@article{2c4dff58d98f42139d96d58e4c3bbccd,
title = "In Situ Synthesis of Phenoxazine Dyes in Water: Application for “Turn-On” Fluorogenic and Chromogenic Detection of Nitric Oxide**",
abstract = "The synthesis of phenoxazine dyes was revisited in order to access these fluorescent N,O-heterocycles under mild conditions. The combined sequential use of nitrosonium tetrafluoroborate (NOBF4) and triphenylphosphine enables the facile conversion of bis(3-dimethylaminophenyl) ether into the methyl analogue of popular laser dye oxazine 1. The ability of nitrosonium cation (NO+) to initiate the domino reaction resulting in π-conjugated phenoxazine molecules under neutral conditions, then led us to explore the feasibility of expanding it in aqueous media. Thus, we explored the use of reactive signaling molecule nitric oxide (NO) as a biological trigger of phenoxazine synthesis in water. The implementation of a robust analytical methodology based on fluorescence assays and HPLC-fluorescence/-MS analyses, have enabled us to demonstrate the viability of this novel fluorogenic reaction-based process to selectively yield an intense “OFF-ON” response in the near-infrared (NIR-I) spectral region. This study is an important step towards the popularization of the concept of “covalent assembly” in the fields of optical sensing, bioimaging and molecular theranostics.",
keywords = "covalent assembly, domino reactions, fluorescent probes, nitric oxide, phenoxazine dyes",
author = "S{\'e}bastien Jenni and K{\'e}vin Renault and Garance Dejouy and Sylvain Debieu and Myriam Laly and Anthony Romieu",
note = "Funding Information: This work is part of the project “MULTIMOD”, supported by the Conseil R{\'e}gional de Bourgogne Franche‐Comt{\'e} and the European Union through the PO FEDER‐FSE Bourgogne 2014/2020 programs. Financial supports from the French “Investissements d′Avenir” program, project ISITE BFC (contract ANR‐15‐IDEX‐0003), especially for the post‐doc fellowship of Dr. S{\'e}bastien Jenni, and Agence Nationale de la Recherche (ANR, AAPG 2018, PRCI, LuminoManufacOligo, ANR‐18‐CE07‐0045), especially for the post‐doc fellowship of Dr. K{\'e}vin Renault are also greatly acknowledged. GDR CNRS “Agents d′Imagerie Mol{\'e}culaire” (AIM) 2037 is also thanked for its interest in this research topic. The authors thank the “Plateforme d′Analyse Chimique et de Synth{\`e}se Mol{\'e}culaire de l′Universit{\'e} de Bourgogne” (PACSMUB, http://www.wpcm.fr ) for access to analytical and molecular spectroscopy instruments. COBRA lab (UMR CNRS 6014) and Iris Biotech company are warmly thanked for the generous gift of some chemical reagents used in this work. The authors also thank Dr. Jacques Pliquett (Ph. D. student, 2015–2018, UBFC, ICMUB, P2DA & OCS teams) for the synthesis of aza‐BODIPY dye used as a standard for determination of fluorescence quantum yields, and Prof. Ewen Bodio (University of Burgundy, ICMUB, UMR CNRS 6302, OCS team) for access to SAFAS Flx‐Xenius XC spectrofluorimeter. Funding Information: This work is part of the project “MULTIMOD”, supported by the Conseil R{\'e}gional de Bourgogne Franche-Comt{\'e} and the European Union through the PO FEDER-FSE Bourgogne 2014/2020 programs. Financial supports from the French “Investissements d′Avenir” program, project ISITE BFC (contract ANR-15-IDEX-0003), especially for the post-doc fellowship of Dr. S{\'e}bastien Jenni, and Agence Nationale de la Recherche (ANR, AAPG 2018, PRCI, LuminoManufacOligo, ANR-18-CE07-0045), especially for the post-doc fellowship of Dr. K{\'e}vin Renault are also greatly acknowledged. GDR CNRS “Agents d′Imagerie Mol{\'e}culaire” (AIM) 2037 is also thanked for its interest in this research topic. The authors thank the “Plateforme d′Analyse Chimique et de Synth{\`e}se Mol{\'e}culaire de l′Universit{\'e} de Bourgogne” (PACSMUB, http://www.wpcm.fr) for access to analytical and molecular spectroscopy instruments. COBRA lab (UMR CNRS 6014) and Iris Biotech company are warmly thanked for the generous gift of some chemical reagents used in this work. The authors also thank Dr. Jacques Pliquett (Ph. D. student, 2015–2018, UBFC, ICMUB, P2DA & OCS teams) for the synthesis of aza-BODIPY dye used as a standard for determination of fluorescence quantum yields, and Prof. Ewen Bodio (University of Burgundy, ICMUB, UMR CNRS 6302, OCS team) for access to SAFAS Flx-Xenius XC spectrofluorimeter. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",
year = "2022",
month = may,
doi = "10.1002/cptc.202100268",
language = "English",
volume = "6",
journal = "ChemPhotoChem",
issn = "2367-0932",
publisher = "Wiley-VCH",
number = "5",
}