Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
454
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and Characterization of Linear and Macrocyclic Ligands with Multiple Hemisalen Pockets

Pages 3177-3186 | Received 01 Apr 2011, Published online: 17 Aug 2012

REFERENCES

  • Liu , H.-B. ; Wang , M. ; Wang , Y. ; Wang , L. ; Sun , L.-C. Synthesis of tri- and disalicylaldehydes and their chiral Schiff base compounds . Synth. Commun. 2010 , 40 , 1074 – 1081 .
  • Leung , A. C. W. ; MacLachlan , M. J. Schiff base complexes in macromolecules . J. Inorg. Organomet. Polym. 2007 , 17 , 57 – 89 .
  • (a) Gallant , A. J. ; Hui , J. K.-H. ; Zahariev , F. E. ; Wang , Y. A. ; MacLachlan , M. J. Synthesis, structure, and computational studies of soluble conjugated multidentatemacrocycles . J. Org. Chem. 2005 , 70 , 7936 – 7946 ; (b) MacLachlan , M. J. Conjugated shape-persistent macrocycles via Schiff-base condensation: New motifs for supramolecular chemistry . Pure Appl. Chem. 2006 , 78 , 873 – 888 .
  • (a) Busch , D. H. Distinctive coordination chemistry and biological significance of complexes with macrocyclic ligands. Acc. Chem. Res. 1978, 11, 392–400; (b) Vigato , P. A. ; Tamburini , S. ; Bertolo , L. The development of compartmental macrocyclic Schiff bases and related polyamine derivatives. Coord. Chem. Rev. 2007, 251, 1311–1492; (c) Borisova , N. E. ; Reshetova , M. D. ; Ustynyuk , Y. A. Metal-free methods in the synthesis of macrocyclic Schiff bases. Chem. Rev. 2007, 107, 46–79.
  • (a) Haak , R. M. ; Martínez Belmonte , M. ; Escudero-Adán , E. C. ; Benet-Buchholza , J. ; Kleij , A. W. Olefin metathesis as a tool for multinuclear Co(III)salen catalyst construction: Access to cooperative catalysts . Dalton Trans. 2010 , 39 , 593 – 602 ; (b) Journaux , Y. ; Glaser , T. ; Steinfeld , G. ; Lozan , V. ; Kersting , B. Preparation and characterization of CrIII, MnII, FeII, CoII, and NiII complexes of a hexaazadithiophenolate macrocycle . Dalton Trans. 2006 , 1738 – 1748 ; (c) Kanesato , M. ; Houjou , H. ; Nagawa , Y. ; Hiratani , K. Synthesis and characterization of dinuclear lanthanide(III) and yttrium(III) cryptates of a hexavalent anionic polydentate ligand . Inorg. Chem. Commun. 2002 , 5 , 984 – 988 .
  • Gallant , A. J. ; Chong , J. H. ; MacLachlan , M. J. Heptametallic bowl-shaped complexes derived from conjugated Schiff-base macrocycles: Synthesis, characterization, and x-ray crystal structures . Inorg. Chem. 2006 , 45 , 5248 – 5250 .
  • (a) Yang , L.-L. ; Dang , Z.-H. ; Xu , L. Synthesis and crystal structure of a new complex {[CoIIIL2]·[CoII(H2O)6]0.5.2.25H2O}4 (H2 L˭N-(2-hydroxyphenyl)salicylidenimine) . Chin. J. Struct. Chem. 2009 , 28 , 493 – 497 ; (b) Dutta , S. ; Basu , P. ; Chakravorty , A. Mononuclear manganese(IV) in tridentate ONO coordination: Synthesis, structure, and redox regulation via oxygen donor variation . Inorg. Chem. 1991 , 30 , 4031 – 4037
  • Frischmann , P. D. ; Guieu , S. ; Tabeshi , R. ; MacLachlan , M. J. Columnar organization of head-to-tail self-assembled Pt4 rings . J. Am. Chem. Soc. 2010 , 132 , 7668 – 7675 .
  • Salassa , G. ; Castilla , A. M. ; Kleij , A. W. Cooperative self-assembly of a macrocyclic Schiff base complex . Dalton Trans. 2011 , 40 , 5236 – 5243 .
  • (a) Vigato , P. A. ; Tamburini , S. The challenge of cyclic and acyclic Schiff bases and related derivatives . Coord. Chem. Rev. 2004 , 248 , 1717 – 2128 ; (b) Hui , J. K.-H. ; MacLachlan , M. J. [6 + 6] Schiff-base macrocycles with 12 imines: Giant analogues of cyclohexane . Chem. Commun. 2006 , 2480 – 2482 .
  • (a) Guieu , S. ; Crane , A. K. ; MacLachlan , M. J. Campestarenes: Novel shape-persistent Schiff base macrocycles with five-fold symmetry . Chem. Commun. 2011 , 47 , 1169 – 1171 ; (b) Hartley , C. S. ; Moore , J. S. Programmed dynamic covalent assembly of unsymmetrical macrocycles . J. Am. Chem. Soc. 2007 , 129 , 11682 – 11683 ; (c) Fekner , T. ; Gallucci , J. ; Chan , M. K. Synthesis and metalation of a chiral, pyridine-strapped, cyclic bis(benzimidazole) ligand . Org. Lett. 2004 , 6 , 989 – 992 ; (d) Xu , X.-N. ; Wang , L. ; Wang , G.-T. ; Lin , J.-B. ; Li , G.-Y. ; Jiang , X.-K. ; Li , Z.-T. Hydrogen-bonding-mediated dynamic covalent synthesis of macrocycles and capsules: New receptors for aliphatic ammonium ions and the formation of pseudo[3]rotaxanes . Chem. Eur. J. 2009 , 15 , 5763 – 5774 .
  • Korich , A. L. ; Hughes , T. S. Arylene imine macrocycles of C3 h and C3 symmetry from reductive imination of nitroformylarene . Org. Lett. 2008 , 10 , 5405 – 5408 .
  • (a) Nartop , D. ; Gürkan , P. ; Sari , N. ; Çete , S. Tetradentate asymmetric Schiff bases and their Ni(II) and Fe(III) complexes . J. Coord. Chem. 2008 , 61 , 3516 – 3524 ; (b) Park , K. K. ; Oh , C. H. ; Joung , W. K. Sodium dithionite reduction of nitroarenes using viologen as an electron phase-transfert catalyst . Tetrahedron. Lett. 1993 , 34 , 7445 – 7446 .
  • Tzur , E. ; Ben-Asuly , A. ; Diesendruck , C. E. ; Goldberg , I. ; Lemcoff , N. G. Homodinuclear ruthenium catalysts for dimer ring-closing metathesis . Angew. Chem. Int. Ed. 2008 , 47 , 6422 – 6425 .
  • Minutolo , F. ; Bertini , S. ; Granchi , C. ; Marchitiello , T. ; Prota , G. ; Rapposelli , S. ; Tuccinardi , T. ; Martinelli , A. ; Gunther , J. R. ; Carlson , K. E. ; Katzenellenbogen , J. A. ; Macchia , M. Structural evolutions of salicylaldoximes as selective agonists for estrogen receptor β . J. Med. Chem. 2009 , 52 , 858 – 867 .
  • Manecke , G. ; Wille , W. E. Preparation and properties of chelate-forming monomeric and polymeric Schiff bases derived from salicylaldehyde and 2,5-dihydroxyterephthaldehyde . Makromol. Chem. 1970 , 133 , 61 – 82 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.