8) derivative that sense the acid in trace (ppb) levels has been designed.•The sensing behavior was visually perceivable and reversible both in solution and solid state.•The intermolecular FRET that occurs from PQ8 to the protonated PQ8 leads to the quenching of fluorescence in response to the acid. We report the ability of a pyrazino[2,3-g]quinoxaline derivative substituted with eight peripheral flexible n-octyloxy chains, to sense the volatile trifluoroacetic acid in trace amounts (in parts per billion levels). The reversible detection of acid sensing behavior was visually perceivable in both solution as well as in the drop-casted film on a TLC paper based strip. Density functional theory studies were carried out to elucidate the mechanism of the sensing behavior. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2020.129120