Synthesis, Characterization, Fluoride Ion Sensing and DFT Studies of Carbamate-Based Bistriazole

References

• J.-M. Lehn, “Molecular and Supramolecular Devices,” in Supramolecular Chemistry (Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 1995).
   Google Scholar
• W. Gopel, J. Hesse, and J. N. Zemel, “Sensors: A Comprehensive Survey” (Hoboken, NJ, USA: Wiley, 1989.
   Google Scholar
• N. Zaccheroni, F. Palomba, and E. Rampazzo, “Luminescent Chemosensors: From Molecules to Nanostructures,” in Applied Photochemistry: When Light Meets Molecules, edited by G. Bergamini and S. Silvi (Cham, Switzerland: Springer International Publishing, 2016).
   Google Scholar
• Y. Kubo, M. Yamamoto, M. Ikeda, M. Takeuchi, S. Shinkai, S. Yamaguchi, and K. Tamao, “A Colorimetric and Ratiometric Fluorescent Chemosensor with Three Emission Changes: Fluoride Ion Sensing by a Triarylborane–Porphyrin Conjugate,” Angewandte Chemie (International ed. in English) 42, no. 18 (2003): 2036–40.
   PubMed Web of Science ®Google Scholar
• D. Udhayakumari, S. Naha, and S. Velmathi, “Colorimetric and Fluorescent Chemosensors for Cu 2+. A Comprehensive Review from the Years 2013–15,” Analytical Methods 9, no. 4 (2017): 552–78.
   Web of Science ®Google Scholar
• Y. Zhou, J. F. Zhang, and J. Yoon, “Fluorescence and Colorimetric Chemosensors for Fluoride-Ion Detection,” Chemical Reviews 114, no. 10 (2014): 5511–71.
   PubMed Web of Science ®Google Scholar
• Z. Yu-Hui and B. Xiaoping, “Synthesis, Recognition and Sensing Properties of Dipyrrolylmethane-Based Anion Receptors,” Spectrochimica Acta A 210 (2019): 1–8.
   Web of Science ®Google Scholar
• R. Martinez-Manez and F. Sancenon, “Fluorogenic and Chromogenic Chemosensors and Reagents for Anions,” Chemical Reviews 103 (2003): 4419–76.
   PubMed Web of Science ®Google Scholar
• David Esteban-Gómez, Luigi Fabbrizzi, and Maurizio Licchelli, “Why, on interaction of urea-based receptors with fluoride, beautiful colors develop,” The Journal of Organic Chemistry 70, no. 14 (2005): 5717–20.
   PubMed Web of Science ®Google Scholar
• T. S. Pandian and J. Kang, “Participation of Aliphatic C–H Hydrogen Bonding in Anion Recognition,” Tetrahedron Letters. 56, no. 28 (2015): 4191–4.
   Web of Science ®Google Scholar
• N. Ieda, H. Nakagawa, T. Peng, D. Yang, T. Suzuki, and N. Miyata, “Photocontrollable Peroxynitrite Generator Based on N-Methyl-N-Nitrosoaminophenol for Cellular Application,” Journal of the American Chemical Society 134, no. 5 (2012): 2563–8.
   PubMed Web of Science ®Google Scholar
• J. Du, M. Hu, J. Fan, and X. Peng, “Fluorescent Chemodosimeters Using "Mild" Chemical Events for the Detection of Small Anions and Cations in Biological and Environmental Media”, Chemical Society Reviews 41, no. 12 (2012): 4511–35.
   PubMed Web of Science ®Google Scholar
• I. Hussain, K. U. Ahamad, and P. Nath, “Low-Cost, Robust, and Field Portable Smartphone Platform Photometric Sensor for Fluoride Level Detection in Drinking Water,” Analytical Chemistry 89, no. 1 (2017): 767–75.
   PubMed Web of Science ®Google Scholar
• S. Ayoob and A. K. Gupta, “Fluoride in Drinking Water: A Review on the Status and Stress Effects,” Critical Reviews in Environmental Science and Technology 36, no. 6 (2006): 433–87.
   Web of Science ®Google Scholar
• C. M. Carey, “Focus on Fluorides: Update on the Use of Fluoride for the Prevention of Dental Caries,” Journal of Evidence Based Dental Practice 14 (2014): 95–102.
   PubMed Web of Science ®Google Scholar
• E. T. Everett, “Fluoride's Effects on the Formation of Teeth and Bones, and the Influence of Genetics,” Journal of Dental Research 90, no. 5 (2011): 552–60.
   PubMed Web of Science ®Google Scholar
• E. H. Van Veen, M. T. C. De Loos-Vollebregt, A. P. Wassink, and H. Kalter, “Determination of Trace Elements in Uranium by Inductively Coupled Plasma-Atomic Emission Spectrometry Using Kalman Filtering,” Analytical Chemistry 64, no. 15 (1992): 1643–9.
   Web of Science ®Google Scholar
• A. A. Orlov, A. F. Tsimbalyuk, and R. V. Malyugin, “Desublimation for Purification and Transporting UF6: Process Description and Modeling,” Separation and Purification Reviews 46, no. 1 (2017): 81–9.
   Web of Science ®Google Scholar
• K. L. Kirk, “Biochemistry of Inorganic Bromide,” in Biochemistry of the Elemental Halogens and Inorganic Halides. vol 9A + B (Boston, MA: Springer, 1991).
   Google Scholar
• Weatherall J. A, in Pharmacology of Fluorides in Handbook of Experimental Pharmacology, Part 1 XX/1 (Berlin: Springer, 1969), 141–72.
   Google Scholar
• M. Kleerekoper, “The Role of Fluoride in the Prevention of Osteoporosis,” Endocrinology and Metabolism Clinics of North America 27, no. 2 (1998): 441–52.
   PubMed Web of Science ®Google Scholar
• L. Valdez Jiménez, O. D. López Guzmán, M. Cervantes Flores, R. Costilla-Salazar, J. Calderón Hernández, Y. Alcaraz Contreras, and D. O. Rocha-Amador, “In Utero Exposure to Fluoride and Cognitive Development Delay in Infants,” Neurotoxicology 59 (2017): 65–70.
   PubMed Web of Science ®Google Scholar
• J. Tummachote, W. Punyain, S. Thanomsak, A. Sirikulkajorn, and B. Tomapatanaget, “Colorimetric N-Butyl-3,6-Diamidecarbazole-Based Chemosensors for Detection of Fluoride and Cyanide Anions,” Spectrochimica Acta: Part A, Molecular and Biomolecular Spectroscopy 214 (2019): 384–92.
   PubMed Web of Science ®Google Scholar
• F. Qi, F. Zhang, L. Mo, X. Ren, Y. Wang, X. Li, X. Liu, Y. Zhang, Z. Yang, and X. Song, “A HBT-Based Bifunctional Fluorescent Probe for the Ratiometric Detection of Fluoride and Sulphite in Real Samples,” Spectrochimica Acta: Part A, Molecular and Biomolecular Spectroscopy 219 (2019): 547–51.
   PubMed Web of Science ®Google Scholar
• P. A. Gale, “Anion Receptor Chemistry: Highlights from 1999,” Coordination Chemistry Reviews 213, no. 1 (2001): 79–128.
   Google Scholar
• P. A. Gale, “Anion and Ion-Pair Receptor Chemistry: highlights from 2000 and 2001,” Coordination Chemistry Reviews. 240, no. 1–2 (2003): 191–221.
   Web of Science ®Google Scholar
• J. L. Sessler and J. M. Davis, “Sapphyrins: Versatile Anion Binding Agents,” Accounts of Chemical Research 34, no. 12 (2001): 989–97.
   PubMed Web of Science ®Google Scholar
• H. M. Chawla, S. N. Sahu, and R. Shrivastava, “A Novel Calix[4]Arene-Based Neutral Semicarbazone Receptor for Anion Recognition,” Tetrahedron Letters 48, no. 34 (2007): 6054–8.
   Web of Science ®Google Scholar
• K. Choi and A. D. Hamilton, “Macrocyclic Anion Receptors Based on Directed Hydrogen Bonding Interactions,” Coordination Chemistry Reviews 240, no. 1–2 (2003): 101–10.
   Web of Science ®Google Scholar
• E. B. Veale, G. M. Tocci, F. M. Pfeffer, P. E. Kruger, and T. Gunnlaugsson, “Demonstration of Bidirectional Photoinduced Electron Transfer (PET) Sensing in 4-Amino-1,8-Naphthalimide Based Thiourea Anion Sensors,” Organic and Biomolecular Chemistry 7, no. 17 (2009): 3447–54.
   PubMed Web of Science ®Google Scholar
• C. R. Bondy and S. J. Loeb, “Amide Based Receptors for Anions,” Coordination Chemistry Reviews 240, no. 1–2 (2003): 77–9.
   Web of Science ®Google Scholar
• D. Makuc, M. Lenarcic, G. W. Bates, P. A. Gale, and J. Plavec, “Anion-Induced Conformational Changes in 2,7-Disubstituted Indole-Based Receptors,” Organic and Biomolecular Chemistry 7, no. 17 (2009): 3505–11.
   PubMed Web of Science ®Google Scholar
• P. R. Edwards, J. R. Hiscock, P. A. Gale, and M. E. Light, “Carbamate Complexation by Urea-Based Receptors: Studies in Solution and the Solid State,” Organic and Biomolecular Chemistry 8, no. 1 (2010): 100–6.
   PubMed Web of Science ®Google Scholar
• P. Anzenbacher, R. Nishiyabu, and M. A. Palacios, “N-Confused Calix[4]Pyrroles,” Coordination Chemistry Reviews 250, no. 23–24 (2006): 2929–38.”
   Web of Science ®Google Scholar
• Z. Xu, S. K. Kim, and J. Yoon, “Revisit to Imidazolium Receptors for the Recognition of Anions: Highlighted Research During 2006–2009,” Chemical Society Reviews 39, no. 5 (2010): 1457–66.
   PubMed Web of Science ®Google Scholar
• J. J. He and F. A. Quiocho, “A Nonconservative Serine to Cysteine Mutation in the Sulfate-Binding Protein, A Transport Receptor,” Science (New York, NY) 251, no. 5000 (1991): 1479–81.
   Google Scholar
• E. B. Veale, D. O. Frimannsson, M. Lawler, and T. Gunnlaugsson, “4-Amino-1,8-Naphthalimide-Based Tröger's Bases as High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds,” Organic Letters 11, no. 18 (2009): 4040–3.
   PubMed Web of Science ®Google Scholar
• V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, “A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes,” Angewandte Chemie International Edition 41, no. 14 (2002): 2596–9.
   PubMed Web of Science ®Google Scholar
• H. C. Kolb, M. G. Finn, and K. B. Sharpless, “Click Chemistry: Diverse Chemical Function from a Few Good Reactions,” Angewandte Chemie International Edition 40, no. 11 (2001): 2004–21.
   PubMed Web of Science ®Google Scholar
• J. Li, G. Ding, Y. Niu, L. Wu, H. Feng, and W. He, “The Structural Properties of 5-Methyl-2-Phenyl-2H-1,2,3-Triazole-4-Carboxylic Acid and Chromogenic Mechanism on its Rhodamine B Derivatives to Hg2+ Ions,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 200 (2018): 127–35.
   PubMed Web of Science ®Google Scholar
• P. Rani, K. Lal, V. D. Ghule, and R. Shrivastava, “Green Synthesis of Triazole-Based Chemosensors and Their Efficacy towards Mercury Sensing,” Current Analytical Chemistry 16, no. 6 (2020): 738–6.
   Web of Science ®Google Scholar
• X. Liang, Y. Li, Y. Yu, T. Liu, C. Songhua, L. Huibiao, and Y. Li, “A Receptor Incorporating OH, NH and CH Binding Motifs for a Fluoride Selective Chemosensor,” Organic and Biomolecular Chemistry 10, no. 22 (2012): 4375–80.
   PubMed Web of Science ®Google Scholar
• V. Haridas, S. Srikanta, and P. P. Praveen Kumar, “Triazole-Based Chromogenic and Non-Chromogenic Receptors for Halides,” Tetrahedron Letters 52, no. 51 (2011): 6930–4.
   Web of Science ®Google Scholar
• K. Aiken, B. Jessica, S. Steven, C. Matthew, W. Domonique, F. Christian, P. Clifford, C. McMillen, D. Ghosh, and S. Landge, “Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing,” Magnetochemistry 4, no. 1 (2018): 15–32.
   Web of Science ®Google Scholar
• João Guilherme P. Mendonça, Josué M. Silla, Laize A. F. Andrade, Sergio A. Fernandes, Rodrigo A. Cormanich, and Matheus P. Freitas, “Theoretical and NMR Experimental Insights on Urea, Thiourea and Diindolyurea as Fluoride Carriers,” Journal of Molecular Structure 1114 (2016): 13–20.
   Web of Science ®Google Scholar
• M. Boiocchi, L. Del Boca, D. E. Go ’Mez, L. Fabbrizzi, M. Licchelli, and E. Monzani, “Nature of Urea–Fluoride Interaction: Incipient and Definitive Proton Transfer,” Journal of the American Chemical Society 126, no. 50 (2004): 16507–14.
   PubMed Web of Science ®Google Scholar
• B. H. M. Snellink-Rue, M. M. G. Antonisse, J. F. J. Engbersen, P. Timmerman, and D. N. Reinhoudt, “Neutral Anion Receptors with Multiple Urea‐Binding Sites,” European Journal of Organic Chemistry 2000, no. 1 (2000): 165–70.
   Web of Science ®Google Scholar
• O. Ozay, M. Yildirim, and H. Ozay, “Synthesis, Structural Characterization, and Anion Interactions of New Triazole-Linked Urea Derivative Fully Substituted Cyclotriphosphazene Compounds,” Phosphorus Sulfur Silicon 192, no. 3 (2017): 307–15.
   Web of Science ®Google Scholar
• H. Ozay, M. Yildirim, and O. T. Ozay, “Synthesis and Characterization of Novel Urea and Thiourea Substitute Cyclotriphosphazene Compounds as Naked-Eye Sensors for F − and CN − Anions,” Journal of Chemistry. 39 (2015): 777–88.
   Web of Science ®Google Scholar
• M. K. Chahal, T. A. Dar, and M. Sankar, “Facile Synthesis of Functionalized Urea, Imidazolium Salt, Azide, and Triazole from a 2-Amino-5,7-Dimethyl-1,8-Naphthyridine Scaffold and Their Utilization in Fluoride Ion Sensing,” New Journal of Chemistry 42, no. 12 (2018): 10059–66.
   Web of Science ®Google Scholar
• W. Li, Q. Xu, Y. Li, W. Zhu, J. Cui, Y. Ju, and G. Li, “Neutral Bile Acid Cyclic Dimers Exhibit Fluoride Coordination by Cooperative Aliphatic and Triazole CH Segments,” Tetrahedron Letters. 54, no. 29 (2013): 3868–71.
   Web of Science ®Google Scholar
• P. Rani, K. Lal, R. Shrivastava, and V. D. Ghule, “Synthesis and Characterization of 1,2,3-Triazoles-Linked Urea Hybrid Sensor for Selective Sensing of Fluoride Ion,” Journal of Molecular Structures 1203 (2020): 127437–42.
   Web of Science ®Google Scholar
• Q.-Y. Chen, and C.-F. Chen, “A New Fluorescent as Well as Chromogenic Chemosensor for Anions Based on an Anthracene Carbamate Derivative,” Tetrahedron Letters 45, no. 34 (2004): 6493–6.
   Web of Science ®Google Scholar
• X. Zhang, S. Lee, Y. Liu, M. Lee, J. Yin, and J. L. Sessler, Journal of Yoon Science and Report 4 (2004): 4593–600.
   Google Scholar
• R. M. Duke, E. B. Veale, F. M. Pfeffer, P. E. Kruger, and T. Gunnlaugsson, “Colorimetric and Fluorescent Anion Sensors: An Overview of Recent Developments in the Use of 1,8-Naphthalimide-Based Chemosensors,” Chemical Society Reviews 39, no. 10 (2010): 3936–53.
   PubMed Web of Science ®Google Scholar
• Kashmiri Lal, Nisha Poonia, Poonam Rani, Ashwani Kumar, and Anil Kumar, “Synthesis, Antimicrobial Evaluation and Docking Studies of Urea-Triazole-Amide Hybrids,” Journal of Molecular Structure 1215 (2020): 128234–44.
   Web of Science ®Google Scholar
• Shilin Xu, Xiaoxi Zhuang, Xiaofen Pan, Zhang Zhang, Lei Duan, Yingxue Liu, Lianwen Zhang, Xiaomei Ren, and Ke Ding, “1-Phenyl-4-Benzoyl-1H-1,2,3-Triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α,” Journal of Medicinal Chemistry 56, no. 11 (2013): 4631–40.
   PubMed Web of Science ®Google Scholar
• N. Iqbal, S. Abid Ali, I. Munir, S. Khan, K. Ayub, M. Al-Rashida, M. Islam, Z. Shafiq, R. Ludwig, and A. Hameed, “Acridinedione as Selective Flouride Ion Chemosensor: A Detailed Spectroscopic and Quantum Mechanical Investigation,” RSC Advances 8, no. 4 (2018): 1993–2003.
   PubMed Web of Science ®Google Scholar
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, and M. A. Robb, Gaussian, “09, Revision E,” 01 (Wallingford, CT: Gaussian, Inc.; 2013).
   Google Scholar
• Xiaofeng Yang, Gege Zhang, Yexin Li, Zheng Liu, Xiaoqian Gong, Bin Gao, Guangyou Zhang, Yu Cui, and Guoxin Sun, “Colorimetric and Fluorogenic Signalling of Fluoride Ions by Diketopyrrolopyrrole-Based Chemosensor,” RSC Advances 5, no. 29 (2015): 22455–62.
   Web of Science ®Google Scholar