LSO UMR6521 Handel

UMR 6521

Chimie, Electrochimie Moléculaires

Chimie Analytique

EQUIPE 2

Laboratory of Organic Chemistry Chimie et Physico-Chimie des Polyamines Cycliques et Linéaires

WELCOME...WELCOME...WELCOME...WELCOME...WELCOME...WELCOME...WELCOME...WELCOME...

SUMMARY

Research Area

Pr. Handel Presentation

Collaborators

Group Publications

Thesis

Album

Open Positions

Links

Group Homepage

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JESEC-PCL-2006

--18.09.07--

Organic Synthesis Laboratory Group

UMR-CNRS 6521 Faculte des Sciences et Techniques.

6, avenue Victor le Gorgeu.

C.S. 93837

29238 BREST Cedex 3

FRANCE

Tel.: 33 (0)2 98 01 61 38

Fax: 33 (0)2 98 01 65 94

Email Henri.Handel@univ-brest.fr

UMR 6521 Secretary:

Jacqueline L'helgouarch

Tel.: 33 (0)2 98 01 61 27
Fax: 33 (0)2 98 01 70 01
E-mail: Jacqueline.Lhelgouarch@univ-brest.fr

RESEARCH AREA

Our research works are concerned with the chemistry of cyclic polyamines, and more especially of tetraazamacrocycles. Our major aims are to propose new synthesis of tetraazamacrocycles and find new selective functionalization methods to get derivatives available for further applications. At last, our investigations deal with metal complexes.

keywords: tetraazamacrocycles; synthesis; mono N-functionalization; complexation.

We are presently developing new syntheses of cyclam, cyclen as well as of their precursors. Our approach consists in using linear-tetramine bis-aminals to get the start substrate in a stiff geometry favorable to cyclization.

keywords: bis-aminals; cyclization; cyclam; cyclen

Pr. Handel PRESENTATION

See the personnal Homepage.

COLLABORATORS

Professor	Homepage	Tel.	Office
Henri Handel	Click Here	33 (0)2 98 01 61 38	C123
Lecturers
Hélène Bernard		33 (0)2 98 01 66 44	C138
Michel Le Baccon (HDR)	Click Here	33 (0)2 98 01 64 97	C132
Nathalie Le Bris	Click Here	33 (0)2 98 01 66 44	C138
Véronique Patinec	Click Here	33 (0)2 98 01 79 27	C125
CNRS (CR)
Raphaël Tripier (HDR)	Click Here	33 (0)2 98 01 79 27	C125
Postdoc

Ph-D Students
Nicolas Bernier		33 (0)2 98 01 79 27	C125
Jean François Morfin		33 (0)2 98 01 61 39	C133bis
Anne-Sophie Delépine		33 (0)2 98 01 79 27	C125
Master M2





Exterior Collaborators
Pr. Michel Aplincourt	Reims (F)	GRECI
Pr. André Merbach	Lausanne (CH)	EPFL
Pr. P. Paoletti	Firenze (I)
Pr. V. Galasso	Trieste (I)
Pr. G. Serratrice	Grenoble	LEDSS

GROUP PUBLICATIONS (2001-2007)

- Stoichiometric mono N-functionalized cyclen via boron protected intermediate.
F. CHUBURU, M. LE BACCON, H. HANDEL.
Tetrahedron, 2001, 57, 2385.

- Bisaminals: efficient tools for bis-macrocycles synthesis
F. CHUBURU, M. LE BACCON, L. TOUPET, H. HANDEL, M. SOIBINET, I. DECHAMP-OLIVIER, J.-P. BARBIER, M. APLINCOURT. New J. Chem., 2001, 25, 1168.

- Basicity and coordination ability of linear hexa-amines in relation to N-(CH₂)_n-N chain link length. A solution study.
A. BENCINI, E. BERNI, F. CHUBURU, C. GIORGI, H. HANDEL, M. LE BACCON, P. PAOLETTI, B. VALTANCOLI.
Polyhedron, 2002, 21, 1459.

- On the structure and spectroscopic properties of the cis- and trans-isomers of cyclen-and cyclamglyoxal.
V. GALASSO, F. CHUBURU, H. HANDEL, M. LE BACCON, D. JONES.
J. Mol. Struct. – Theochem, 2002, 582, 187.

- Synthesis and NMR characterisation of new cyclam-glyoxal diamides.
M. ANTOINE, H. BERNARD, N. KERVAREC, H. HANDEL.
J. Chem. Soc. Perkin , 2002, 2, 552.

- Accelerating water exchange for Gd^III chelates by steric compression around the water binding site.
R. RULOFF, E. TOTH, R. SCOPELLITI, R. TRIPIER, H. HANDEL, A. MERBACH
J. Chem. Soc., Chem. Commun. 2002, 2630

- Unexpected conversion of 1,4,7,12-tetraazadodecane-glyoxal bisaminal to amidinium salt in acidic medium.
H. BERNARD, E. DEL RIO GARCIA, S. FEREC, N. KERVAREC, H. HANDEL
Eur. J. Org. Chem., 2003, 255

- Bis-aminals of linear tetraamines: kinetic and thermodynamic aspects of the condensation reaction.
F. CHUBURU, R. TRIPIER, M. LE BACCON, H. HANDEL.
Eur. J. Org. Chem., 2003, 1050

- XAS, ESR and potentiometric studies of three dinuclear N,N’ para-xylyl linked Bis-teraazamacrocycles Copper II Complexes.
M. SOIBINET, I. DECHAMP-OLIVIER, E. GUILLON, J.-P. BARBIER, M. APLINCOURT, F. CHUBURU, M. LE BACCON, H. HANDEL
Eur. J. Inorg. Chem, 2003, 1984

- Phenylglyoxal for polyamines modification and cyclam synthesis.
R. TRIPIER, F. CHUBURU, M. LE BACCON, H. HANDEL
Tetrahedron, 2003, 59, 4573

- A new versatile synthesis of macrotricyclic tetraazacycloalcane-based ligands from bis-aminal derivatives.

S. DEVELAY, R. TRIPIER, F. CHUBURU, M. LE BACCON, H. HANDEL

Eur. J. Chem. 2003, 3047

- Self-assembly route from a bis-aminal derivative to a new cyclam-based macropentacycle.

R. TRIPIER, S. DEVELAY, M. LE BACCON, F. CHUBURU, F. MICHAUD H. HANDEL

New J. Chem. 2004, 28, 2, 173-176.

- Powerful mono-N-alkylation of linear tetraamines via bis-aminal intermediates.

G. Claudon, N. Le Bris, H. Bernard, H. Handel

Eur. J. Org. Chem., 2004, 24, 5027-5030.

- Magnetic measurements, UV-Vis spectroscopy, and XAS of dinuclear nickel(II) complexes of bistetraazamacrocycles.

M. SOIBINET, I. DECHAMP-OLIVIER, E. GUILLON, J.-P. BARBIER, M. APLINCOURT, F. CHUBURU, M. LE BACCON, H. HANDEL.

Polyhedron, 2005, 24, 143-150.

- Mono and binuclear Cu(II) and Zn(II) complexes with bis-macrocycles containing two amino-alkyl pendant arms of different length.

C. Anda, A. Bencini, E. Berni, F. Chuburu, A. Danesi, C. Giorgi, H. Handel, M. Le Baccon, P. Paoletti, R. Tripier, V. Turcry, B. Valtancoli.

Eur. J. Inorg. Chem., 2005, 2044-2053.

- Spectroscopy and Redox Behaviour of Dicopper(II) and Dinickel(II) Complexesof bis(cyclen) and bis(cyclam)ligands

S. E. El GHATCHTOULI, C; CADIOU, I. DECHAMP-OLIVIER, F. CHUBURU, M. APLINCOURT, V. TURCRY, M. LE BACCON, H. HANDEL.

Eur. J. Inorg. Chem., 2005, 2658-2668.

- Cyclen based bis-macrocyclicligands as phosphates receptors.A potentiometric and NMR study. S. Develay, R. Tripier, M. Le Baccon, V. Patinec, G. Serratrice, H. Handel, Dalton Trans. 2005, 3016-3024.

- Synthesis of three dissymmetrical pentaamines via bisaminals of linear tetraamines.

G. CLAUDON, H. BERNARD, N. LE BRIS, H. HANDEL

J. Chem. Res., 2006, 000

- Nickel(II) complexes of cyclen and cyclam pyridine : topological reorganisations induced by electron transfer.

S. EL GHACHTOULI, C. CADIOU, I. DECHAMPS-OLIVIER, F. CHUBURU, M. APLINCOURT, V. PATINEC, M. LE BACCON, H. HANDEL, T. ROISNEL.

New Journal of Chemistry, 2006, 1, XXX

- Unexpected aggregation in aqueous solution of neutral, xylene-cored dinuclear GdIII chelates.

V. TURCRY, R. TRIPIER, M. LE BACCON, F. CHUBURU, H. HANDEL, J. COSTA, E. BALOGH, L. HELM, E. TÓTH, A. E. MERBACH.

Chem. Eur. J., 2006, 12, 6841-6851.

- New side-bridged bismacrocycles and cross-bridged macrotricycles. Syntheses and Cu(II) complexation study.

N. BERNIER, M. ALLALI, R. TRIPIER, F. CONAN, V. PATINEC, S. DÉVELAY, M. LE BACCON, H. HANDEL

New Journal of Chemistry, 2006, 1, 435-441

- Host-guest interaction between cyclen based macrotricyclic ligands and phosphate anions. A potentiometric investigation. S. Develay, R. Tripier, M. Le Baccon, V. Patinec, G. Serratrice, H. Handel, Dalton Trans. 2006, 3418-3426.

- Cyclohexanedione bisaminals as intermediates for cyclen, homocyclen and cyclam synthesis.

A. Prokhorov, N. Le Bris, H. Bernard, G. Claudon, H. Handel.

Synth. Commun., 2006, 36, XXX.

2007

- Complexation of the triphosphate anion: tuning the structure of cyclen based macrotricycles with 1,2-dimethylbenzene and 2,6-dimethylpyridine linkers. A potentiometric and NMR study. S. Develay, R. Tripier, N. Bernier, M. Le Baccon, V. Patinec, G. Serratrice, H. Handel, Dalton Trans. 2007, 1038-1046.

- A potentiometric and NMR investigation of triphosphate recognition by linear and bismacrocyclic octaamines possessing a 1,4-xylenyl linker. N. Le Bris, H. Bernard, R. Tripier, H. Handel, Inorg. Chim. Acta, 3026-3032.

- Proton-sponge behaviour of new pendant armed cross-bridged bis-cyclens. Synthesis, NMR, X-ray and potentiometric investigations. N. Bernier, R. Tripier, V. Patinec, M. Le Baccon, H. Handel. Comptes Rendus de Chimie, 832-838.

- Propionate derivatives of DOTA and DTPA : influence on the dissociation and formation kinetics of lanthanide(III) complexes. E. Balogh,R. Tripier, P. Fouskova, F. Reviriego,H. Handel, E. Tóth, Dalton Trans. 2007, 3572-3581.

THESIS (1989-2005)

Stéphanie Develay 2005	Synthèse de dimères de tétraazacycloalcanes. Etude de complexation des phosphates.
Géraldine Claudon 2004	Synthèse de tétraazamacrocycles et de tétramines linéaires modifiées via leurs intermédiaires bis-aminals
Véronique Turcry 2004	Les poly-tétraazamacrocycles. Synthèse via des intermédiaires bis-aminals - Complexation des ions de métaux de transition et de lanthanides
Marine Antoine 2001	Application des bis-aminals à la synthèse de tétramines linéaires et cycliques
Gwenaëlle Hervé 1999	Nouvelles synthèses de tétraazamacrocycles via les bisaminals de tétramines linéaires
Annaïg Roignan 1997	Azasilatranes macrocycliques
Nicolas Oget 1996	Tris-aminophosphoranes : synthèse et réactivité en série poly-azamacrocycles
Isabelle Gardinier 1996	Synthèse de bis-macrocycles dissymétriques
S. Ogor 1995	C-Fonctionnalisation de tétraazamacrocycles
V. Salou 1995	Tétraazamacrocycles greffés : synthèse et applications
Valérie Panetta 1993	Les Triflamides, intermédiaires de synthèse de polyazamacrocycles
Hélène Benard 1992	Synthèse des tétraazamacrocycles mono N-fonctionnalisés, triprotection temporaire par un atome de Bore
A. Filali 1991	Phosphorotriamides de tétraazamacrocycles intermédiaires de synthèse dans la réaction de mono N-fonctionnalisation
Hélène Chaumeil 1989	Mono N-fonctionnalisation de tétraazamacrocycles. Applications à la synthèse de nouvelles résines chélatantes
L. Percelay 1986	Application de tétraazamacrocycles greffés ou lipophiles à l'extraction et au dosage du cuivre, du zinc et du cadmium en eau de mer
V. Louvet 1985	Synthèse et propriétés complexantes de tétraazamacrocycles greffés sur polymère
E. Suet 1984	Synthèse et propriétés complexantes d'une série de tétraazamacrocycles
F. Muller 1982	Synthèse de tétraazamacrocycles lipophiles et application à l'extraction d'ions métalliques

LINKS

http://www.univ-brest.fr/Recherche/Laboratoire/UMR6521/

http://www.mairie-brest.fr/

http://www.cg29.fr/

http://www.region-bretagne.fr/CRB