Synthesis and application of ratiometric and "turn-on" fluorescent pH sensors: An advanced organic undergraduate laboratory

Journal of Chemical Education

Volumn 91, Issue 11, 2014, Pages 1990-1994

  Hutt, Johnathon T ^a   Aron, Zachary D ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Aldehydes Ketones; Dyes Pigments; Fluorescence Spectroscopy; Hands On Learning Manipulatives; Heterocycles; Interdisciplinary Multidisciplinary; Organic Chemistry; pH; Precipitation Solubility; Upper Division Undergraduate

Indexed keywords

EID: 84922438968     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed4006166     Document Type: Article

References (16)

1. Fukaminato, T. Single-Molecule Fluorescence Photoswitching: Design and Synthesis of Photoswitchable Fluorescent Molecules J. Photochem. Photobiol. C 2011, 12 (3) 177-208
2. de Silva, A. P.; Moody, T. S.; Wright, G. D. Fluorescent PET (Photoinduced Electron Transfer) Sensors As Potent Analytical Tools Analyst 2009, 134 (12) 2385-2393
3. 2-pyrazolines: Synthesis, X-ray Structure, Photophysics, And Cation Complexation Properties J. Phys. Chem. A 2000, 104 (26) 6171-6188
4. Domaille, D. W.; Que, E. L.; Chang, J. C. Synthetic Fluorescent Sensors for Studying the Cell Biology of Metals Nat. Chem. Biol. 2008, 4 (3) 168-175
5. Ho, M. H.; Balaganesan, B.; Chen, C. H. Blue Fluorescence and Bipolar Transport Materials Based on Anthracene and Their Application in OLEDs Isr. J. Chem. 2012, 52 (6) 484-495
6. Deibler, K.; Basu, P. Continuing Issues with Lead: Recent Advances in Detection Eur. J. Inorg. Chem. 2013, 2013 (7) 1086-1096
7. Hancock, R. D. The Pyridyl Group in Ligand Design for Selective Metal Ion Complexation and Sensing Chem. Soc. Rev. 2013, 42 (24) 1500-1524
8. Yuab, L.; Lin, W.; Zheng, K.; He, L.; Huang, W. Far-Red to near Infrared Analyte-Responsive Fluorescent Probes Based on Organic Fluorophore Platforms for Fluorescent Imaging Chem. Soc. Rev. 2013, 42 (2) 622-661
9. Patterson, A. L.; May, M. D.; Visser, B. J.; Kislukhin, A. A.; Vosburg, D. V. Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories J. Chem. Educ. 2013, 90 (12) 1685-1687
10. Miller, T. A.; Spangler, M.; Burdette, S. C. Lighting Up Protons with MorphFl, a Fluorescein-Morpholine Dye: An Experiment for the Organic Laboratory J. Chem. Educ. 2011, 86 (11) 1569-1573
11. 2+: An Introduction to Polymers and Chemical Sensing J. Chem. Educ. 2005, 82 (9) 1370-1371
12. Valeur, B.; Leray, I. Design Principles of Fluorescent Molecular Sensors for Cation Recognition Coord. Chem. Rev. 2000, 205 (1) 3-40
13. de Silva, A. P.; Nimal Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling Recognition Events with Fluorescent Sensors and Switches Chem. Rev. 1997, 97 (5) 1515-1566
14. Demchenko, A. Introduction to Fluorescence Sensing; Springer: New York, 2009; pp 250-258.
15. Hutt, J. T.; Aron, Z. D. Efficient, Single-Step Access to Imidazo[1,5- a ]pyridine N -Heterocyclic Carbene Precursors Org. Lett. 2011, 13 (19) 5256-5259
16. Hutt, J. T.; Jo, J.; Chen, C.-H.; Lee, D.; Aron, Z. D. Fluorescence Switching of Imidazo[1,5- a ]pyridinium Ions: pH-Sensors with Dual Emission Pathways Org. Lett. 2012, 14 (12) 3162-3165