Abstract
A new chalcone-based probe containing coumarin and naphthol at both ends has been synthesized via aldol condensation. The uniqueness of the newly derived probe can be ascribed to the presence of naphthol and coumarin units acting as binding site and signaling element, respectively. The fluorogenic behaviors toward various anions were investigated. The probe was characterized by various spectroscopic techniques and the in-depth study led to show excellent selectivity and sensitivity for fluoride ions. The hydrogen bonding thus formed with fluoride anion provides remarkable fluorometric responses. The interactions of the probe with fluoride ions were determined by fluorescence, FT-IR and NMR spectroscopic techniques. The exploratory studies by fluorescent spectral changes augur well for the naked-eye sensing applications.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Udhayakumari D, Velmathi S, Chen W-C, S-P W (2014) A dual-mode chemosensor: highly selective colorimetric fluorescent probe for Cu2+ and F− ions. Sensors Actuators B Chem 204:375–381
Velmathi S, Reena V, Suganya S, Anandan S (2012) Pyrrole based Schiff bases as colorimetric and fluorescent chemosensors for fluoride and hydroxide anions. J Fluoresc 22:155–162
Bai B, Mao X, Wei J, Wei Z, Wang H, Li M (2015) Selective anion-responsive organogel based on a gelator containing hydrazide and azobenzene units. Sensors Actuators B Chem 211:268–274
Kaur N, Kumar S (2011) Colorimetric metal ion sensors. Tetrahedron 67:9233–9264
Zhu M, Yuan M, Liu X, Xu J, Lv J, Huang C, Liu H, Li Y, Wang S, Zhu D (2008) Visible near-infrared chemosensor for mercury ion. Org Lett 10:1481–1484
Cheng C-C, Chen Z-S, C-Y W, Lin C-C, Yang C-R, Yen Y-P (2009) Azo dyes featuring a pyrene unit: new selective chromogenic and fluorogenic chemodosimeters for Hg(II. Sensors Actuators B Chem 142:280–287
Bao Y, Liu B, Wang H, Tian J, Bai R (2011) A “naked eye” and ratiometric fluorescent chemosensor for rapid detection of F− based on combination of desilylation reaction and excited-state proton transfer. Chem Commun 47:3957
Hrishikesan E, Kannan P (2013) Azobenzene chemosensor based on nitrogen chelator for the detection of Cu (II) ion in aqueous medium. Inorg Chem Commun 37:21–25
Zhang Y-M, Lin Q, Wei T-B, Wang D-D, Yao H, Wang Y-L (2009) Simple colorimetric sensors with high selectivity for acetate and chloride in aqueous solution. Sensors Actuators B Chem 137:447–455
Jose DA, Kumar DK, Ganguly B, Das A (2004) Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites. Org Lett 6:3445–3448
Shao J, Yu M, Lin H, Lin H (2008) A novel fluorescent and colorimetric anion sensor based on thiourea derivative in competitive media. Spectrochim Acta A Mol Biomol Spectrosc 70:1217–1221
Duke RM, Veale EB, Pfeffer FM, Kruger PE, Gunnlaugsson T (2010) Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. Chem Soc Rev 39:3936–3953
Piatek P, Jurczak J (2002) A selective colorimetric anion sensor based on an amide group containing macrocycle. Chem Commun:2450–2451
Wu J, Liu W, Ge J, Zhang H, Wang P (2011) New sensing mechanisms for design of fluorescent chemosensors emerging in recent years. Chem Soc Rev 40:3483–3495
Peng X, Wu Y, Fan J, Tian M, Han K (2005) Colorimetric and ratiometric fluorescence sensing of fluoride: tuning selectivity in proton transfer. J Org Chem 70:10524–10531
Xu S, Chen K, Tian H (2005) A colorimetric and fluorescent chemodosimeter: fluoride ion sensing by an axial-substituted subphthalocyanine. J Mater Chem 15:2676–2680
Bhosale SV, Bhosale SV, Kalyankar MB, Langford SJ (2009) A core-substituted naphthalene diimide fluoride sensor. Org Lett 11:5418–5421
Gong H-L, Jiang Y, Hou R-C, Ding X-Q (2016) A sensitive and selective fluorescent coumarin-based probe for detection of hypochlorite ion and its application to cellular imaging. J Fluoresc 26:403–406
Xiao Y-H, Xi G, Zhao X-X, Zhou S, Zhou Z-Q, Zhao B-X (2015) A novel coumarin-based fluorescent probe for the detection of hydrazine both in aqueous solution and vapor state. J Fluoresc 25:1023–1029
Zhou Y, Zhang J-F, Yoon J (2014) Fluorescence and colorimetric chemosensors for fluoride-ion detection. Chem Rev 114:5511–5571
Vijayaraghavan R, Sivalingam S, Sivan V (2013) Synthesis and anion binding studies of azo-Schiff bases: selective colorimetric fluoride and acetate ion sensors. J Fluor Chem 153:89–95
Li Y, Li J, Lin H, Shao J, Cai Z-S, Lin H (2010) A Novel Colorimetric Receptor Responding AcO- Anions Based on an Azo Derivative in DMSO and DMSO/Water Solution. J Lumin 130:466–472
Shao J, Lin H, Lin H (2009) A novel chromo-and fluorogenic dual responding H 2 PO 4− receptor based on an azo derivative, Dyes Pigments 80, 259–263.
Acknowledgments
The main author (G.-Y. Yeap) gratefully acknowledges Malaysian Ministry of Higher Education (MOHE) for funding this project through FRGS Grant No.203/PKIMIA/6711422.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yeap, GY., Hrishikesan, E., Chan, YH. et al. A New Emissive Chalcone-Based Chemosensor Armed by Coumarin and Naphthol with Fluorescence “Turn-on” Properties for Selective Detection of F− Ions. J Fluoresc 27, 105–110 (2017). https://doi.org/10.1007/s10895-016-1938-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-016-1938-5