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Acid–Base Sensors Based on Novel Quinone‐Type Dyes
Author(s) -
Elhabiri Mourad,
Siri Olivier,
SornosaTent Alejandra,
AlbrechtGary AnneMarie,
Braunstein Pierre
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305206
Subject(s) - protonation , antiaromaticity , cyanine , chemistry , chromophore , molecule , potentiometric titration , quinone , conjugated system , photochemistry , absorption (acoustics) , combinatorial chemistry , stereochemistry , electrode , materials science , organic chemistry , polymer , fluorescence , ion , aromaticity , physics , quantum mechanics , composite material
We present a detailed study on the acid–base behaviour of a family of “potentially antiaromatic” p ‐benzoquinonediimine ligands. These 12π electron molecules can be considered as constituted of two chemically connected but electronically not conjugated 6π‐electron subunits. Upon successive protonation, “mono” and “double” cyanine‐type chromophores are generated in solution and allow a precise and sensitive spectrophotometric detection. These molecules represent a new class of tunable quinones whose electronic and structural properties can be triggered by proton input, as established by a complete physico‐chemical study involving a combination of potentiometric and spectrophotometric methods (absorption and emission).