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A family of solution-processable macrocyclic and open-chain oligothiophenes with atropoisomeric scaffolds: structural and electronic features for potential energy applications

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Abstract

FeCl3 oxidation of the racemate of C2 symmetric, inherently chiral, sexithiophene monomer 1 (2,2′-bis(2,2′-bithiophene-5-yl)-3,3′-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.

Graphical abstract: A family of solution-processable macrocyclic and open-chain oligothiophenes with atropoisomeric scaffolds: structural and electronic features for potential energy applications

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Publication details

The article was received on 04 May 2017, accepted on 25 Jul 2017 and first published on 26 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01501A
Citation: New J. Chem., 2017, Advance Article
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    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 and R. Pò, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01501A

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