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Enhanced Charge Transfer Aptitude Resulting in Remarkable Chromogenic F‐ Sensing in a Naphthalene‐Benzocaine Platform by Simple Atomic Substitution: Azo Dye versus Schiff‐Base
Author(s) -
Bhattacharyya Arghyadeep,
Makhal Subhash Chandra,
Ghosh Soumen,
Guchhait Nikhil
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702467
Subject(s) - chromogenic , schiff base , chemistry , benzocaine , intramolecular force , base (topology) , naphthalene , photochemistry , polymer chemistry , organic chemistry , chromatography , mathematical analysis , mathematics , immunology , biology
We hereby report two compounds, (E)‐1‐(2‐(4) phenyldiazenyl) naphthalen‐2‐ol ( AD ) and (E)‐ethyl 4‐((2‐hydroxynaphthalen‐1yl) methyleneamino) benzoate ( SB ) and compared their respective responses towards F − ion. AD being an azo dye acts as a chromogenic sensor for F − and displays a color change from yellow to purple and can also detect F − in a mixture of anions. On the other hand, SB (a Schiff base) shows a deepening of its already existing yellow color in presence of F − but in presence of mixture of anions the response is very poor. The theoretically optimized structural analyses of AD and SB show that the extended intramolecular charge transfer (ICT) present in AD is accountable for the successful sensing of F − . The limits of detection for SB and AD were calculated to be 483 ppb and 18.3 ppb respectively. Thus, by simple manipulation of a functional group an efficient chromogenic F − sensor could be constructed, thereby establishing the superiority of azo dye over Schiff base as far as Fluoride sensing is concerned.