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New fluorescent bis‐β‐cyclodextrin‐indolizine sensor. Synthesis and sensing ability
Author(s) -
Surpateanu Georgiana G.,
Landy David,
Lungu Neculai C.,
Fourmentin Sophie,
Surpateanu Gheorghe
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440405
Subject(s) - indolizine , chemistry , cyclodextrin , fluorescence , dimer , pyridine , monomer , fluorescence spectroscopy , phenol , combinatorial chemistry , photochemistry , medicinal chemistry , organic chemistry , polymer , physics , quantum mechanics
The synthesis of 1,3‐[bis‐ N ‐6A‐deoxy‐β‐cyclodextrin‐6A‐yl‐aminocabonyl]‐7‐pyridin‐4‐yl indolizine is reported. The reaction proceeds by an amidation between 6‐amino‐β‐cyclodextrin and 1,3‐[bis‐(‐4‐nitrophenoxycarbonyl)‐7‐[pyridine‐4‐yl)] and yields the first sensor having in its structure the fluorescent indolizine and two β‐cyclodextrin fragments. The sensing ability towards phenol, p ‐cresol and adamantan‐1‐ol has been evaluated by fluorescence spectroscopy. The molecular modelling study realised by MM3 and AM1 methods shows that non cooperative conformations are favoured, thus explaining that inclusion ability is not increased by such dimer, and that sensitivity is not enhanced as compared to corresponding monomeric sensors.