Abstract
The solvatochromic 9-hydroxybenzo[b]quinolizinium ion is shown to operate as fluorescent probe for the detection of water in acetonitrile. The dual fluorescence of this photoacid and its dependence on the content of water in the medium enable the ratiometric analysis of the fluorescence data.
References
Fischer K (1935) Wasserbestimmung. Angew Chemie 48:394–396. doi:10.1002/ange.19350482605
O'Keefe WK, Ng FTT (2008) Validation of a gas chromatography/thermal conductivity detection method for the determination of the water content of oxygenated solvents. J Chromatogr A 1182:113–118. doi:10.1016/j.chroma.2007.12.044
Minamihashi K, Kuniyoshi Y, Hisamoto H, Sasaki S, Suzuki K (2001) Optical determination of low-level water concentrations in organic solvents using fluorescent acridinyl dyes and dye-immobilized polymer membranes. Anal Chem 73:5339–5345. doi:10.1021/ac010535q
Tran CD, Grishko VI (2004) Determination of water contents in leaves by a near-infrared multispectral imaging technique. Microchem J 76:91–94. doi:10.1016/j.microc.2003.10.015
Niu CG, Guan AL, Zeng GM, Liu YG, Li ZW (2006) Fluorescence water sensor based on covalent immobilization of chalcone derivative. Anal Chim Acta 577:264–270. doi:10.1016/j.aca.2006.06.046
Gruda I, Bolduc F (1984) Spectral properties and basicity of Stilbazolium Betaines containing bulky substituents on the Quinoid ring. J Org Chem 49:3300–3305. doi:10.1021/jo00192a010
Liu WH, Wang Y, Jin WJ, Shen GL, Yu RQ (1999) Solvatochromogenic flavone dyes for the detection of water in acetone. Anal Chim Acta 383:299–307. doi:10.1016/S0003-2670(98)00789-2
Gao F, Luo FB, Chen XX, Yao W, Yin J, Yao Z, Wang L (2009) Fluorometric determination of water in organic solvents using europium ion-based luminescent nanospheres. Microchim Acta 166:163–167. doi:10.1007/s00604-009-0180-0
Kim JS, Choi MG, Huh Y, Kim MH, Kim SH, Wang SY, Chang SK (2006) Determination of water content in aprotic organic solvents using 8-hydroxyquinoline based fluorescent probe. Bull Korean Chem Soc 27:2058–2060 doi does not exist
Park H, Chang SK (2015) Signaling of water content in organic solvents by solvatochromism of a hydroxynaphthalimide-based merocyanine dye. Dyes Pigm 122:324–330. doi:10.1016/j.dyepig.2015.07.010
Choi MG, Kim MH, Kim HJ, Park JE, Chang SK (2007) A simple ratiometric probe system for the determination of water content in organic solvents. Bull Kor Chem Soc 28:1818–1820
Men GW, Chen CR, Liang CS, Han WK, Jiang SM (2015) A novel cascade strategy with supramolecular and chemodosimetric methods for designing a fluorescent ratiometric detector hypersensitive to trace water. Analyst 140:5454–5458. doi:10.1039/c5an00917k
Granzhan A, Ihmels H, Tian M (2015) The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes. ARKIVOC:494–523. doi:10.3998/ark.5550190.p009.339
Schäfer K, Ihmels H, Bohne C, Valente KP, Granzhan A (2016) Hydroxybenzo[b]quinolizinium ions: water-soluble and Solvatochromic Photoacids. J Org Chem 81:10942–10954. doi:10.1021/acs.joc.6b01991
Ihmels H, Schafer K (2009) Excited-state acidity of the 8-hydroxyacridizinium ion-a water-soluble photoacid. Photochem Photobiol Sci 8:309–311. doi:10.1039/b816048a
Sukunza D, Cuadro AM, Alvarez-Builla J, Vaquero JJ (2016) Recent advances in the Synthesis of Azonia aromatic Heterocycles. J Org Chem 81:10126–10135. doi:10.1021/acs.joc.6b01092
Vaquero JJ, Alvarez-Builla J, Barluenga J (2011) Modern Heterocyclic Chemistry. Wiley-VCH, Weinheim, p 1989
Ihmels H (2011) In: Thomas J (ed) Science of Synthesis, vol 15. Georg Thieme Verlag, Stuttgart, p 75
Ihmels H (2004) In: Black D (ed) Science of Synthesis, vol 15. Georg Thieme Verlag, Stuttgart, p 907
Earley WG, Kumar V, Mallamo JP, Subramanyam C, Dority JA, Miller MS, Dehavenhudkins DL, Aimone LD, Kelly MD, Ault B (1995) Novel Benzo[b]Quinolizinium Cations as uncompetitive N-methyl-D-aspartic acid (Nmda) antagonists - the relationship between log-D and agonist independent (closed) Nmda Channel block. J Med Chem 38:3586–3592. doi:10.1021/Jm00018a018
Acknowledgements
Generous support by the Deutsche Forschungsgemeinschaft (IH24/10-1) is gratefully acknowledged. We thank Ms. Ulrike Koch, Ms. Sandra Uebach, and Ms. Alessa Schneider, University of Siegen, resp., for technical assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Schäfer, K., Ihmels, H. Ratiometric Detection of Water in Acetonitrile with 9-Hydroxybenzo[b]Quinolizinium as Fluorosolvatochromic Probe. J Fluoresc 27, 1221–1224 (2017). https://doi.org/10.1007/s10895-017-2107-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-017-2107-1