Pillar[5]arene and Azine Derivative Assembly Improved Dual-Channel Detection of CN–
Qing-Ling Su
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorJin-Fa Chen
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorXiao-Mei Sun
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorJuan Liu
Key Laboratory of Environment-Friendly Composite Materials of the State Ethnic Affairs Commission, Gansu Provincial Biomass Function Composites Engineering Research Center, College of Chemical Engineering, Northwest Minzu University (Northwest University for Nationalities), Xibei Xincun, Lanzhou, Gansu, 730000 China
Search for more papers by this authorXin-Yu Dai
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorTai-Bao Wei
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorHong Yao
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorCorresponding Author
Qi Lin
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
E-mail: [email protected]Search for more papers by this authorQing-Ling Su
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorJin-Fa Chen
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorXiao-Mei Sun
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorJuan Liu
Key Laboratory of Environment-Friendly Composite Materials of the State Ethnic Affairs Commission, Gansu Provincial Biomass Function Composites Engineering Research Center, College of Chemical Engineering, Northwest Minzu University (Northwest University for Nationalities), Xibei Xincun, Lanzhou, Gansu, 730000 China
Search for more papers by this authorXin-Yu Dai
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorTai-Bao Wei
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorHong Yao
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
Search for more papers by this authorCorresponding Author
Qi Lin
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
The cyanide anion (CN–) is known to be one of the most toxic anions. Therefore, there is an urgent need to develop a reliable, sensitive, selective, rapid and effective method for the detection of CN–. Here, a self-assembly strategy based on pillar[5]arene P5 and azine derivative AZ was used to construct supramolecular sensors, and it was found that the detection effect of CN– was significantly improved by the assembly strategy. The sensitivity of the assembled sensor P5-AZ to CN– is more than 10 times higher than that of AZ. The detect mechanism was further investigated by theoretical calculations and 1H NMR. The results showed that AZ detects CN– by a deprotonation process with fluorescence enhancement, while P5-AZ improves the sensitivity of CN– recognition through hydrogen bonding, anion-π and anion-dipole interactions, as well as the strong bonding ability of the assembly. Supramolecular assembly P5-AZ has the advantages of low toxicity, high sensitivity, and more importantly, it provides a method to detect CN– sensitivity in the aqueous phase and organisms by host-guest assembly.
Supporting Information
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Appendix S1: Supporting Information |
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References
- 1 Wang, F.; Wang, L.; Chen, X.; Yoon, J. Recent Progress in the Development of Fluorometric and Colorimetric Chemosensors for Detection of Cyanide Ions. Chem. Soc. Rev. 2014, 43, 4312–4324.
- 2 Liu, S.; Yang, M.; Liu, Y.; Chen, H.; Li, H. A Novel “Turn-on” Fluorescent Probe Based on Triphenylimidazole-Hemicyanine Dyad for Colorimetric Detection of CN– in 100% Aqueous Solution. J. Hazard. Mater. 2018, 344, 875–882.
- 3 Bai, C. B.; Zhang, J.; Qiao, R.; Zhang, Q. Y.; Mei, M. Y.; Chen, M. Y.; Qu, C. Q. Reversible and Selective Turn-on Fluorescent and Naked-Eye Colorimetric Sensor to Detect Cyanide in Tap Water, Food Samples, and Living Systems. Ind. Eng. Chem. Res. 2020, 59, 8125–8135.
- 4 Yilmaz, B.; Keskinates, M.; Aydin, Z.; Bayrakci, M. A Highly Selective Optical Sensor for the Detection of Cyanide Ions in Aqueous Solution and Living Cells. J. Photochem. Photobiol. A 2022, 424, 113651.
- 5 WHO Guidelines for Drinking-Water Quality, World Health Organization, Geneva, Switzerland, 2011, p. 342.
- 6 Guidelines for Drinking-water Quality, World Health Organization, Geneva, 1996.
- 7 Du, J.; Hu, M.; Fan, J.; Peng, X. Fluorescent Chemodosimeters Using “Mild” Chemical Events for the Detection of Small Anions and Cations in Biological and Environmental Media. Chem. Soc. Rev. 2012, 41, 4511–4535.
- 8 Wu, W.; Xiao, Q.; Zhang, P.; Ye, M.; Wan, Y.; Liang, H. Rapid Measurement of Free Cyanide in Liquor by Ion Chromatography with Pulsed Amperometric Detection. Food Chem. 2015, 172, 681–684.
- 9 Zhang, C. S.; Zheng, H.; Ouyang, J.; Feng, S. Z.; Taes, Y. E. C. Cyanide Distribution in Human Tissue, Determined by GC/ECD/HS. Anal. Lett. 2005, 38, 247–256.
- 10 Mahmoud, A. M.; Mahnashi, M. H.; El-Wekil, M. M. Indirect Differential Pulse Voltammetric Analysis of Cyanide at Porous Copper Based Metal Organic Framework Modified Carbon Paste Electrode: Application to Different Water Samples. Talanta 2021, 221, 121562.
- 11 Bakht, B. K.; Zali-Boeini, H.; Torabi, M.; Shams-Harandi, M., Shams, E.; Farahbakhsh, Z.; Varma, R. S. Optical, Electrochemical, and Test Strip Methods for Sensitive and Selective Detection of Cyanide Ion Using a Multifunctional π-Extended Azaacene-Based System. Sens. Actuators B Chem. 2023, 379, 133280.
- 12 Chen, J.; Li, W.; Li, Q.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. A Turn-On Fluorescence Chemosensor for Cyanide in Aqueous Media Based on a Nucleophilic Addition Reaction. Chin. J. Chem. 2017, 35, 1165–1169.
- 13 Zhang, P.; Shi, B.; You, X.; Zhang, Y.; Lin, Q.; Yao, H.; Wei, T. A Highly Selective and Sensitive Chemosensor for Instant Detection Cyanide via Different Channels in Aqueous Solution. Tetrahedron 2014, 70, 1889–1894.
- 14 Hou, L.; Li, F.; Guo, J.; Zhang, X.; Kong, X.; Cui, X. T.; Shuang, S. A Colorimetric and Ratiometric Fluorescent Probe for Cyanide Sensing in Aqueous Media and Live Cells. J. Mater. Chem. B 2019, 7, 4620–4629.
- 15 Dong, Z. M.; Ren, H.; Wang, J. N.; Chao, J. B.; Wang, Y. A New Colorimetric and Ratiometric Fluorescent Probe for Selective Recognition of Cyanide in Aqueous Media. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2019, 217, 27–34.
- 16 Junaid, H. M.; Waseem, M. T.; Khan, Z. A.; Munir, F.; Sohail, S.; Farooq, U.; Shahzad, S. A. Fluorenone-Based Fluorescent and Colorimetric Sensors for Selective Detection of I- Ions: Applications in HeLa Cell Imaging and Logic Gate. ACS Omega 2022, 7, 9730–9742.
- 17 Dias, G. G.; Rodrigues, M. O.; Paz, E. R. S.; Nunes, M. P.; Araujo, M. H.; Rodembusch, F. S.; da Silva Júnior, E. N. Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors. ACS Sensors 2022, 7, 2865–2919.
- 18 Zhong, X.; Li, Z.; Shi, R.; Yan, L.; Zhu, Y.; Li, H. Schiff Base-Modified Nanomaterials for Ion Detection: A Review. ACS Appl. Nano Mater. 2022, 5, 13998–14020.
- 19 Tharmalingam, B.; Mathivanan, M.; Dhamodiran, G.; Mani, K. S.; Paranjothy, M.; Murugesapandian, B. Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On-Off-On Emissive Response to Cu2+/S2-. ACS Omega 2019, 4, 12459–12469.
- 20 Li, Y.; Dahal, D.; Abeywickrama, C. S.; Pang, Y. Progress in Tuning Emission of the Excited-State Intramolecular Proton Transfer (ESIPT)-Based Fluorescent Probes. ACS Omega 2021, 6, 6547–6553.
- 21 Wu, F.; Wang, L.; Tang, H.; Cao, D. Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents. Anal. Chem. 2019, 91, 5261–5269.
- 22 Das, R.; Bej, S.; Hirani, H.; Banerjee, P. Trace-Level Humidity Sensing from Commercial Organic Solvents and Food Products by an AIE/ESIPT-Triggered Piezochromic Luminogen and ppb-Level “OFF-ON-OFF” Sensing of Cu2+: A Combined Experimental and Theoretical Outcome. ACS Omega 2021, 6, 14104–14121.
- 23 McLaughlin, B.; Surender, E. M.; Wright, G. D.; Daly, B.; de Silva, A. P. Lighting-up Protein-Ligand Interactions with Fluorescent PET (Photoinduced Electron Transfer) Sensor Designs. Chem. Commun. 2018, 54, 1319–1322.
- 24 Karmakar, M.; Bhatta, S. R.; Giri, S.; Thakur, A. Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin-Quinoline Platform: Application in Cascaded Molecular Logic. Inorg. Chem. 2020, 59, 4493–4507.
- 25 Daly, B.; Ling, J.; de Silva, A. P. Current Developments in Fluorescent PET (Photoinduced Electron Yransfer) Sensors and Switches. Chem. Soc. Rev. 2015, 44, 4203–4211.
- 26 Mondal, A.; Hazra, A.; Chakrabarty, J.; Bose, K. J. C.; Banerjee, P. Tandem Detection of Sub-Nano Molar Level CN– and Hg2+ in Aqueous Medium by a Suitable Molecular Sensor: A Viable Solution for Detection of CN– and Development of the RGB-Based Sensory Device. ACS Omega 2020, 5, 6576–6587.
- 27 Yu, Z.; Ma, W.; Wu, T.; Wen, J.; Zhang, Y.; Wang, L.; Hu, M. Coumarin-Modified Graphene Quantum Dots as a Sensing Platform for Multicomponent Detection and Its Applications in Fruits and Living Cells. ACS Omega 2020, 5, 7369–7378.
- 28 Stock, R. I.; Dreyer, J. P.; Nunes, G. E.; Bechtold, I. H.; Machado, V. G. Optical Chemosensors and Chemodosimeters for Anion Detection Based on Merrifield Resin Functionalized with Brooker's Merocyanine Derivatives. ACS Appl. Polym. Mater. 2019, 1, 1757–1768.
- 29 Paul, S.; Das, R.; Seth, M.; Hirani, H.; Murmu, N. C.; Banerjee, P. A Urea-Functionalized Chemoreceptor for Expeditious Chromogenic Recognition of Toxic Industrial Pollutants Cu2+ and CN– from Real Water Sources and Biofluids: Diagnosis of Wilson's disease from Human Urine. Ind. Eng. Chem. Res. 2020, 59, 19077–19092.
- 30 Bai, C. B.; Zhang, J.; Qiao, R.; Zhang, Q. Y.; Mei, M. Y.; Chen, M. Y.; Qu, C. Q. Reversible and Selective Turn-on Fluorescent and Naked-Eye Colorimetric Sensor to Detect Cyanide in Tap Water, Food Samples, and Living Systems. Ind. Eng. Chem. Res. 2020, 59, 8125–8135.
- 31 Zhang, C.; Wang, Y.; Zhang, L.; Li, X.; Nie, S.; Liu, C. A Near-Infrared Fluorescent Probe Based on Phenothiazine for Rapid Detecting of CN– and ClO–. Opt. Mater. 2022, 133, 112959.
- 32 Pei, P. X.; Hu, J. H.; Long, C.; Ni, P. W. A Novel Colorimetric and “Turn-on” Fluorimetric Chemosensor for Selective Recognition of CN– Ions Based on Asymmetric Azine Derivatives in Aqueous Media. Spectrochim. Acta A Mol. Biomol. 2018, 198, 182–187.
- 33 Khanra, S.; Ta, S.; Ghosh, M.; Chatterjee, S.; Mukherjee, P.; Das, D. Al3+ Triggered Aggregation Induced Emission of an Anthracence Based Azine Derivative in SDS Medium. New J. Chem. 2020, 44, 8477–8485.
- 34 Bhosle, A. A.; Hiremath, S. D.; Bhasikuttan, A. C.; Banerjee, M.; Chatterjee, A. Solvent-Free Mechanochemical Aynthesis of a Novel Benzothiazole-azine Based ESIPT-Coupled Orange AIEgen for the Selective Recognition of Cu2+ Ions in Solution and Solid Phase. J. Photochem. 2021, 413, 113265–113276.
- 35 Sawminathan, S.; Munusamy, S.; Manickam, S.; Jothi, D.; KulathuIyer, S. Azine Based Fluorescent Rapid "Off-On" Chemosensor for Detecting Th4+ and Fe3+ Ions and Its Real-Time Application. Dyes Pigm. 2021, 196, 109755.
- 36 Rehberg, N.; Sommer, G. A.; Drießen, D.; Kruppa, M.; Adeniyi, E. T.; Chen, S.; Kalscheuer, R. Nature-Inspired (di)Azine-Bridged Bisindole Alkaloids with Potent Antibacterial in vitro and in vivo Efficacy against Methicillin-Resistant Staphylococcus aureus. J. Med. Chem. 2020, 63, 12623–12641.
- 37 Bagheri, M.; Masoomi, M. Y. Sensitive Ratiometric Fluorescent Metal-Organic Framework Sensor for Calcium Signaling in Human Blood Ionic Concentration Media. ACS Appl. Mater. Interfaces 2020, 12, 4625–4631.
- 38 Jiang, Q.; Sun, N.; Li, Q.; Si, W.; Li, J.; Li, A.; Wang, J. Redox-Responsive Pickering Emulsions Based on Silica Nanoparticles and Electrochemical Active Fluorescent Molecules. Langmuir 2019, 35, 5848–5854.
- 39 Shen, Y.; Li, M.; Yang, M.; Zhang, Y.; Li, H.; Zhang, X. A Specific AIE and ESIPT Fluorescent Probe for Peroxynitrite Detection and Imaging in Living Cells. Spectrochim. Acta A Mol. Biomol. 2019, 222, 117230.
- 40 Zhou, F.; Zhang, K.; Li, G.; Gui, C.; Hu, R.; Li, S.; Tang, B. Z. Keto-Salicylaldehyde Azine: a Kind of Novel Building Block for AIEgens and Its Application in Tracking Lipid Droplets. Mater. Chem. Front. 2020, 4, 3094–3102.
- 41 Deng, Q.; Ding, K.; Li, Y.; Jiao, Y.; Hu, R.; Zhang, T.; Tang, B. Z. Referential Modification Strategy Based on Phenolic Hydroxyl-containing KSA Luminogens for ER-targeting Probe Construction. Biomaterials 2022, 289, 121767.
- 42 Cai, Y.; Yan, X.; Wang, S.; Zhu, Z.; Cen, M.; Ou, C.; Yao, Y. Pillar[5]arene-Based 3D Hybrid Supramolecular Polymer for Green Catalysis in Water. Inorg. Chem. 2021, 60, 2883–2887.
- 43 Cui, W.; Tang, H.; Xu, L.; Wang, L.; Meier, H.; Cao, D. Pillar[5]arene-Diketopyrrolopyrrole Fluorescent Copolymer: A Promising Recognition and Adsorption Material for Adiponitrile by Selective Formation of a Conjugated Polypseudorotaxane. Macromol. Rapid Commun. 2017, 38, 1700161.
- 44 Yin, C.; Yan, Z. A.; Ma, X. A Supramolecular Assembly Strategy towards Organic Luminescent Materials. Chem. Commun. 2023, 59, 13421–13433.
- 45 Wang, Y.; Ping, G.; Li, C. Efficient Complexation Between Pillar[5]arenes and Neutral Guests: from Host-Guest Chemistry to Functional Materials. Chem. Commun. 2016, 52, 9858–9872.
- 46 Zhang, H.; Liu, Z.; Zhao, Y. Pillararene-based Self-assembled Amphiphiles. Chem. Soc. Rev. 2018, 47, 5491.
- 47 Yao, Y.; Xue, M.; Zhang, Z.; Zhang, M.; Wang, Y.; Huang, F. Gold Nanoparticles Stabilized by an Amphiphilic Pillar[5]arene: Preparation, Self-assembly into Composite Microtubes in Water and Application in Green Catalysis. Chem. Sci. 2013, 4, 3667–3672.
- 48 Acikbas, Y.; Aksoy, M.; Aksoy, M.; Karaagac, D.; Bastug, E.; Erdoğan, M.; Ersoz, M. Recent progress in pillar[n]arene-based Thin Films on Chemical Sensor Applications. J. Incl. Phenom. Macrocycl. Chem. 2021, 100, 1–16.
- 49 Bastug, E.; Oguz, A.; Oguz, M.; Yilmaz, M. A Highly Branched Macrocycle-Based Dual-Channel Sensor: Bodipy and Pillar[5]arene Combination for Detection of Sn (II) &Hg (II) and Bioimaging in Living Cells. Anal. Chim. Acta 2022, 1196, 339542.
- 50 Bilgiç, A.; Çimen, A. A Novel Biosorbent Functionalized Pillar[5]arene: Synthesis, Characterization and Effective Biosorption of Cr(VI). Sci. Total Environ. 2022, 857, 159312.
- 51 Liman, R.; Ciğerci, İ.; Ozmen, M.; Acikbas, Y. Assessment of the Cytotoxic and Genotoxic Potential of Pillar[5]arene Derivatives by Allium Cepa Roots and Drosophila Melanogaster Haemocytes. Ecotoxicol. Environ. Saf. 2020, 192, 110328.
- 52 Li, J.; Chang, Z.; Pan, X.; Dong, W.; Jia, A. Q. A Novel Colorimetric and Fluorescent Probe Based on Indolium Salt for Detection of Cyanide in 100% Aqueous Solution. Dyes Pigm. 2019, 168, 175–179.
- 53 Long, L.; Han, Y.; Yuan, X.; Cao, S.; Liu, W.; Chen, Q.; Han, Z. A Novel Ratiometric Near-Infrared Fluorescent Probe for Monitoring Cyanide in Food Samples. Food Chem. 2020, 331, 127359.
- 54 Vanita, V.; Walia, A.; Chae, P.; Kumar, S. Pyridoanthrone-Based Chromo-Fluorogenic Amphiphiles for Selective CN− Detection and Their Bioimaging Application. Sens. Actuators B Chem. 2019, 304, 127396.
- 55 Kang, J. H.; Lee, S. Y.; Ahn, H. M.; Kim, C. A Novel Colorimetric Chemosensor for the Sequential Detection of Ni2+ and CN− in Aqueous Solution. Sens. Actuators B Chem. 2017, 242, 25–34.
- 56 Jiang, P.; Wu, S.; Liu, J.; Fu, S.; Hu, Q.; Yan, X.; Yang, Q. Novel Acylhydrazone-Based Supramolecular Gel for Super-Sensitive Detection of Fe3+ and Alternant Detection of CN− in Aqueous Medium. Opt. Mater. 2022, 129, 112468.
- 57 Zhang, X.; Chen, S.; Jin, S.; Lu, X.; Li, L.; Chen, X.; Shu, Q. Naphthalene Based Lab-on-A-Molecule for the Highly Selective and Sensitive Detection of CN− and Ag+ in Aqueous Solution. Sens. Actuators B Chem. 2016, 237, 367–372.
- 58 Jeyasingh, V.; Murugesan, K.; Lakshminarayanan, S.; Selvapalam, N.; Das, G.; Piramuthu, L. A Molecular Phototropic System for Cyanide: Detection and Sunlight Driven Harvesting of Cyanide with Molecular Sunflower. Spectochim. Acta A 2020, 234, 118207.
- 59 Kaushik, R.; Ghosh, A.; Singh, A.; Gupta, P.; Mittal, A.; Jose, D. A. Selective Detection of Cyanide in Water and Biological Samples by an Off-the-Shelf Compound. ACS Sensors. 2016, 1, 1265–1271.
- 60 Huang, T. T.; Wang, Z. H.; Li, Y. J.; Yang, Q. Y.; Wei, T. B.; Yao, H.; Lin, Q. Novel Tetra-Arm Chemosensor Supply “Collaboration Effect” for Highly Sensitive Fluorescent and Colorimetric Sensing of L-Arg. Dyes Pigm. 2021, 194, 109658.
- 61 Devendhiran, T.; Kumarasamy, K.; Lin, M. C.; Yang, Y. X. Synthesis and Physical Studies of Coumarin-Based Chemosensor for Cyanide Ions. Inorg. Chem. Commun. 2021, 134, 108951.