Radical‐Formation Management: Towards Aza‐Analogues of the Benzothioxanthene Imide

While benzothioxanthene imide (BTI) has shown promise in organic electronics and more recently in photodynamic therapy, its full potential remains yet undiscovered. In this context, this study repots the synthesis and characterization of aza derivatives in which the characteristic sulfur atom is rep...

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Published in:ChemistryEurope 2024-01, Vol.2 (1), p.6264-n/a
Main Authors: Sánchez, Darío Puchán, Josse, Pierre, Mutovska, Monika G., Siegler, Benjamin, Allain, Magali, Morice, Korentin, Blanchard, Philippe, Gohier, Frédéric, Le Bahers, Tangui, Monnereau, Cyrille, Zagranyarski, Yulian, Lungerich, Dominik, Cabanetos, Clément
Format: Article
Language:English
Subjects:
benzothioxanthene imide
Chemical Sciences
dye chemistry
Nitrogen
NMR
Nuclear magnetic resonance
organic chemistry
radical reactions
structure-property relationship
Thin films
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Summary:While benzothioxanthene imide (BTI) has shown promise in organic electronics and more recently in photodynamic therapy, its full potential remains yet undiscovered. In this context, this study repots the synthesis and characterization of aza derivatives in which the characteristic sulfur atom is replaced by an amino group. Adapted from the synthetic route of the BTI, a way was found to control the electronic structure of the radical intermediates, by means of a simple chemical modification. As a result, either the thermodynamically six‐membered or the kinetically favored five‐membered ring regioisomers can selectively be accessed. Photophysical rationalization of their structure‐property relationships confirmed the richness, versatility and tunability of this class of rylene imide‐based dyes. Through the preparation of aza analogues of the benzothioxanthene imide, the reactivity of radical intermediates can be controlled, by mean of a simple chemical modification, to selectively afford either the thermodynamical or kinetic regioisomer. Rationalization of their structure‐property relationship highlights the rich, versatile and tunable photophysics of these dyes.
ISSN:2751-4765
2751-4765
DOI:10.1002/ceur.202300071