Helicenoid-based bis-1,2,3-triazole tweezer: Synthesis and selective iodide sensing

References

• Brunel, J. M.BINOL: A Versatile Chiral Reagent. Chem. Rev.2005, 105, 857-897. DOI: 10.1021/cr040079g.
   PubMed Web of Science ®Google Scholar
• Sundar, M. S.; Talele, H. R.; Mande, H. M.; Bedekar, A. V.; Tovar, R. C.; Muller, G.Synthesis of Enantiomerically Pure Helicene like Bis-Oxazines Fromatropisomeric 7,7’-Dihydroxy BINOL: Preliminary Measurements of the Circularly Polarized Luminescence. Tetrahedron Lett.2014, 55, 1760-1764. DOI: 10.1016/j.tetlet.2014.01.108.
   PubMed Web of Science ®Google Scholar
• (a) Gingras, M.One Hundred Years of Helicenes Chemistry. Part 3: Applications and Properties of Carbohe-Licenes. Chem. Soc. Rev.2013, 42, 1051-1095. DOI: 10.1039/C2CS35134J.;
   PubMed Web of Science ®Google Scholar
  (b) Shen, Y.; Chen, C. F.Helicenes: Synthesis and Applications. Chem. Rev.2012, 112, 1463-1535. DOI: 10.1021/cr200087r.
   PubMed Web of Science ®Google Scholar
• (a) Hou, J.-T.; Zhang, Q.-F.; Xu, B.-Y.; Lu, Q.-S.; Liu, Q.; Zhang, J.; Yu, X.-Q.A Novel BINOL Based Cyclophane via Click Chemistry: Synthesis and Its Applications for Sensing Silver Ions. Tetrahedron Lett.2011, 52, 4927-4930. DOI: 10.1016/j.tetlet.2011.07.050.;
   Web of Science ®Google Scholar
  (b) Chang, K.-C.; Su, I.-H.; Lee, G.-H.; Chung, W.-S.Triazole- and Azo-Coupled Calix[4]Arene as a Highly Sensitive Chromogenic Sensor for Ca2+ and Pb2+Ions. Tetrahedron Lett.2007, 48, 7274-7278. DOI: 10.1016/j.tetlet.2007.08.045.;
   Web of Science ®Google Scholar
  (c) Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J.A Pyrenyl-Appended Triazole-Based Calix [4] Arene as a Fluorescent Sensor for Cd2+and Zn2+. J. Org. Chem.2008, 73, 8212-8218. DOI: 10.1021/jo8012918.;
   PubMed Web of Science ®Google Scholar
  (d) Wu, W.; Li, B.; Gu, C.; Wang, J.; Singh, A.; Kumar, A.Luminescent Sensing of Cu2+, CrO42− and Photocatalytic Degradation of Methyl Violet by Zn(II) Metal-Organic Framework (MOF) Having 5,5′-(1H-2,3,5-Triazole-1,4diyl)Diisophthalic Acid Ligand. J. Mol. Struct. 2017, 1148, 531-536. molstruc. 2017.07.083. DOI: 10.1016/j.molstruc.2017.07.083.;
   Web of Science ®Google Scholar
  (e) Wang, W.; Yuan, W.-J.; Liu, Q.-L.; Lei, Y.-N.; Qi, S.; Gao, Y.Selective Fluorescence Sensor for Cu2+ with a Novel Triazole Schiff-Base Derivative with Coumarin Units. Heterocyc. Commun.2014, 20, 289-292. DOI: 10.1515/hc-2014-0117.;
   Web of Science ®Google Scholar
  (f) Otón, F.; González, M. d-C.; Espinosa, A.; Tárraga, A.; Molina, P.Synthesis, Structural Characterization, and Sensing Properties of Clickable Unsymmetrical 1,1′-Disubstituted Ferrocene Triazoles Derivatives. Organometallics2012, 31, 2085-2096. DOI: 10.1021/om300093c.;
   Web of Science ®Google Scholar
  (g) Huang, S.; Clark, R. J.; Zhu, L.Highly Sensitive Fluorescent Probes for Zinc Ion Based on Triazolyl-Containing Tetradentate Coordination Motifs. Org. Lett.2007, 9, 4999-5002. DOI: 10.1021/ol702208y.
   PubMed Web of Science ®Google Scholar
• (a) Nayal, A.; Kumar, A.; Chhatra, R. K.; Pandey, P. S.Dual Colorimetric Sensing of Mercury and Iodide Ions by Steroidal 1,2,3-Triazole-Stabilized Silver Nanoparticles. RSC Adv.2014, 4, 39866-39869. DOI: 10.1039/C4RA08080G.;
   Web of Science ®Google Scholar
  (b) Ghosh, K.; Kar, D.; Joardar, S.; Samadder, A.; Rahaman, A.Azaindole-1,2,3-Triazole Conjugate in a Tripod for Selective Sensing of Cl−, H2PO4− and ATP under Different Condition. RSC Adv.2014, 4, 11590-11597. DOI: 10.1039/c3ra45018j.;
   Web of Science ®Google Scholar
  (c) Kumar, A.; Chhatra, R. K.; Pandey, P. S.Synthesis of Click Bile Acid Polymers and Their Application in Stabilization of Silver Nanopa-Rticles Showing Iodide Sensing Property. Org. Lett.2010, 12, 24-27. DOI: 10.1021/ol902351g.;
   PubMed Web of Science ®Google Scholar
  (d) Caricato, M.; Olmo, A.; Gargiulli, C.; Gattuso, G.; Pasini, D.A ‘Clicked’ Macrocyclic Probe Incorporating Binol as the Signalling Unit for the Chiroptical Sensing of Anions. Tetrahedron2012, 68, 7861-7866. DOI: 10.1016/j.tet.2012.07.038.;
   Web of Science ®Google Scholar
  (e) Nayal, A.; Kumar, A.; Chhatra, R. K.; Pandey, P. S.Synthesis of a Bile Acid-Based Click-Macrocycle and Its Application in Selective Recognition of Chloride Ion. J. Org. Chem.2011, 76, 9086-9089. DOI: 10.1021/jo201161n.;
   PubMed Web of Science ®Google Scholar
  (f) Zahran, E. M.; Hua, Y.; Li, Y.; Flood, A. H.; Bachas, L. G.Triazolophanes: A New Class of Halide-Selective Iono-Phores for Potentiometric Sensor. Anal. Chem.2010, 82, 368-375. DOI: 10.1021/ac902132d.;
   PubMed Web of Science ®Google Scholar
  (g) Nayal, A.; Pandey, P. S.Bile Acid-Based Triazole and Triazolium Receptors for Colorimetric Sensing of Anions. Tetrahedron2015, 71, 6991-6996. DOI: 10.1016/j.tet.2015.07.006.
   Web of Science ®Google Scholar
• Wang, C.-Y.; Zou, J.-F.; Zheng, Z.-J.; Huang, W.-S.; Li, L.; Xu, L.-W.BINOL-Linked 1,2,3- Triazoles: An Unexpected Florescent Sensor with Anion-π Interaction for Iodide Ion. RSC Adv.2014, 4, 54256. DOI: 10.1039/C4RA09589H.
   Web of Science ®Google Scholar
• Zurro, M.; Mancheno, O. G.1,2,3-Triazole-Based Catalysts: From Metal- to Supramolecular Organic Catalysis. Chem. Rec. 2017, 17, 485-498. DOI: 10.1002/tcr.201600104.
   PubMed Web of Science ®Google Scholar
• (a) Hasan, M.; Khose, V. N.; Mori, T.; Borovkov, V.; Karnik, A. V.Sui Generis Helicene-Based Supramolecular Chirogenic System: Enantioselective Sensing, Solvent Control, and Application in Chiral Group Transfer Reaction. ACS Omega2017, 2, 592-598. DOI: 10.1021/acsomega.6b00522.;
   PubMed Web of Science ®Google Scholar
  (b) Hasan, M.; Borovkov, V.Helicene-Based Chiral Auxiliaries and Chirogenesis. Symmetry2018, 10, 1-48. DOI: 10.3390/sym10010010.
   Google Scholar
• Hasan, M.; Khose, V. N.; Pandey, A. D.; Borovkov, V.; Karnik, A. V.Tailor-Made Supramolecular Chirogenic System Based on Cs-Symmetric Rigid Organophosphoric Acid Host and Amino Alcohols: Mechanistic Studies. Org. Lett. 2016, 18, 440-443. DOI: 10.1021/acs.orglett.5b03477.
   PubMed Web of Science ®Google Scholar
• (a) Tornoe, C. W.; Christensen, C.; Meldal, M.Peptidotriazoles on Solid Phase: [1,2,3]-Trizole by Regiospecific Copper (I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem.2002, 67, 3057-3064. DOI: 10.1021/jo011148j.;
   PubMed Web of Science ®Google Scholar
  (b) Kolb, H. C.; Finn, M. G.; Sharp-Less, K. B.Click Chemistry: Diverse Chemical Function from a Few Good Reaction. Angew. Chem. Int. Ed.2001, 40, 2004-2021. DOI: 10.1002/1521-3773(20010601)40:10<2004::AID-ANTE2004>3.0.CO;2-5.
   PubMed Web of Science ®Google Scholar
• (a) Ho, H. A.; Leclerc, M. J.New Colorimetric and Fluorometric Chemosensor Based on a Cationic Polythiophene Derivative for Iodide-Specific Detection. J. Am. Chem. Soc.2003, 125, 4412-4413. DOI: 10.1021/ja028765p.;
   PubMed Web of Science ®Google Scholar
  (b) Vetrichelvan, M.; Nagarajan, R.; Valiyaveettil, S.Carbazole-Conta-Ining Conjugated Copolymers as Colorimetric/Fluorimetric Sensor for Iodide Anion. Macromolecules2006, 39, 8303-8310. DOI: 10.1021/ma0613537.
   Web of Science ®Google Scholar
• Bhatkalkar, S. G.; Kumar, D.; Ali, A.; Sachar, S.Surface Dynamics Associated with Zinc Oxide Nanoparticles and Biomolecules in Presence of Surfactants. J. Mol. Liq.2018, 268, 1-10. DOI: 10.1016/j.molliq.2018.07.037.
   Web of Science ®Google Scholar