Calix[4]arene based selective fluorescent chemosensor for organic acid recognition

Abstract

A novel calix[4]arene-based fluorescent chemosensor bearing a 2-aminopyridine moiety and a naphthalenic fluorophore was synthesized The chemical structure of the product was elucidated by FT-IR, MS-FAB, NMR and elemental analyses. Then, the properties and identification mechanism of the synthesized chemosensor were investigated. The results show that the chemosensor exhibits selective fluorescent quenching in the presence of aromatic organic acid in acetonitrile solution, and that the binding ability of the chemosensor with organic acid is in the order of p-cyanic-benzyl acid > p-chloric-benzyl acid > p-methoxyl-benzyl acid > benzyl acid.

References

1. Steed J W Atwood J L Supramolecular chemistryChichesterJohnWiley and Sons Ltd 2000
2. Schneider H J Yatsimirsky A Principles and methods in supramolecularchemistryChichesterJohn Wiley and Sons Ltd 2000
3. Desvergne J P Czarnik A W Chemosensors of ion and moleculerecognitionDordrechtNATO ASI Series, Kluwer Academic 1997
4. Czarnik A W FluorescentChemosensors for Ion and Molecule Recognition. ACS Symposium SeriesNo538WashingtonAmerican Chemical Society 1992
5. Zhang M Q Shen H F Yang Z R Chen H Q Wong K Y Development of oxygen sensor based on luminescencequenching (I) -Synthesis and Selection of IndicatorsJournal of South China University of Technology: Natural ScienceEdition 2001 29(1)5155(in Chinese)
6. Ikeda A Shinkai S Novel cavity design using calix[n] arene skeletons: Toward molecular recognition and metal bindingChem Rev 1997 97(5)17131734. doi:10.1021/cr960385x
7. Goswami S Ghosh K Dasgupta S Troger's base molecular scaffolds in dicarboxylic acidrecognitionJ Org Chem 2000 65(7)19071914. doi:10.1021/jo9909204
8. Benito H M Gomez-Garcia M Jimenez Blanco J L Ortiz Mellet C Garcia Fernandez JM Carbohydrate -basedreceptors with multiple thiourea binding sites: Multipoint hydrogenbond recognition of dicarboxylates and monosaccharidesJ Org Chem 2001 66(4)13661369. doi:10.1021/jo001508n
9. Watanabe S Higashi N Kobayashi M Hamanaka K Takata Y Yoshida K Stereoselectiveoptical sensing of dicarboxylate anions by an inducedfit type Ru (II)receptorTetrahedron Lett 2000 41(21)45834586. doi:10.1016/S0040‐4039(00)00635‐3
10. Carr J D Coles S J Hursthouse M B Light M E James H R Westwood T J Redoxswitchedcontrol of binding strength in hydrogen-bonded metallocene complexesAngew Chem Int Ed Engl 2000 39(18)32963299. doi:10.1002/1521‐3773(20000915)39:18<3296::AID‐ANIE3296>3.0.CO;2‐U
11. Albert J S Goodman M S Hamilton A D Molecular recognition of proteins: Sequence-selective bindingof aspartate pairs in helical pep tidesJ Am Chem Soc 1995 117(3)11431144. doi:10.1021/ja00108a037
12. Lakowicz J R Principles of fluorescence spectroscopy. 2^nd ed.New YorkKluwerA cademico Plenum Publishers 1999
13. Jaime C De Mendoza Javier Prados P Nieto P M Sanchez C Carbon-¹³NMRchemical shifts: a single rule to determine the conformation of calix[4]arenesJ Org Chem 1991 56(10)33723376. doi:10.1021/jo00010a036
14. Matsumoto H Shinkai S Metal-induced conformationalchange in pyrene-appended calix[4] crown-4 which is useful for metalsensing and guest tweezingTetrahedron Lett 1996 37(1)7780. doi:10.1016/0040‐4039(95)02106‐X
15. Krauss R Weinig H G Seydack M Bendig J Koert U Molecular signal transduction through conformationaltransmission of a perhydroanthracene transducerAngew Chem Int Ed 2000 39(10)18351837. doi:10.1002/(SICI)1521‐3773(20000515)39:10<1835::AID‐ANIE1835>3.0.CO;2‐S