Abstract
A series of 2-(N-oxide pyridyl)-5-methoxythiazoles were synthesized and corresponding optical properties were also investigated. It is first found that a digital-type fluorescent responses in a sharp pH variation with dual-emission could be fulfilled based on a small fluorophore.
References
de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566
Basabe-Desmonts L, Reinhoudt DV, Crego-Calama M (2007) Design of fluorescent materials for chemical sensing. Chem Soc Rev 36:993–1017
Gonçalves MST (2009) Fluorescent labeling of biomolecules with organic probes. Chem Rev 109:190–212
Szacilowski K (2008) Digital information processing in molecular systems. Chem Rev 108:3481–3548
Valuer B (2002) Molecular fluorescence: principles and applications. Wiley-VCH, Weinheim
Safavi A, Abdollahi (1998) Optical sensor for high pH values. Anal Chim Acta 367:167–173
Gunnlaugsson T, Leonard JP, Sénéchal K, Harte AJ (2003) pH Responsive Eu(III)-phenanthroline supramolecular conjugate: novel “off-on-off” luminescent signaling in the physiological pH range. J Am Chem Soc 125:12062–12063
Charier S, Ruel O, Baudin JB, Alcor D, Allemand JF, Meglio A, Jullien L (2004) An efficient fluorescent probe for ratiometric pH measurements in aqueous solutions. Angew Chem Int Ed 43:4785–4788
Gabor G, Walt DR (1991) Sensitivity enhancement of fluorescent pH indicators by inner filter effects. Anal Chem 63:793–796
Riddle JA, Jiang X, Huffman J, Lee D (2007) Siganl-amplifying resonace energy transfer: a dynamic multichromophore array for allosteric switching. Angew Chem Int Ed 46:7019–7122
Uchiyama S, Makino Y (2009) Digital fluorescent pH sensors. Chem Comm 2646–2648
Zheng MH, Jin JY, Sun W, Yan C-H (2006) A new series of fluorescent 5-methoxy-2-pyridylthiazoles with a pH-sensitive dual-emission. New J Chem 30:1192–1196
Chmurzyński L, Liwo A, Barczyński P (1996) A potentiometric study of acid–base equilibria of substituted pyridine N-oxides in nitrobenzene. Anal Chim Acta 335:147–153
Abraham MH, Honcharova L, Rocco SA, Acee WE Jr, De Fina KM (2011) The lipophilicity and hydrogen bond strength of pyridine-N-oxides and protonated pyridine-N-oxides. New J Chem 35:930–936
Acknowledgments
M.-H. Zheng thanks the financial supports from Yanbian University.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOC 531 kb)
Rights and permissions
About this article
Cite this article
Zheng, MH., Zhang, MM., Li, HH. et al. Digital pH Fluorescent Sensing Shown by Small Organic Molecules. J Fluoresc 22, 1421–1424 (2012). https://doi.org/10.1007/s10895-012-1095-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-012-1095-4