Jump to main content
Jump to site search


Thiophene-Pyrrole Containing S,N-Heteroheptacenes: Synthesis, Optical, and Electrochemical Characterisation

Abstract

A novel family of S,N-heteroheptacenes SN7a-d with variable thiophene-pyrrole ratio and heteroring fusion sequence is presented. All SN7-derivatives can be synthesized in efficient multi-step synthetic routes with good overall yields. The crucial cyclization step to the stable and soluble fused systems is achieved by multiple Pd-catalyzed Buchwald-Hartwig aminations or C-S coupling reaction in high yields. The comparison of the optoelectronic properties provide interesting structure-property relationships and give valuable insights into the role of nitrogen atoms within the series of thiophene-pyrrole containing S,N-heteroheptacenes. Remarkable differences in the emission behaviour and noticeable correlations of the oxidation potentials of the S,N-heteroheptacenes offer helpful information for the construction of other heteroacenes. Additionally, UV-vis/NIR absorption spectra of the corresponding radical cations generated by che¬mical oxidation were monitored and compared.

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 16 Apr 2017, accepted on 11 May 2017 and first published on 15 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00294G
Citation: Org. Chem. Front., 2017, Accepted Manuscript
  •   Request permissions

    Thiophene-Pyrrole Containing S,N-Heteroheptacenes: Synthesis, Optical, and Electrochemical Characterisation

    P. Baeuerle, C. Wetzel, A. Vogt, A. Rudnick, E. Mena-Osteritz and A. Köhler, Org. Chem. Front., 2017, Accepted Manuscript , DOI: 10.1039/C7QO00294G

Search articles by author