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Design, Synthesis and Photochemical Properties of a Phenalenone‐Based pH Sensor: Switchable pH Sensing in Four Detectable Channels
Author(s) -
Mitra Amritaa,
Bose Suranjana,
Biswas Sachidulal,
Bandyopadhyay Pinaki,
Sarkar Arindam
Publication year - 2018
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800420
Subject(s) - chemistry , ph indicator , photoinduced electron transfer , photoluminescence , molecule , analytical chemistry (journal) , photochemistry , combinatorial chemistry , electron transfer , optoelectronics , chromatography , materials science , organic chemistry
The synthesis and pH‐sensing property of a novel phenalenone‐based compound, 9‐(4‐hydroxyphenylamino)‐1‐oxo‐phenalenone (HPAP), is reported. The newly synthesized compound is capable of functioning as a pH sensor in the region of pH 7 to 12. The sensor can be used as a colorimetric indicator in the transition from pH 10 to pH 11. The sensor is able to function in four detectable channels. All four channels (UV, emission, colorimetric/visible and photoluminescence) have been shown to be reversible, thus implying the reuse of this single‐molecule sensor and indicator for several experiments. Mechanistic investigations have been performed by UV, NMR and DFT studies which indicate that a photoinduced electron transfer (PET) based mechanism could be operative. Straightforward and cost‐effective application of the sensor in thin‐layer chromatography has also been established.