Université de Neuchâtel

Supramolecular Fullerene Materials: Dendritic Liquid-Crystalline Fulleropyrrolidines

Campidelli, Stéphane ; Lenoble, Julie ; Barberá, Joaquín ; Paolucci, Francesco ; Marcaccio, Massimo ; Paolucci, Demis ; Deschenaux, Robert

In: Macromolecules, 2005, vol. 38, no. 19, p. 7915–7925

[60]Fullerene-containing liquid-crystalline dendrimers were synthesized from the first to the fourth generation by applying the 1,3-dipolar cycloaddition reaction from a mesomorphic dendritic-type aldehyde derivative, sarcosine (N-methylglycine) or glycine and C60. The cyanobiphenyl unit was used as a liquid-crystalline promoter. With the exception of the first-generation...

Université de Neuchâtel

Liquid-Crystalline Bisadducts of [60]Fullerene

Campidelli, Stéphane ; Vázquez, Ester ; Milic, Dragana ; Lenoble, Julie ; Atienza Castellanos, Carmen ; Sarova, Ginka ; Guldi, Dirk M. ; Deschenaux, Robert ; Prato, Maurizio

In: The Journal of Organic Chemistry (JOC), 2006, vol. 71, no. 20, p. 7603–7610

A second-generation cyanobiphenyl-based dendrimer was used as a liquid-crystalline promoter to synthesize mesomorphic bisadducts of [60]fullerene. Liquid-crystalline trans-2, trans-3, and equatorial bisadducts were obtained by condensation of the liquid-crystalline promoter, which carries a carboxylic acid function, with the corresponding bisaminofullerene derivatives. A monoadduct...

Université de Neuchâtel

Liquid−Crystalline Janus-Type Fullerodendrimers Displaying Tunable Smectic−Columnar Mesomorphism

Lenoble, Julie ; Campidelli, Stéphane ; Maringa, Natacha ; Donnio, Bertrand ; Guillon, Daniel ; Yevlampieva, Natalia ; Deschenaux, Robert

In: Journal of the American Chemical Society (JACS), 2007, vol. 129, no. 32, p. 9941–9952

Janus-type liquid−crystalline fullerodendrimers were synthesized via the 1,3-dipolar cycloaddtition of two mesomorphic dendrons and C60. By assembling poly(aryl ester) dendrons functionalized with cyanobiphenyl groups, displaying lamellar mesomorphism, with poly(benzyl ether) dendrons carrying alkyl chains, which display columnar mesomorphism, we could tailor by design the...

Université de Neuchâtel

Liquid-Crystalline Fullerodendrimers which Display Columnar Phases

Lenoble, Julie ; Maringa, Natacha ; Campidelli, Stéphane ; Donnio, Bertrand ; Guillon, Daniel ; Deschenaux, Robert

In: Organic Letters, 2006, vol. 8, no. 9, p. 1851–1854

The title compounds were synthesized by applying the 1,3-dipolar cycloaddition reaction of aldehyde-based poly(benzyl ether) dendrimers and sarcosine (N-methylglycine) to [60]fullerene (C60). The dendritic building blocks used to functionalize C60 displayed cubic and hexagonal columnar phases. The fullerene derivatives showed rectangular columnar phases of c2mm...

Université de Neuchâtel

Liquid-Crystalline Fulleropyrrolidines, Preliminary Communication

Campidelli, Stéphane ; Deschenaux, Robert

In: Helvetica Chimica Acta, 2001, vol. 84, no. 3, p. 589-593

A fulleropyrrolidine showing a smectic A phase was synthesized by 1,3-dipolar cycloaddition of a liquid-crystalline aldehyde derivative and sarcosine to C60.

Université de Neuchâtel

Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene–peralkylated ferrocene dyad

Campidelli, Stéphane ; Séverac, Marjorie ; Scanu, David ; Deschenaux, Robert ; Vázquez, Ester ; Milic, Dragana ; Prato, Maurizio ; Carano, Maurizio ; Marcaccio, Massimo ; Paolucci, Francesco ; Rahman, G. M. Aminur ; Guldi, Dirk M.

In: Journal of Materials Chemistry, 2008, vol. 18, p. 1504-1509

Two fullerene–peralkylated ferrocene derivatives were synthesized: (1) a liquid-crystalline dyad (compound 1) was obtained by introduction of nonamethyl ferrocene into a liquid-crystalline fullerene derivative and (2) a reference compound (compound 2) was synthesized by attachment of nonamethyl ferrocene to a fulleropyrrolidine. The liquid-crystalline dyad displayed an enantiotropic smectic A...

Université de Neuchâtel

Encoding calamitic mesomorphism in thermotropic lanthanidomesogens

Terazzi, Emmanuel ; Bocquet, Bernard ; Campidelli, Stéphane ; Donnio, Bertrand ; Guillon, Daniel ; Deschenaux, Robert ; Piguet, Claude

In: Chemical Communications (ChemComm), 2006, vol. 27, p. 2922-2924

Peripheral cyanobiphenyl dendrimers impose a microphase organization compatible with smectic mesomorphism, in which the bulky nine-coordinate lanthanide core is located between the decoupled mesogenic sublayers made up of parallel cyanobiphenyl groups.

Université de Neuchâtel

A dendritic fullerene–porphyrin dyad

Campidelli, Stéphane ; Deschenaux, Robert ; Swartz, Angela ; Rahman, G. M. Aminur ; Guldi, Dirk M. ; Milic, Dragana ; Vázquez, Ester ; Prato, Maurizio

In: Photochemical & Photobiological Sciences, 2006, vol. 5, no. 12, p. 1137-1141

We describe the synthesis, characterization and photophysical properties of a fullerene derivative whose structure includes a Zn-porphyrin and a second generation liquid-crystalline (LC) dendrimer. The size of the fullerene and porphyrin units with respect to the size of the LC dendrimer prevents the formation of liquid-crystalline phases. However, this system gives interesting photoinduced...

Université de Neuchâtel

Dendritic liquid-crystalline fullerene–ferrocene dyads

Campidelli, Stéphane ; Pérez, Laura ; Rodríguez-López Julián ; Barberá, Joaquín ; Langa, Fernando ; Deschenaux, Robert

In: Tetrahedron, 2006, vol. 62, no. 9, p. 2115-2122

First- and second-generation ferrocene-based dendrimers, fullerene and a second-generation liquid-crystalline poly(arylester) dendrimer carrying four cyanobiphenyl units were assembled to elaborate polyfunctional materials displaying mesomorphic and electronic properties. The targeted compounds gave rise to enantiotropic smectic A phases and organized into bilayer structures within the smectic...

Université de Neuchâtel

An optically-active liquid-crystalline hexa-adduct of [60]fullerene which displays supramolecular helical organization

Campidelli, Stéphane ; Brandmüller, Torsten ; Hirsch, Andreas ; Saez, Isabel M. ; Goodby, John W. ; Deschenaux, Robert

In: Chemical Communications, 2006, vol. 41, p. 4282 - 4284

Polyaddition of mesogenic moieties to C60 were found to yield chiral supermolecular nanoparticles which exhibit iridescent helical chiral nematic phases.