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Thiophene–pyrrole containing S,N-heteroheptacenes : synthesis, and optical and electrochemical characterisation

Title data

Wetzel, Christoph ; Vogt, Astrid ; Rudnick, Alexander ; Mena-Osteritz, Elena ; Köhler, Anna ; Bäuerle, Peter:
Thiophene–pyrrole containing S,N-heteroheptacenes : synthesis, and optical and electrochemical characterisation.
In: Organic Chemistry Frontiers. Vol. 4 (2017) Issue 8 . - pp. 1629-1635.
ISSN 2052-4129
DOI: https://doi.org/10.1039/c7qo00294g

Abstract in another language

A novel family of S,N-heteroheptacenes SN7a–d with a variable thiophene–pyrrole ratio and a 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 provides interesting structure–property relationships and gives valuable insights into the role of nitrogen atoms within the series of thiophene–pyrrole containing S,N-heteroheptacenes. Remarkable differences in 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 chemical oxidation were monitored and compared.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Chair Experimental Physics II - Optoelectronics of Soft Matter > Chair Experimental Physics II - Optoelectronics of Soft Matter - Univ.-Prof. Dr. Anna Köhler
Faculties
Faculties > Faculty of Mathematics, Physics und Computer Science
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Chair Experimental Physics II - Optoelectronics of Soft Matter
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 530 Physics
Date Deposited: 02 Jun 2017 05:38
Last Modified: 08 Feb 2022 13:26
URI: https://eref.uni-bayreuth.de/id/eprint/37359