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Synlett 2018; 29(19): 2577-2581
DOI: 10.1055/s-0037-1610331
cluster
© Georg Thieme Verlag Stuttgart · New York

Scalable Synthesis of Naphthothiophene-based D-π-D Extended Oligomers through Cascade Direct Arylation Processes

Andrea Nitti
a   Department of Chemistry and INSTM Research Unit, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy
,
Peshawa Osw
a   Department of Chemistry and INSTM Research Unit, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy
b   Department of Chemistry, Salahaddin University, 44001 Erbil, Kurdistan, Iraq
,
Media N. Abdullah
b   Department of Chemistry, Salahaddin University, 44001 Erbil, Kurdistan, Iraq
,
Alessandro Galbiati
c   New Polyurethane Technologies s.r.l., Via Stazione 12, 27030 Villanova D’ardenghi, Pavia, Italy   Email: dario.pasini@unipv.it
,
Dario Pasini  *
a   Department of Chemistry and INSTM Research Unit, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy
› Author AffiliationsWe gratefully acknowledge the University of Pavia and Salahaddin University for support.
Further Information

Publication History

Received: 03 October 2018

Accepted after revision: 06 November 2018

Publication Date:
12 November 2018 (online)

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Published as part of the Cluster Synthesis of Materials§These authors contributed equally.

Abstract

The synthesis of two novel π-extended oligomers, incorporating naphtho[1,2-b]thiophene-4-carboxylate 2-octyldodecyl esters as end-capping moieties, and two different conjugated core fragments, has been achieved through a cascade sequence of sustainable organic reactions. Benzo[c][1,2,5]thiadiazole and 2-octyldodecyl benzo[1,2-b:6,5-b′]dithiophene-4-carboxylate have been used, respectively, as electron-poor and electro-rich π-conjugated cores. In the latter case, a sequence of nine aromatic rings in a fully conjugated structure is achieved with a high yielding, sustainable cascade approach. The optoelectronic properties of both oligomers are reported.

Key words

cascade organic reactions - π-conjugated oligomers - direct arylation - organic electronics - fused aromatic rings

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610331.
  • Supporting Information
 

  • References and Notes

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