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Synthesis of sterically hindered antipyrines for intramolecular charge transfer facilitated sensing
Author(s) -
Bian Linyi,
Sun Gang,
Sun Yuxi,
Tang Weihua
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.2948
Subject(s) - chemistry , steric effects , moiety , photochemistry , quantum yield , fluorescence , phenothiazine , intramolecular force , conjugated system , carbazole , electron transfer , electrochemistry , yield (engineering) , combinatorial chemistry , organic chemistry , polymer , medicine , physics , materials science , electrode , quantum mechanics , metallurgy , pharmacology
A new series of sterically hindered antipyrine derivatives have been synthesized by Schiff base condensation for potential fluorescence sensing applications. Their optical, thermal, and electrochemical properties were fully characterized. Broad absorption spectra were observed as a result of the strong intramolecular charge transfer between antipyrine and sterically hindered conjugated moiety. Reversible one electron oxidation couple was observed for most compounds, with carbazole, phenothiazine, and bithiophene functionalized derivatives exhibiting extra reversible one one‐electron oxidation process at higher positive potentials. Cabazole functionalized antipyrine derivative APCZ presents good fluorescence sensing for Co 2+ and Cu 2+ , with 3.41‐fold enhancement in fluorescence intensity and 2‐fold enhancement in fluorescence quantum yield observed. Copyright © 2012 John Wiley & Sons, Ltd.