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Triphenylamine‐Based Pyridine N ‐Oxide and Pyridinium Salts for Size‐Selective Recognition of Dicarboxylates
Author(s) -
Ghosh Kumaresh,
Masanta Goutam,
Chattopadhyay Asoke P.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900471
Subject(s) - triphenylamine , chemistry , pyridinium , pyridine , binding constant , selectivity , quenching (fluorescence) , photochemistry , pyridinium compounds , fluorescence , stereochemistry , binding site , medicinal chemistry , organic chemistry , biochemistry , physics , quantum mechanics , catalysis
Triphenylamine‐based receptors 1 – 3 have been designed and synthesized for the recognition of dicarboxylates. The correct dispositions of the binding groups in both 1 and 2 under 4,4′‐dicarbonyltriphenylamine spacer enable them to bind aliphatic dicarboxylates of different chain lengths with moderate binding constant values. In the binding event, triphenylamine‐based pyridinium salt 2 is found to be more effective than triphenylamine‐based pyridine N ‐oxide 1 and shows selectivity for long‐chain pimelate. Binding takes place at charged sites with concomitant PET‐based (photo‐induced electron transfer) quenching of emission of triphenylamine motif. The binding was monitored in DMSO using 1 H NMR, UV/Vis and fluorescence spectroscopic methods. Efficiency of pyridinium binding site over the others in the present study has been rationalised by invoking theoretical results. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)