Near infrared (NIR) lanthanide emissive langmuir-blodgett monolayers formed using Nd(III) directed self-assembly synthesis of chiral amphiphilic ligands

Langmuir

Volumn 29, Issue 36, 2013, Pages 11506-11515

  Barry, Dawn E ^a   Kitchen, Jonathan A ^a,d   Albrecht, Martin ^b   Faulkner, Stephen ^c   Gunnlaugsson, Thorfinnur ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CIRCULAR DICHROISM SPECTRA; DIRECTED SELF-ASSEMBLY; EFFICIENT ENERGY TRANSFER; EXCITED STATE LIFETIMES; LANGMUIR-BLODGETT MONOLAYERS; LANTHANIDE LUMINESCENCE; PHOTOPHYSICAL PROPERTIES; SURFACE PRESSURE-AREA;

CHROMOPHORES; ENERGY TRANSFER; EXCITED STATES; INFRARED DEVICES; INTERFACE STATES; INTERFACES (MATERIALS); LANGMUIR BLODGETT FILMS; LANTHANUM COMPOUNDS; MONOLAYERS; NUCLEAR PHYSICS; QUARTZ; RARE EARTH ELEMENTS; SELF ASSEMBLY; SURFACE CHEMISTRY;

LIGANDS;

LANTHANIDE; LIGAND; NEODYMIUM;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; INFRARED RADIATION; STEREOISOMERISM;

HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INFRARED RAYS; LANTHANOID SERIES ELEMENTS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEODYMIUM; STEREOISOMERISM;

EID: 84884190798     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la402274s     Document Type: Article

References (41)

1. Binnemans, K. Lanthanide-based Luminescenct Hybrid Materials Chem. Rev. 2009, 109, 4283
2. Faulkner, S.; Natrajan, L. S.; Perry, W. S.; Sykes, D. Sensitised luminescence in lanthanide containing arrays and d-f hybrids Dalton Trans. 2009, 3890
3. Bunzli, J.-C. G.; Piguet, C. Taking advantage of luminescent lanthanide ions Chem. Soc. Rev. 2005, 34, 1048
4. Lincheneau, C.; Stomeo, F.; Comby, S.; Gunnlaugsson, T. Recent Highlights in the use of Lanthanide-directed Synthesis of Novel Supramolecular (Luminescent) Self-assembly Structures such as Coordination Bundles, Helicates and Sensors Aust. J. Chem. 2011, 64, 1315
5. Pandya, S.; Yu, J.; Parker, D. Engineering emissive lanthanide complexes for molecular imaging and sensing Dalton Trans. 2006, 2757
6. Eliseeva, S. V.; Bunzli, J.-C. G. Lanthanide luminescence for functional materials and bio-sciences Chem. Soc. Rev. 2010, 39, 189
7. Bunzli, J.-C. G. Lanthanide Luminescence for Biomedical Analyses and Imaging Chem. Rev. 2010, 110, 2729
8. Comby, S.; Bünzli, J.-C. G. Lanthanide Near-Infrared Luminescence in Molecular Probes and Devices. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Jr.; Bünzli, J.-C. G.; Pecharsky, V. K., Eds.; Elsevier Science B.V.: Amsterdam, 2007; Vol. 37, Ch. 235, pp 217-470.
9. Ward, M. D. Mechanisms of sensitization of lanthanide(III)-based luminescence in transition metal/lanthanide and anthracene/lanthanide dyads Coord. Chem. Rev 2010, 254, 2634
10. de Bettencourt-Dias, A. Lanthanide-based emitting materials in light-emitting diodes Dalton Trans. 2007, 2229-2241
11. Aboshyan-Sorgho, L.; Besnard, C.; Pattison, P.; Kittilstved, K. R.; Aebischer, A.; Bunzli, J.-C. G.; Hauser, A.; Piguet, C. Near-Infrared-Visible Light Upconversion in a Molecular Trinuclear d-f-d Complex Angew. Chem., Int. Ed. 2011, 50, 4108
12. Beeby, A.; Burton-Pye, B. P.; Faulkner, S.; Motson, G. R.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D. Synthesis and near-IR luminescence properties of neodymium(III) and ytterbium(III) complexes with poly(pyrazolyl) borate ligands Dalton Trans. 2002, 1923
13. Binnemans, K.; Gorller-Walrand, C. Lanthanide-containing liquid crystals and surfactants Chem. Rev. 2002, 102, 2303-2345
14. Bunzli, J. C. G.; Piguet, C. Lanthanide-containing molecular and supramolecular polymetallic functional assemblies Chem. Rev. 2002, 102, 1897-1928
15. Torelli, S.; Imbert, D.; Cantuel, M.; Bernardinelli, G.; Delahaye, S.; Hauser, A.; Bunzli, J. C. G. Piguet, Tuning the decay time of lanthanide-based near infrared luminescence from micro- to milliseconds through d -> f energy transfer in discrete heterobimetallic complexes, C Chem.-Eur. J. 2005, 11, 3228-3242
16. Wada, Y.; Okubo, T.; Ryo, M.; Nakazawa, T.; Hasegawa, Y.; Yanagida, S. High efficiency near-IR emission of Nd(III) based on low-vibrational environment in cages of nanosized zeolites J. Am. Chem. Soc. 2000, 122, 8583
17. 3+ in liquid media Coord. Chem. Rev. 1998, 461
18. Pope, S. J. A.; Coe, B. J.; Faulkner, S.; Bichenkova, E. V.; Yu, X.; Douglas, K. T. Self-Assembly of Heterobimetallic d-f Hybrid Complexes: Sensitization of Lanthanide Luminescence by d-Block Metal-to-Ligand Charge-Transfer Excited States J. Am. Chem. Soc. 2004, 126, 9490
19. Perry, W. S.; Pope, S. J. A.; Allain, C.; Coe, B. J.; Kenwright, A. M.; Faulkner, S. Synthesis and photophysical properties of kinetically stable complexes containing a lanthanide ion and a transition metal antenna group Dalton Trans. 2010, 39, 10974
20. 3 Coordination Complexes Possessing Improved Near-Infrared (NIR) Lanthanide Luminescent Properties in Aqueous Solution Inorg. Chem. 2010, 49, 8449
21. Lehr, J.; Bennett, J.; Tropiano, M.; Sørensen, T. J.; Faulkner, S.; Beer, P. D.; Davis, J. J. Reversible recruitment and emission of DO3A-derived lanthanide complexes at ligating molecular films on gold Langmuir 2013, 29, 1475
22. Truman, L. K.; Comby, S.; Gunnlaugsson, T. pH-Responsive Luminescent Lanthanide-Functionalized Gold Nanoparticles with On-Off Ytterbium Switchable Near-Infrared Emission Angew. Chem., Int. Ed. 2012, 51, 9624
23. Stomeo, F.; Plush, S. E.; Gunnlaugsson, T. Soft Matter pH Sensing: From Luminescent Lanthanide pH Switches in Solution to Sensing in Hydrogels Chem. Mater. 2006, 18, 4336
24. Similar work has also been developed by: Qiao, Y.; Lin, Y. Y.; Zhang, S. F.; Huang, J. B. Lanthanide-Containing Photoluminescent Materials: From Hybrid Hydrogel to Inorganic Nanotubes Chem.-Eur. J. 2011, 17, 5180-5187
25. Massue, J.; Quinn, S. J.; Gunnlaugsson, T. Lanthanide luminescent displacement assays: The sensing of phosphate anions using Eu(III)-cyclen- conjugated gold nanoparticles in aqueous solution J. Am. Chem. Soc. 2008, 130, 6900
26. Bonnet, C. S.; Massue, J.; Quinn, S. J.; Gunnlaugsson, T. Lanthanide luminescent gold nanoparticles: pH-driven self-assembly formation between Eu(III)-cyclen conjugated AuNPs and sensitising beta-diketonate antenna in water Org. Biomol. Chem. 2009, 3074
27. Similar work has also been developed by: Stasiuk, G. J; Tamang, S.; Imbert, D.; Poillot, C.; Giardiello, M.; Tisseyre, C.; Barbier, E. L.; Fries, P. H.; de Waard, M.; Reiss, P.; Mazzanti, M. Cell-Permeable Ln(III) Chelate-Functionalized InP Quantum Dots As Multimodal Imaging Agents ACS Nano 2011, 5, 8193-8201
28. Kitchen, J. A.; Barry, D. E.; Mercs, L.; Albrecht, M.; Peacock, R. D.; Gunnlaugsson, T. Circularly Polarized Lanthanide Luminescence from Langmuir-Blodgett Films Formed from Optically Active and Amphiphilic EuIII-Based Self-Assembly Complexes Angew. Chem., Int. Ed 2012, 51, 704
29. Cosier, J.; Glazer, A. M. A nitrogen gas stream cryostat for general X-ray diffraction studies J. Appl. Crystallogr. 1986, 19, 105
30. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode Methods Enzymol. 1997, 276
31. Sheldrick, G. M. A short history of SHELX Acta Crystallogr., Sect. A 2008, A64, 112
32. Dickins, R. S.; Howard, J. A. K.; Maupin, C. L.; Maloney, J. M.; Parker, D.; Peacock, R. D.; Riehl, J. P.; Siligard, G. Ground and excited state chiroptical properties of enantiopure macrocyclic tetranaphthyl lanthanide complexes: controlled modulation of the frequency and polarisation of emitted light New J. Chem. 1998, 891
33. Satrijo, A.; Meskers, S. C. J.; Swager, T. M. Probing a Conjugated Polymer's Transfer of Organization-Dependent Properties from Solutions to Films J. Am. Chem. Soc. 2006, 128, 9030
34. Similarly others have seen this effect: Andreiadis, E. S.; Imbert, D.; Pecaut, J.; Demadrille, R.; Mazzanti, M. Self-assembly of highly luminescent lanthanide complexes promoted by pyridine-tetrazolate ligands Dalton Trans. 2012, 41, 1268-1277
35. We have also seen such effect in double stranded dimetallic helicate formations: Stomeo, F.; Lincheneau, C.; Leonard, J. P.; O'Brien, J. E.; Peacock, R. D.; McCoy, C. P.; Gunnlaugsson, T. Metal-Directed Synthesis of Enantiomerially Pure Dimetallic Lanthanide Luminescent Triple-Stranded Helicates J. Am. Chem. Soc. 2009, 131, 9636
36. Examples of visibly emitting lanthanide based LB films include: Xu, B.; Zhu, H.-X.; Yan, B. Novel Langmuir-Blodgett film with ternary europium complex of long chain mono-eicosyl cis-butene dicarboxylate and 1,10-phenanthroline: Cooperative assembly and luminescence Inorg. Chem. Commun. 2010, 13, 448 (and reference therein).
37. Qian, D.-J.; Yang, K.-Z.; Nakahara, H.; Fukuda, K. Monolayers of Europium Complexes with Different Long Chains and β-Diketonate Ligands and Their Emission Properties in Langmuir-Blodgett Films Langmuir 1997, 13, 5925 (and references therein).
38. Dutton, P. J.; Conte, L. Terbium Luminescence in Langmuir-Blodgett Films of Octafunctionalized Calix[4]resorcinarenes Langmuir 1999, 15, 613
39. Gao, L.-H.; Wang, K.-Z.; Cai, L.; Zhang, H.-Z.; Jin, L.-P.; Huang, C.-H.; Gao, H.-J. Studies of Langmuir-Blodgett Films of an Ion Pair Metal Complex Containing Eu(III)-Ru(II) Dual Chromophores J. Phys. Chem. B 2006, 110, 7402 (and references therein).
40. Matsumoto and co-workers have recently shown that NIR emissive lanthanide doped nanoparticles can be dip-coded onto plastic sheets: Watanabe, S.; Hyodo, H.; Taguchi, H.; Soga, K.; Takanashi, Y.; Matsumoto, M. J. Oleo Sci. 2012, 61, 565-573
41. Hauser, C. P.; Thielemann, D. T.; Adlung, M.; Wickleder, C.; Roesky, P. W.; Weiss, C. K.; Landfester, K. Luminescent Polymeric Dispersions and Films Based on Oligonuclear Lanthanide Clusters Macromol. Chem. Phys. 2011, 212, 286-296