FeCl3oxidation of the racemate of C2symmetric, inherently chiral, sexithiophene monomer 1 (2,2â²-bis(2,2â²-bithiophene-5-yl)-3,3â²-bithianaphthene) affords a mixture of cyclic oligomers, from the prevailing dimer to traces of the pentamer. The oligomers are constituted by mixtures of stereoisomers which are two for dimer 2, four for trimer 3 and six for tetramer 4. Cyclooligomers 2 and 3 could be separated by chromatography, while 4 was synthesized by ring closure of open chain dimer 2a, prepared in turn by controlled coupling of the anion of racemic 1. The optical properties of open-chain stereoisomer 2a and tetramer 4 have been compared with those of 2 and 3 respectively. The macrocyclic oligomers have been tested as donor materials in bulk heterojunction solar cell prototypes both as a crude mixture resulting from oxidation of 1 and as a single oligomer. Theoretical calculations support the photophysical properties of these new materials.
A family of solution-processable macrocyclic and open-chain oligothiophenes with atropoisomeric scaffolds : structural and electronic features for potential energy applications / E. Quartapelle Procopio, T. Benincori, G. Appoloni, P.R. Mussini, S. Arnaboldi, C. Carbonera, R. Cirilli, A. Cominetti, L. Longo, R. Martinazzo, M. Panigati, R. Pò. - In: NEW JOURNAL OF CHEMISTRY. - ISSN 1144-0546. - 41:18(2017), pp. 10009-10019.
|Titolo:||A family of solution-processable macrocyclic and open-chain oligothiophenes with atropoisomeric scaffolds : structural and electronic features for potential energy applications|
|Parole Chiave:||catalysis; chemistry (all); materials chemistry; 2506; metals and alloys|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
Settore CHIM/02 - Chimica Fisica
Settore CHIM/01 - Chimica Analitica
|Progetto:||Laboratorio multifunzionale e centro di formazione per la caratterizzazione e la sperimentazione preapplicativa di smart materials|
|Data di pubblicazione:||2017|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1039/c7nj01501a|
|Appare nelle tipologie:||01 - Articolo su periodico|