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

doi:10.1039/c9nj05804d

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 journal › Article › peer-review

9 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 language	English
Pages (from-to)	900-905
Number of pages	6
Journal	New Journal of Chemistry
Volume	44
Issue number	3
DOIs	https://doi.org/10.1039/c9nj05804d
State	Published - 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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10.1039/c9nj05804d

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title = "Nitration of benzothioxanthene: Towards a new class of dyes with versatile photophysical properties",

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.",

author = "{Andr{\'e}s Cast{\'a}n}, {Jos{\'e} Mar{\'i}a} and {Abad Gal{\'a}n}, Laura and Shi Li and Cl{\'e}ment Dalinot and {Sim{\'o}n Marqu{\'e}s}, Pablo and Magali Allain and Chad Risko and Cyrille Monnereau and Olivier Maury and Philippe Blanchard and Cl{\'e}ment Cabanetos",

note = "Funding Information: (Projet {\'e}toile 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{\textquoteright}s Horizon 2020 research and innovation program under Marie Sklodowska Curie Grant agreement No. 722651 (SEPOMO). The R{\'e}gion Pays de la Loire is acknowledged for the grant of C. D. Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

year = "2020",

doi = "10.1039/c9nj05804d",

language = "English",

volume = "44",

pages = "900--905",

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T1 - Nitration of benzothioxanthene

T2 - Towards a new class of dyes with versatile photophysical properties

AU - Andrés Castán, José María

AU - Abad Galán, Laura

AU - Li, Shi

AU - Dalinot, Clément

AU - Simón Marqués, Pablo

AU - Allain, Magali

AU - Risko, Chad

AU - Monnereau, Cyrille

AU - Maury, Olivier

AU - Blanchard, Philippe

AU - Cabanetos, Clément

N1 - 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.

PY - 2020

Y1 - 2020

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

Abstract

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