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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 10
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Articles

Terpyridinebenzaldehyde isomers: One-pot facile synthesis

Pages 1547-1555 | Received 16 Nov 2020, Published online: 22 Feb 2021

References

  • Chen, L.-J.; Yang, H.-B.; Shionoya, M. Chiral Metallosupramolecular Architectures. Chem. Soc. Rev. 2017, 46, 2555–2576. DOI: 10.1039/C7CS00173H.
  • Wu, G.-Y.; Chen, L.-J.; Xu, L.; Zhao, X.-L.; Yang, H.-B. Construction of Supramolecular Hexagonal Metallacycles via Coordination-Driven Self-Assembly: Structure, Properties and Application. Coord. Chem. Rev. 2018, 369, 39–75. DOI: 10.1016/j.ccr.2018.05.009.
  • Gan, M.-M.; Liu, J.-Q.; Zhang, L.; Wang, Y.-Y.; Hahn, F. E.; Han, Y.-F. Preparation and Post-Assembly Modification of Metallosupramolecular Assemblies from Poly(N-Heterocyclic Carbene) Ligands. Chem. Rev. 2018, 118, 9587–9641. DOI: 10.1021/acs.chemrev.8b00119.
  • Housecroft, C. E.; Constable, E. C. The Terpyridine Isomer Game: From Chelate to Coordination Network Building Block. Chem. Commun. 2020, 56, 10786–10794. DOI: 10.1039/d0cc04477f.
  • Chakraborty, S.; Newkome, G. R. Terpyridine-Based Metallosupramolecular Constructs: tailored Monomers to Precise 2D-Motifs and 3D-Metallocages. Chem. Soc. Rev. 2018, 47, 3991–4016. DOI: 10.1039/C8CS00030A.
  • Schwarz, G.; Haßlauer, I.; Kurth, D. G. From Terpyridine-Based Assemblies to Metallo-Supramolecular Polyelectrolytes (MEPEs). Adv. Colloid Interface Sci. 2014, 207, 107–120. DOI: 10.1016/j.cis.2013.12.010.
  • Song, B.; Kandapal, S.; Gu, J.; Zhang, K.; Reese, A.; Ying, Y.; Wang, L.; Wang, H.; Li, Y.; Wang, M.; et al. Self-Assembly of Polycyclic Supramolecules Using Linear Metal-Organic Ligands. Nat. Commun. 2018, 9, 4575–4583. DOI: 10.1038/s41467-018-07045-9.
  • Fu, J.-H.; Wang, S.-Y.; Chen, Y.-S.; Prusty, S.; Chan, Y.-T. One-Pot Self-Assembly of Stellated Metallosupramolecules from Multivalent and Complementary Terpyridine-Based Ligands. J. Am. Chem. Soc. 2019, 141, 16217–16221. DOI: 10.1021/jacs.9b08731.
  • Wang, S. ‐Y.; Huang, J. ‐Y.; Liang, Y. ‐P.; He, Y. J.; Chen, Y. ‐S.; Zhan, Y. ‐Y.; Hiraoka, S.; Liu, Y. ‐H.; Peng, S. ‐M.; Chan, Y. ‐T. Multicomponent Self-Assembly of Metallo-Supramolecular Macrocycles and Cages through Dynamic Heteroleptic Terpyridine Complexation. Chemistry 2018, 24, 9274–9284. DOI: 10.1002/chem.201801753.
  • Ziener, U.; Breuning, E.; Lehn, J.-M.; Wegelius, E.; Rissanen, K.; Baum, G.; Fenske, D.; Vaughan, G. Recognition‐Directed Supramolecular Assemblies of Metal Complexes of Terpyridine Derived Ligands with Self‐Complementary Hydrogen Bonding Sites. Chem. Eur. J. 2000, 6, 4132–4139. DOI: 10.1002/1521-3765(20001117)6:22<4132::AID-CHEM4132>3.0.CO;2-W.
  • Zhang, G.; Zeng, H.; Li, S.; Johnson, J.; Mo, Z.; Neary, M. C.; Zheng, S. 1-D Manganese(ii)-Terpyridine Coordination Polymers as Precatalysts for Hydrofunctionalisation of Carbonyl Compounds. Dalton Trans. 2020, 49, 2610–2615. DOI: 10.1039/C9DT04637B.
  • Kwong, H.-L.; Wong, W.-L.; Lee, W.-S.; Cheng, L.-S.; Wong, W.-T. New Chiral 2,2′:6′,2″-Terpyridine Ligands from the Chiral Pool: synthesis, Crystal Structure of a Rhodium Complex and Uses in Copper- and Rhodium-Catalyzed Enantioselective Cyclopropanation of Styrene. Tetrahedron Asymmetry 2001, 12, 2683–2694. DOI: 10.1016/S0957-4166(01)00431-1.
  • Zhang, Y.; Sun, X.; Zhang, H.; Zhao, J. Immobilization of Ru(Terpyridine)(2,6‐Pyridinedicarboxylate) onto MCM‐41 and Its Catalysis in the Oxidation of Alcohols. Appl. Organometal. Chem. 2016, 30, 645–652. DOI: 10.1002/aoc.3484.
  • Schofield, E. R.; Collin, J.-P.; Gruber, N.; Sauvage, J.-P. Photochemical and Thermal Ligand Exchange in a Ruthenium(ii) Complex Based on a Scorpionate Terpyridineligand. Chem. Commun. 2003, 188–189. DOI: 10.1039/b210607h.
  • Labra-Vázquez, P.; Bocé, M.; Tassé, M.; Mallet-Ladeira, S.; Lacroix, P. G.; Farfán, N.; Malfant, I. Malfant, I. Chemical and Photochemical Behavior of Ruthenium Nitrosyl Complexes with Terpyridine Ligands in Aqueous Media. Dalton Trans. 2020, 49, 3138–3154. DOI: 10.1039/C9DT04832D.
  • Jang, C. K.; Lee, Y. H.; Han, S. Y.; Jaung, J. Y. The Synthesis and Optical Characterization of Quinoxalines Bearing 2,2′:6′,2″-Terpyridine. Dyes Pigm. 2008, 79, 101–104. DOI: 10.1016/j.dyepig.2007.10.012.
  • Rajalakshmi, S.; Weyhermüller, T.; Dinesh, M.; Nair, B. U. Copper(II) Complexes of Terpyridine Derivatives: A Footstep towards Development of Antiproliferative Agent for Breast Cancer. J. Inorg. Biochem. 2012, 117, 48–59. DOI: 10.1016/j.jinorgbio.2012.08.010.
  • Liang, X.; Jiang, J.; Xue, X.; Huang, L.; Ding, X.; Nong, D.; Chen, H.; Pan, L.; Ma, Z. Synthesis, Characterization, Photoluminescence, anti-Tumor Activity, DFT Calculations and Molecular Docking with Proteins of Zinc(ii) Halogen Substituted Terpyridine Compounds. Dalton Trans. 2019, 48, 10488–10504. DOI: 10.1039/C8DT04924F.
  • Hahn, E. M.; Estrada-Ortiz, N.; Han, J.; Ferreira, V. F. C.; Kapp, T. G.; Correia, J. D. G.; Casini, A.; Kühn, F. E. Functionalization of Ruthenium(II) Terpyridine Complexes with Cyclic RGD Peptides to Target Integrin Receptors in Cancer Cells. Eur. J. Inorg. Chem. 2017, 2017, 1667–1672. DOI: 10.1002/ejic.201601094.
  • Robson, K. C. D.; Koivisto, B. D.; Yella, A.; Sporinova, B.; Nazeeruddin, M. K.; Baumgartner, T.; Grätzel, M.; Berlinguette, C. P. Design and Development of Functionalized Cyclometalated Ruthenium Chromophores for Light-Harvesting Applications. Inorg. Chem. 2011, 50, 5494–5508. DOI: 10.1021/ic200011m.
  • Ozawa, H.; Sugiura, T.; Kuroda, T.; Nozawa, K.; Arakawa, H. Highly Efficient Dye-Sensitized Solar Cells Based on a Ruthenium Sensitizer Bearing a Hexylthiophene Modified Terpyridine Ligand. J. Mater. Chem. A. 2016, 4, 1762–1770. DOI: 10.1039/C5TA10393B.
  • Caramori, S.; Husson, J.; Beley, M.; Bignozzi, C. A.; Argazzi, R.; Gros, P. C. Combination of Cobalt and Iron Polypyridine Complexes for Improving the Charge Separation and Collection in Ru(terpyridine)(2)-sensitised solar cells. Chemistry 2010, 16, 2611–2618. DOI: 10.1002/chem.200902761.
  • Duchanois, T.; Etienne, T.; Cebrián, C.; Liu, L.; Monari, A.; Beley, M.; Assfeld, X.; Haacke, S.; Gros, P. C. A. Iron‐Based Photosensitizer with Extended Excited‐State Lifetime: Photophysical and Photovoltaic Properties. Eur. J. Inorg. Chem. 2015, 2015, 2469–2477. DOI: 10.1002/ejic.201500142.
  • Ozawa, H.; Fukushima, K.; Urayama, A.; Arakawa, H. Efficient Ruthenium Sensitizer with an Extended π-Conjugated Terpyridine Ligand for Dye-Sensitized Solar Cells. Inorg. Chem. 2015, 54, 8887–8889. DOI: 10.1021/acs.inorgchem.5b01640.
  • Qian, C.; Qi, Q.-Y.; Jiang, G.-F.; Cui, F.-Z.; Tian, Y.; Zhao, X. Toward Covalent Organic Frameworks Bearing Three Different Kinds of Pores: The Strategy for Construction and COF-to-COF Transformation via Heterogeneous Linker Exchange. J. Am. Chem. Soc. 2017, 139, 6736–6743. DOI: 10.1021/jacs.7b02303.
  • Mastalerz, M. Porous Shape-Persistent Organic Cage Compounds of Different Size, Geometry, and Function. Acc. Chem. Res. 2018, 51, 2411–2422. DOI: 10.1021/acs.accounts.8b00298.
  • Greenaway, R. L.; Santolini, V.; Bennison, M. J.; Alston, B. M.; Pugh, C. J.; Little, M. A.; Miklitz, M.; Eden-Rump, E. G. B.; Clowes, R.; Shakil, A.; et al. High-Throughput Discovery of Organic Cages and Catenanes Using Computational Screening Fused with Robotic Synthesis. Nat. Commun. 2018, 9, 1–11. DOI: 10.1038/s41467-018-05271-9.
  • Chen, X.; Huang, N.; Gao, J.; Xu, H.; Xu, F.; Jiang, D. Towards Covalent Organic Frameworks with Predesignable and Aligned Open Docking Sites. Chem. Commun. 2014, 50, 6161–6163. DOI: 10.1039/C4CC01825G.
  • Goodall, W.; Wild, K.; Arm, K. J.; Williams, J. A. G. The Synthesis of 4′-Aryl Substituted Terpyridines by Suzuki Cross-Coupling Reactions: substituent Effects on Ligand Fluorescence. J. Chem. Soc., Perkin Trans. 2 2002, 1669–1681. DOI: 10.1039/B205330F.
  • Miyamoto, Y.; Kikuchi, A.; Iwahori, F.; Abe, J. Synthesis and Photochemical Properties of a Photochromic Iron(II) Complex of Hexaarylbiimidazole. J. Phys. Chem. A. 2005, 109, 10183–10188. DOI: 10.1021/jp0540306.
  • Filosa, A.; Wang, H.; Li, W.-J.; Zhang, W.; Ngo, E.; Piccolo, J. E.; Yang, H.-B.; Li, X. Order from Chaos: Self‐Assembly of Nanoprism from a Mixture of Tetratopic Terpyridine‐Porphyrin Conformers. Chin. J. Chem. 2019, 37, 1167–1173. DOI: 10.1002/cjoc.201900177.
  • Kröhnke, F. The Specific Synthesis of Pyridines and Oligopyridines. Synthesis. 1976, 1976, 1–24. DOI: 10.1055/s-1976-23941.
  • Heller, M.; Schubert, U. S. Functionalized 2,2'-Bipyridines and 2,2':6',2''-Terpyridines via Stille-Type Cross-Coupling Procedures. J. Org. Chem. 2002, 67, 8269–8272. DOI: 10.1021/jo0260600.
  • Cave, G. W. V.; Raston, C. L. Toward Benign Syntheses of Pyridines Involving Sequential Solvent Free Aldol and Michael Addition Reactions. Chem. Commun. 2000, 2199–2200. DOI: 10.1039/b007431o.
  • Wang, J.; Hanan, G. S. A Facile Route to Sterically Hindered and Non-Hindered 4′-Aryl-2,2′:6′,2′′-Terpyridines. Synlett. 2005, 2005, 1251–1254. DOI: 10.1055/s-2005-868481.
  • Rocco, D.; Housecroft, C. E.; Constable, E. C. Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong? Molecules. 2019, 24, 1799–1795. DOI: 10.3390/molecules24091799.
  • Achelle, S.; Malval, J.-P.; Aloïse, S.; Barsella, A.; Spangenberg, A.; Mager, L.; Akdas-Kilig, H.; Fillaut, J.-L.; Caro, B.; Robin-Le Guen, F. Synthesis, Photophysics and Nonlinear Optical Properties of Stilbenoid Pyrimidine-based Dyes Bearing Methylenepyran Donor Groups. Chemphyschem. 2013, 14, 2725–2736. DOI: 10.1002/cphc.201300419.
  • Chezal, J. M.; Moreau, E.; Desbois, N.; Blache, Y.; Chavignon, O.; Teulade, J. C. Synthesis of Carbamoylpyridine and Imidazo[1,5-a]Pyridin-1,3-Diones via Ortho-Acetalhydantoin Intermediates. Tetrahedron Lett. 2004, 45, 553–556. DOI: 10.1016/j.tetlet.2003.10.200.
  • Ueda, M.; Kawai, S.; Hayashi, M.; Naito, T.; Miyata, O. Efficient Entry into 2-Substituted Tetrahydroquinoline Systems through Alkylative Ring Expansion: Stereoselective Formal Synthesis of (+/–)-martinellic acid. J. Org. Chem. 2010, 75, 914–921. DOI: 10.1021/jo902540x.

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