ISMSC 2007 - Università degli Studi di Pavia

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PSB 95 Photoresponsive Malachite Green Derivative and Photoinduced Vesicle Fusion Ryoko M. Uda a , Keiichi Kimura b a Department of Chemical Engineering, Nara National College of Technology, Yata 22, Yamatokoriyama, Nara 639-1080, Japan b Department of Applied Chemistry, Faculty of Systems Engineering, Wakayama University, Sakae-dani 930, Wakayama 640-8510, Japan Amphiphiles contain hydrophilic and hydrophobic moieties and spontaneously form assemblies in aqueous media. Control of molecular assembling can be achieved by shifting the balance of hydrophobicity and hydrophilicity. Amphiphiles containing a photochromic moiety can undergo conformational and electronic changes upon photoirradiation, offering an attractive modulation of assemblies. We have designed a Malachite Green derivative carrying a long alkyl chain (Fig. 1). The Malachite Green derivative, when ionized photochemically, exhibits hydrophilicity by its triphenylmethyl cation and hydrophobicity by its long alkyl chain. Consequently, the long-alkylchain Malachite Green generates an amphiphilicity on the lipophilic compound by photoirradiation. The photogenerated electrical charge on the head group is expected to provide assemblies with a drastic effect. Actually, we have observed significant changes induced by the long-alkyl-chain Malachite Green in the critical micelle concentration and the solubility of oily substance into micelle solution 1,2 . O H3C CH3 N Here we present the photoinduced structural change in vesicles containing the long-alkyl-chain Malachite Green derivative. The Malachite Green derivative is embedded in the vesicle bilayer consisting of cationic and anionic surfactants. Photoirradiation on the Malachite Green derivative destabilizes the vesicle bilayer, resulting vesicle fusion (Fig. 2). We discuss the photoinduced vesicle fusion by fluorescence analysis and transmission electron microscopy. [1] R. M. Uda, M. Oue, K. Kimura, Chem. Lett., 2004, 33, 586-587. [2] R. M. Uda, K. Kimura, Bull. Chem. Soc. Jpn., 2005, 78, 1862-1867. C CN N H3C CH3 UV Heat Hydrophobic group Hydrophiric group H3C N CH3 O C+ + CN - N CH3 H3C Figure 1. Photo-generated amphiphilicity on the long-alkyl-chain Malachite Green derivative. Malachite Green derivative UV Generated amphiphilicity Bilayer destabilization Vesicle fusion Figure 2. Conceptual represetion of photoinduced bilayer destabilization and subsequent vesicle fusion Stable terbium probes highly luminescent in aqueous solutions : macrocyclic ligands derived from N,C-pyrazolylpyridine Isabelle Nasso, C. Galaup, B. Mestre, C. Picard Laboratoire de Synthèse et Physicochimie de Molécules d’Intérêt Biologique, CNRS UMR 5068, Université Paul Sabatier, 31062 Toulouse cedex 09, France Some organic ligands can act as light collectors (antenna) transferring intra-molecularly the excitation energy to the lanthanide ion (emitter), yielding highly luminescent lanthanide complexes. [1] Eu(III) systems working in aqueous solutions are widely used for time-resolved measurements in high throughput assays (clinical diagnostic assays or drug development) or fluorescence microscopy. [2] Recently, we reported the efficient sensitization of Tb(III) ion by an open chain polyaminocarboxylate ligand based on the N,C-pyrazolylpyridine chromophore as antenna (compound 1). [3] Here we present the synthesis of new macrocyclic ligands based on this chromophoric unit (compounds 2-4), and the luminescence properties of the corresponding Tb(III) complexes. 1 N N N N HO2C CO2H HO2C 2 HO 2C N N N N N N CO 2H N CO 2H CO 2H R N N N HO 2C N N 3, R = H N N 4, R = COOH CO 2H CO 2H PSB 96 These complexes are highly luminescent in aqueous solution: the decays of the Tb( 5 D4) luminescence are long lived ( 1.70 ms) and high quantum yield ( 40 %) were obtained following excitation of the -* state of the pyrazolylpyridine unit. The photophysical properties of these complexes will be discussed with regard of the mechanism of the ligand-to-metal energy transfer process and will be compared with those derived from 2,2’-bipyridine analogues. Their kinetic stability in aqueous solutions will also be reported. [1] P. G. Sammes and G. Yahogliou, Nat. Prod. Rep., 1996, 13, 1-28. [2] I. Hemmila and V. Laitala, J. Fluorescence, 2005, 15, 529-542. [3] C. Picard, N. Geum, I. Nasso, B. Mestre, P. Tisnès, S. Laurent, L. Vander Elst, Bioorg. Med. Chem. Lett., 2006, 16, 5309-5312.
PSB 97 Development of innovative sol-gel coatings for solid phase microextraction based on quinoxaline-bridged cavitands Paolo Betti a , Federica Bianchi b , Franco Bisceglie b , Enrico Dalcanale a , Monica Mattarozzi b a Dipartimento di Chimica Organica ed Industriale, Università di Parma, Viale G.P. Usberti 17/A, 43100 Parma, Italy b Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università di Parma, Viale G.P. Usberti 17/A, 43100 Parma, Italy A problem of paramount importance in the field of analytical chemistry is related to the development of innovative materials to be used as new devices both in the separation field and for sample preparation techniques, thus enhancing the selectivity as well as the overall performances of the system under investigation with regard to target analytes or specific classes of compounds. In particular, the use of innovative materials, capable of highly selective interactions with the analytes (avoiding co-extraction of interferents from the matrix), turns out particularly interesting in all those cases in which commercially available materials do not allow an adequate extraction of the compounds under investigation. As far solid phase microextraction (SPME) is concerned, the major challenge is to improve the capabilities of this technique by developing novel coatings characterised by high thermal, chemical and pH stability. New technologies are required in order to obtain chemically bonded materials onto the silica surface. Sol-gel technology [1] has been recently proposed as innovative alternative to the commonly utilized grafting procedures owing to its capabilities of producing a great variety of inorganic networks from silicon or metal alkoxide monomer precursors under mild conditions. In this study, cavitands are proposed as supramolecular receptors in order to develop materials characterized by high selectivity for the sampling of toxic compounds [2]. Owing to the capabilities of providing specific interactions with target analytes, quinoxaline-based cavitands have been properly tuned up and introduced in a sol-gel process, thus producing highly stable and selective materials to be used as trapping devices for volatile organic compounds. [1] O. Lev, Anal. Chem, 1995, 67, 22A–30A [2] F:Bianchi, R. Pinalli, F. Ugozzoli, S. Spera, M. Careri, E. Dalcanale, New J. Chem., 2003, 27, 502–509
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nd International Symposium on Macro
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Eric Anslyn University of Texas at
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1 Map of Salice Terme 7 5 6 3 9 2 8
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Symposium Program All sessions will
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11:40 - 12:00 Oral Presentation: V.
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PSA 22 Anion Receptors Based On The
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PSA 72 Molecular Tectonics: STM Stu
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PSB 11 Dual binding properties of p
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PSB 57 Removal Of Heavy Metal Ions
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40 years of polyazamacrocycles. A p
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PL 5 Anion-Templated Assembly of In
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Exercising Demons: Synthetic Molecu
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Synthetic Strategies and Structural
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Anion binding as a conformational a
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Supramolecular control of a metal c
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OP 3 Control of molecular architect
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Catalyst discovery using dynamic co
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Cucurbit[n]uril Molecular Container
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OP 15 From non-mesomorphic nature t
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OP 19 Pyrrolic Tripodal Receptors f
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PSA 1 Efficient synthesis of pseudo
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Tetra-Cationic phthalocyanines Yasi
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PSA 9 Cell penetrating borosilica n
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PSA 13 Halide anion interactions wi
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Sensing with cavitands: Moving from
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Lead(II) complexation by calix[4]-h
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Functional [2×2] Grids Xiao-Yu Cao
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Neutral supramolecular systems inco
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PSA 33 Ratiometric Ion Sensors by R
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A photocontrollable receptor for Cu
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New emitters for mass spectrometric
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PSA 45 A fast-moving electrochemica
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Macrocyclic Porphyrin-Bidentate Che
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PSA 53 Electronic spectroscopy of e
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PSA 57 Self-assembly of calixarene/
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PSA 61 Piperazine Containing Polyam
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PSA 65 Synthesis of Self-Assembly S
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PSA 69 Assembly of Metallomacrocycl
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Supra-Biomolecular Tandem Assays -
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PSA 77 Synthesis and molecular reco
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PSA 81 Reaction of phthalic aldehyd
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Binding of perrhenate and pertechne
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Page 93 and 94: PSB 9 A Quantitative [2]Rotaxane Sy
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Page 101 and 102: PSB 25 A Minimalist Design for Self
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Page 105 and 106: PSB 33 Multinuclear NMR, ESI MS and
Page 107 and 108: PSB 37 New Anthracene-based cycloph
Page 109 and 110: PSB 41 1,3,5-Tris(2-aminophenyl)ben
Page 111 and 112: Simple Isophthalamide Derivatives A
Page 113 and 114: PSB 49 On Sokolov’s approach to a
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Page 117 and 118: PSB 57 Removal of heavy metal ions
Page 119 and 120: PSB 61 Molecular Recognition of Ele
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ISMSC 2007 - Università degli Studi di Pavia

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