Format

Send to

Choose Destination
See comment in PubMed Commons below
Talanta. 2012 Oct 15;100:229-38. doi: 10.1016/j.talanta.2012.08.008. Epub 2012 Aug 17.

Synthesis, characterization of conjugated oligo-phenylene-ethynylenes and their supramolecular interaction with β-cyclodextrin for salicylaldehyde detection.

Author information

1
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education, China), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China. liu_meiling@126.com

Abstract

Four new conjugated oligo-phenylene-ethynylenes derivatives, N-methyl-4-(4-acetylthiophenylethynyl)-1,8-naphthalimide (1), thioacetic acid S-[4-(4-aminophenyl-ethynyl)phenyl]ester (2), 4-methylthiophenylethynylbenzenamine (3), N-methyl-4-(4-methyl-thiophenyl-ethynyl)-1,8-naphthalimide (4), were synthesized by Sonogashira and Eglinton cross-coupling reactions. The structures of the four compounds were confirmed by (1)HNMR, (13)CNMR, MS and IR and their spectral characteristics were studied by ultraviolet and visible (UV) spectroscopy as well as fluorescence spectroscopy in different medium. It was found that the fluorescence properties of compounds 2 and 3 were notably improved in aqueous solutions in the presence of β-cyclodextrin (β-CD). Spectral analysis supported the suppositions that the fluorescence intensity enhancement was due to the formation of inclusion complex with β-CD. The supramolecular interaction was investigated in detail and the reaction mechanism was provided. A salicylaldehyde determination method in aqueous medium was established based on the supramolecular complex of compound 3. Under the optimum conditions, the supramolecular complex exhibited a dynamic fluorescence response range for salicylaldehyde from 0.6 to 240×10(-6) molL(-1), with a detection limit of 1×10(-8) molL(-1).

PMID:
23141331
DOI:
10.1016/j.talanta.2012.08.008
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Elsevier Science
    Loading ...
    Support Center