http://www.cnr.it/ontology/cnr/individuo/prodotto/ID51252

Self-Organization, Optical, and Electrical Properties of alpha-Quinquethiophene-Dinucleotide Conjugates (Articolo in rivista)

Type

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

Label

Self-Organization, Optical, and Electrical Properties of alpha-Quinquethiophene-Dinucleotide Conjugates (Articolo in rivista) (literal)

Anno

2009-01-01T00:00:00+01:00 (literal)

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

10.1002/chem.200801684 (literal)

Alternative label

S. Alesi, G. Brancolini, I. Viola, M.L. Capobianco, A. Venturini, N. Camaioni, G. Gigli, M. Melucci, and G. Barbarella (2009)
Self-Organization, Optical, and Electrical Properties of alpha-Quinquethiophene-Dinucleotide Conjugates
in Chemistry - A European Journal; WILEY-V C H VERLAG GMBH,, D-69451 WEINHEIM, (Germania)
(literal)

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

S. Alesi, G. Brancolini, I. Viola, M.L. Capobianco, A. Venturini, N. Camaioni, G. Gigli, M. Melucci, and G. Barbarella (literal)

Pagina inizio

1876 (literal)

Pagina fine

1885 (literal)

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

15 (literal)

Rivista

Chemistry - A European Journal (Rivista)

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

8 (literal)

Note

ISI Web of Science (WOS) (literal)

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

Istituto CNR-ISOF Istituto CNR-NANO Università del Salento (literal)

Titolo

Self-Organization, Optical, and Electrical Properties of alpha-Quinquethiophene-Dinucleotide Conjugates (literal)

Abstract

The synthesis and properties of (5')TA(3')-t5 (8a) and (5')CG(3')-t5 (8b) conjugates, in which the self-complementary dinucleotides TA and CG are covalently bound to the central ring of alpha-quinquethiophene (t5), are described. According to molecular mechanics calculations, the preferred conformation of both 8 a and 8b is that with the dinucleotide folded over the planar t5 backbone, with the nucleobases facing t5 at stacking distance. The calculations show that the aggregation process of 8 a and 8b is driven by a mix of nucleobase-thiophene interactions, hydrogen bonding between nucleobases (non Watson-Crick (W&C) in TA, and W&C in CG), van der Waals, and electrostatic interactions. While 8b is scarcely soluble in any solvents, 8a is soluble in water, indicating that the aggregates of the former are more stable than those of the latter. Microfluidic-induced self-assembly studies of 8a showed the formation of lamellar, spherulitic, and dendritic supramolecular structures, depending on the concentration and solvent evaporation time. The self-assembled structures displayed micrometer dimensions in the. v plane of the substrate and nanometer dimensions in the z direction. Spatially resolved confocal microscopy and spectroscopy showed that the aggregates were characterized by intense fluorescence emission. Cast films of 8a from water solutions showed chirality transfer from the dinucleotide to t5. The hole mobility of the cast films of 8a was estimated using a two-electrode device under high vacuum and found to be up to two orders of magnitude greater than those previously measured for dinucleotide-quarterthiophene conjugates under the same experimental conditions. (literal)

Editore