Nitration of benzothioxanthene: Towards a new class of dyes with versatile photophysical properties

José María Andrés Castán, Laura Abad Galán, Shi Li, Clément Dalinot, Pablo Simón Marqués, Magali Allain, Chad Risko, Cyrille Monnereau, Olivier Maury, Philippe Blanchard, Clément Cabanetos

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

The selective mono-nitration of benzothioxanthane (BTXI) is demonstrated herein. This leap opens doors to a wide range of chemical reactions since the nitro compound was successfully reduced to a primary amine that was, in turn, converted into an azide. Beyond this chemical achievement, this new series of functionalized BTXI was fully characterized, including from a photophysical point of view, expanding the scope of this promising rylene to build a new electroactive π-conjugated platform for electronic organic purposes.

Original languageEnglish
Pages (from-to)900-905
Number of pages6
JournalNew Journal of Chemistry
Volume44
Issue number3
DOIs
StatePublished - 2020

Bibliographical note

Funding Information:
(Projet étoile montante SAMOA). Benjamin Siegler is thanked for his help with structure solving by NMR experiments. LAG thanks Agence Nationale de la Recherche (SADAM ANR-16-CE07-0015-02) for her grant. S. L. and C. R. acknowledge the Office of Naval Research Young Investigator Program (award no. N00014-18-1-2448) for their support in this project. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and the Center for Computational Sciences (CCS).

Funding Information:
The authors thank the MATRIX SFR of the University of Angers. J. M. A. C. and P. S. M. acknowledge the European Union’s Horizon 2020 research and innovation program under Marie Sklodowska Curie Grant agreement No. 722651 (SEPOMO). The Région Pays de la Loire is acknowledged for the grant of C. D.

Publisher Copyright:
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Materials Chemistry

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