1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

Clotilde Philippe; Anh Thy Bui; Sabrinah Batsongo-Boulingui; Ziemowit Pokladek; Katarzyna Matczyszyn; Olivier Mongin; Loïc Lemiègre; Frédéric Paul; Trevor A. Hamlin; Yann Trolez

doi:10.1021/acs.orglett.1c00136

1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

Clotilde Philippe, Anh Thy Bui, Sabrinah Batsongo-Boulingui, Ziemowit Pokladek, Katarzyna Matczyszyn, Olivier Mongin, Loïc Lemiègre, Frédéric Paul, Trevor A. Hamlin, Yann Trolez^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2 + 2] or a [4 + 2] Diels-Alder process. DFT calculations unraveled the mechanism of the [2 + 2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR and far-red/near-IR photoluminescence in the solid state up to 1550 nm.

Original language	English
Pages (from-to)	2007-2012
Number of pages	6
Journal	Organic letters
Volume	23
Issue number	6
Early online date	26 Feb 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00136
Publication status	Published - 19 Mar 2021

Bibliographical note

Funding Information:
This study is part of the project ANR JCJC Fluotet 17-CE07-0038-01 from the Agence Nationale pour la Recherche. A.T.B. and C.P. thank the Région Bretagne for funding postdoctoral and doctoral grants, respectively. PHC Polonium 37629XG (2017-2018) is aknowledged for funding. The authors would like to acknowledge Dr. Olivier Maury (Laboratoire de Chimie at ENS de Lyon) for access to the Horiba Jobin-Yvon fluorometers. Dr. François Riobé (Laboratoire de Chimie at ENS de Lyon) is also thanked for assistance with the corresponding measurements and fruitful discussions. T.A.H. thanks The Netherlands Organization for Scientific Research (NWO) for support.

Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Funding

This study is part of the project ANR JCJC Fluotet 17-CE07-0038-01 from the Agence Nationale pour la Recherche. A.T.B. and C.P. thank the Région Bretagne for funding postdoctoral and doctoral grants, respectively. PHC Polonium 37629XG (2017-2018) is aknowledged for funding. The authors would like to acknowledge Dr. Olivier Maury (Laboratoire de Chimie at ENS de Lyon) for access to the Horiba Jobin-Yvon fluorometers. Dr. François Riobé (Laboratoire de Chimie at ENS de Lyon) is also thanked for assistance with the corresponding measurements and fruitful discussions. T.A.H. thanks The Netherlands Organization for Scientific Research (NWO) for support.

Funders	Funder number
Agence Nationale de la Recherche	17-CE07-0038-01
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Région Bretagne

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes",

abstract = "Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2 + 2] or a [4 + 2] Diels-Alder process. DFT calculations unraveled the mechanism of the [2 + 2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR and far-red/near-IR photoluminescence in the solid state up to 1550 nm. ",

author = "Clotilde Philippe and Bui, {Anh Thy} and Sabrinah Batsongo-Boulingui and Ziemowit Pokladek and Katarzyna Matczyszyn and Olivier Mongin and Lo{\"i}c Lemi{\`e}gre and Fr{\'e}d{\'e}ric Paul and Hamlin, {Trevor A.} and Yann Trolez",

note = "Funding Information: This study is part of the project ANR JCJC Fluotet 17-CE07-0038-01 from the Agence Nationale pour la Recherche. A.T.B. and C.P. thank the R{\'e}gion Bretagne for funding postdoctoral and doctoral grants, respectively. PHC Polonium 37629XG (2017-2018) is aknowledged for funding. The authors would like to acknowledge Dr. Olivier Maury (Laboratoire de Chimie at ENS de Lyon) for access to the Horiba Jobin-Yvon fluorometers. Dr. Fran{\c c}ois Riob{\'e} (Laboratoire de Chimie at ENS de Lyon) is also thanked for assistance with the corresponding measurements and fruitful discussions. T.A.H. thanks The Netherlands Organization for Scientific Research (NWO) for support. Publisher Copyright: {\textcopyright} 2021 American Chemical Society. All rights reserved. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

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AU - Bui, Anh Thy

AU - Batsongo-Boulingui, Sabrinah

AU - Pokladek, Ziemowit

AU - Matczyszyn, Katarzyna

AU - Mongin, Olivier

AU - Lemiègre, Loïc

AU - Paul, Frédéric

AU - Hamlin, Trevor A.

AU - Trolez, Yann

N1 - Funding Information: This study is part of the project ANR JCJC Fluotet 17-CE07-0038-01 from the Agence Nationale pour la Recherche. A.T.B. and C.P. thank the Région Bretagne for funding postdoctoral and doctoral grants, respectively. PHC Polonium 37629XG (2017-2018) is aknowledged for funding. The authors would like to acknowledge Dr. Olivier Maury (Laboratoire de Chimie at ENS de Lyon) for access to the Horiba Jobin-Yvon fluorometers. Dr. François Riobé (Laboratoire de Chimie at ENS de Lyon) is also thanked for assistance with the corresponding measurements and fruitful discussions. T.A.H. thanks The Netherlands Organization for Scientific Research (NWO) for support. Publisher Copyright: © 2021 American Chemical Society. All rights reserved. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/3/19

Y1 - 2021/3/19

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1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

Abstract

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