Delayed lanthanide luminescent Tb(III) complexes formed from lower rim amide functionalised calix[4]arenes

作者: Christophe Lincheneau , Eoin Quinlan , Jonathan A. Kitchen , Thomas McCabe , Susan E. Matthews

DOI: 10.1080/10610278.2013.810339

关键词:

摘要: The synthesis and the photophysical studies of a new generation time resolved luminescent systems based on calix[4]arenes alkylated at lower rim, capable hosting lanthanide (III) ions such as terbium sensitising its emission, are described. Two series ligands were designed to provide an ideal cavity host (Tb(III)) synthesised in high yields following two novel approaches. tetra-alkylation, which was achieved one step using with piperidino- morpholino-acetamide pendant arms, provides eight donor atoms forming binding ‘pocket’ distance from metal core favour sensitisation via antenna effect. Of ligand developed, compounds 3 4 possess short spacer between calix amide receptor site. second 6–7, longer 2 steps through ester analogue 5. crystal structure (and 6 shown Supporting Information, available o...

参考文章(14)
Emil M Georgiev, Joseph Clymire, Gary L McPherson, D Max Roundhill, Luminescent europium(III) and terbium(III) ions encapsulated in a 2-aminoethoxy or carbamoyloxy substituted calixarene host Inorganica Chimica Acta. ,vol. 227, pp. 293- 296 ,(1994) , 10.1016/S0020-1693(00)84023-2
Pascal Froidevaux, Jack M. Harrowfield, Alexander N. Sobolev, Calixarenes as scaffolds: introduction of tridentate rare earth metal binding units into calix[4]arene. Inorganic Chemistry. ,vol. 39, pp. 4678- 4687 ,(2000) , 10.1021/IC000353Z
Issam Oueslati, Rute A. Sá Ferreira, Luís D. Carlos, Carlos Baleizão, Mário N. Berberan-Santos, Baltazar de Castro, Jacques Vicens, Uwe Pischel, Calix[4]azacrowns as novel molecular scaffolds for the generation of visible and near-infrared lanthanide luminescence. Inorganic Chemistry. ,vol. 45, pp. 2652- 2660 ,(2006) , 10.1021/IC051159L
Nariaki Sato, Seiji Shinkai, Energy-transfer luminescence of lanthanide ions encapsulated in sensitizer-modified calix[4]arenes Journal of The Chemical Society-perkin Transactions 1. pp. 621- 624 ,(1993) , 10.1039/P29930000621
Koji Iwamoto, Seiji Shinkai, Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene Journal of Organic Chemistry. ,vol. 57, pp. 7066- 7073 ,(1992) , 10.1021/JO00052A016
Gilles Ulrich, Raymond Ziessel, Ilse Manet, Massimo Guardigli, Nanda Sabbatini, Franca Fraternali, Georges Wipff, Calix[4]Arene Podands and Barrelands Incorporating 2,2″‐Bipyridine Moieties and Their Lanthanide Complexes: Luminescence Properties Chemistry: A European Journal. ,vol. 3, pp. 1815- 1822 ,(1997) , 10.1002/CHEM.19970031114
Keisuke Ohto, Masayuki Yano, Katsutoshi Inoue, Takeshi Nagasaki, Masahiro Goto, Fumiyuki Nakashio, Seiji Shinkai, Effect of coexisting alkaline metal ions on the extraction selectivity of lanthanide ions with calixarene car☐ylate derivatives Polyhedron. ,vol. 16, pp. 1655- 1661 ,(1997) , 10.1016/S0277-5387(96)00470-6
Jennifer K. Molloy, Oxana Kotova, Robert D. Peacock, Thorfinnur Gunnlaugsson, Synthesis of luminescent homo-dinuclear cationic lanthanide cyclen complexes bearing amide pendant arms through the use of copper catalysed (1,3-Huisgen, CuAAC) click chemistry. Organic and Biomolecular Chemistry. ,vol. 10, pp. 314- 322 ,(2012) , 10.1039/C1OB06203D
Sebastiano Pappalardo, Francesco Bottino, Luigi Giunta, Marek Pietraszkiewicz, Jerzy Karpiuk, Photoactive Eu(III) and Tb(III) complexes of calix[4]arenes with pyridine- N -oxide pendant groups Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 10, pp. 387- 392 ,(1991) , 10.1007/BF01133323
Daniel D'Alessio, Sara Muzzioli, Brian W. Skelton, Stefano Stagni, Massimiliano Massi, Mark I. Ogden, Luminescent lanthanoid complexes of a tetrazole-functionalised calix[4]arene Dalton Transactions. ,vol. 41, pp. 4736- 4739 ,(2012) , 10.1039/C2DT12246D