New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’ (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’ (Articolo in rivista) (literal)

Anno

• 2006-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1021/jo061446m (literal)

Alternative label

• G. Delogu; D. Fabbri; M. A. Dettori; M. Sallé; F. Le Derf; M-J. Blesa; Magali A. (2006)
  New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’
  in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• G. Delogu; D. Fabbri; M. A. Dettori; M. Sallé; F. Le Derf; M-J. Blesa; Magali A. (literal)

Pagina inizio

• 9096 (literal)

Pagina fine

• 9103 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

• http://pubs.acs.org/doi/pdf/10.1021/jo061446m (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 71 (literal)

Rivista

• Journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 8 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 24 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#descrizioneSinteticaDelProdotto

• A series of biphenyl-TTF derivatives bearing a binding site has been synthesized. Synergic steric influence of TTF substituents and crown-ether chain bonded to the biphenyl scaffold has been observed in conformationally flexible biphenyls by NMR experiments. This highlights how substituents at the meta-meta’ and ortho-ortho’ positions of the biphenyl are crucial in the tuning of dihedral angle and therefore in the preparation of TTF-biphenyl assemblies with electrochemical recognition behaviour. Our study confirms that it is possible to reach TTF-atropoisiomeric assemblies, starting from tropos biphenyls5j,m instead of conformationally stable biphenyls (atropos) or binaphthyls. In fact electrochemical behaviour of 3-6 appears to be strongly dependent on the conformational flexibility of the molecular assembly. In particular, the Pb+2 binding ability of one member of the series, compound 4, could be electrochemically (CV) addressed through conformational modifications relayed by the biphenyl scaffold. Such architectures constitute a suitable model to study long-distance conformational effects monitored electrochemically. Extension of this work to design new responsive receptors is under investigation. (literal)

Note

• Scopu (literal)
• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Istituto CNR di Chimica Biomolecolare, traversa La Crucca, 3, I-07040 Sassari, Italy, and Laboratoire Chimie, Ingenierie Moleculaire et Materiaux d'Angers (CIMMA), UMR CNRS 6200, Universite´ d'Angers, UFR Sciences, 2 Bd Lavoisier, F-49045 ANGERS Cedex, France (literal)

Titolo

• New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’ (literal)

Abstract

• Abstract : The synthesis of a family of biphenyl-tetrathiafulvalene derivatives incorporating a binding site has been carried out in good to moderate yields through functionalization of the biphenyl scaffold. X-ray structure of one derivative (compound 3) of the series is provided and shows a dihedral angle of 74° around the central Ar-Ar bond of the biphenyl unit in a cissin conformation. 1H-NMR and cyclic-voltammetry studies demonstrate the critical importance of the nature of the substitution on the conformational rigidity and on the electrochemical behaviour of the resulting biphenyl-TTF assemblies. This feature is underlined by an original electrochemical recognition process upon binding of Pb2+, correlated to conformational changes occurring upon metal cation complexation. (literal)

Editore

• ACS, American chemical society (Editore)

Prodotto di

• Sintesi, caratterizzazione e studio di composti chirali e chirali non racemi di interesse biologico mediante molecole ad alta simmetria (PM.P01.011.002) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• GIOVANNA MARIA DELOGU (Persona)
• DAVIDE GAETANO FABBRI (Unità di personale interno)
• MARIA ANTONIETTA DETTORI (Unità di personale interno)

Insieme di parole chiave

• Keywords of "New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• MARIA ANTONIETTA DETTORI (Unità di personale interno)
• DAVIDE GAETANO FABBRI (Unità di personale interno)
• GIOVANNA MARIA DELOGU (Persona)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Sintesi, caratterizzazione e studio di composti chirali e chirali non racemi di interesse biologico mediante molecole ad alta simmetria (PM.P01.011.002) (Modulo)

Editore di

• ACS, American chemical society (Editore)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Journal of organic chemistry (Rivista)

Insieme di parole chiave di

• Keywords of "New Electroactive C2 symmetry assemblies based on the biphenyl scaffold and tetrathiafulvalene (TTF) units’" (Insieme di parole chiave)