Driving Triplet State Population in Benzothioxanthene Imide Dyes: Let's twist!

Darío Puchán Sánchez; Pierre Josse; Nathan Plassais; Geonwoo Park; Yeasin Khan; Yejoo Park; Mathilde Seinfeld; Antoine Guyard; Magali Allain; Frédéric Gohier; Lhoussain Khrouz; Dominik Lungerich; Hyun S. Ahn; Bright Walker; Cyrille Monnereau; Clément Cabanetos; Tangui Le Bahers

doi:10.1002/chem.202400191

Driving Triplet State Population in Benzothioxanthene Imide Dyes: Let's twist!

Darío Puchán Sánchez, Pierre Josse, Nathan Plassais, Geonwoo Park, Yeasin Khan, Yejoo Park, Mathilde Seinfeld, Antoine Guyard, Magali Allain, Frédéric Gohier, Lhoussain Khrouz, Dominik Lungerich, Hyun S. Ahn, Bright Walker, Cyrille Monnereau, Clément Cabanetos, Tangui Le Bahers

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Controlling the formation of photoexcited triplet states is critical for many (photo)chemical and physical applications. Here, we demonstrate that a permanent out-of-plane distortion of the benzothioxanthene imide (BTI) dye promotes intersystem crossing by increasing spin-orbit coupling. This manipulation was achieved through a subtle chemical modification, specifically the bay-area methylation. Consequently, this simple yet efficient approach expands the catalog of known molecular engineering strategies for synthesizing heavy atom-free, dual redox-active, yet still emissive and synthetically accessible photosensitizers.

Original language	English
Article number	e202400191
Journal	Chemistry - A European Journal
Volume	30
Issue number	27
DOIs	https://doi.org/10.1002/chem.202400191
Publication status	Published - 2024 May 14

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Organic Chemistry

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10.1002/chem.202400191

Cite this

Puchán Sánchez, D., Josse, P., Plassais, N., Park, G., Khan, Y., Park, Y., Seinfeld, M., Guyard, A., Allain, M., Gohier, F., Khrouz, L., Lungerich, D., Ahn, H. S., Walker, B., Monnereau, C., Cabanetos, C., & Le Bahers, T. (2024). Driving Triplet State Population in Benzothioxanthene Imide Dyes: Let's twist! Chemistry - A European Journal, 30(27), Article e202400191. https://doi.org/10.1002/chem.202400191

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abstract = "Controlling the formation of photoexcited triplet states is critical for many (photo)chemical and physical applications. Here, we demonstrate that a permanent out-of-plane distortion of the benzothioxanthene imide (BTI) dye promotes intersystem crossing by increasing spin-orbit coupling. This manipulation was achieved through a subtle chemical modification, specifically the bay-area methylation. Consequently, this simple yet efficient approach expands the catalog of known molecular engineering strategies for synthesizing heavy atom-free, dual redox-active, yet still emissive and synthetically accessible photosensitizers.",

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Puchán Sánchez, D, Josse, P, Plassais, N, Park, G, Khan, Y, Park, Y, Seinfeld, M, Guyard, A, Allain, M, Gohier, F, Khrouz, L, Lungerich, D, Ahn, HS, Walker, B, Monnereau, C, Cabanetos, C & Le Bahers, T 2024, 'Driving Triplet State Population in Benzothioxanthene Imide Dyes: Let's twist!', Chemistry - A European Journal, vol. 30, no. 27, e202400191. https://doi.org/10.1002/chem.202400191

TY - JOUR

T1 - Driving Triplet State Population in Benzothioxanthene Imide Dyes

T2 - Let's twist!

AU - Puchán Sánchez, Darío

AU - Josse, Pierre

AU - Plassais, Nathan

AU - Park, Geonwoo

AU - Khan, Yeasin

AU - Park, Yejoo

AU - Seinfeld, Mathilde

AU - Guyard, Antoine

AU - Allain, Magali

AU - Gohier, Frédéric

AU - Khrouz, Lhoussain

AU - Lungerich, Dominik

AU - Ahn, Hyun S.

AU - Walker, Bright

AU - Monnereau, Cyrille

AU - Cabanetos, Clément

AU - Le Bahers, Tangui

PY - 2024/5/14

Y1 - 2024/5/14

N2 - Controlling the formation of photoexcited triplet states is critical for many (photo)chemical and physical applications. Here, we demonstrate that a permanent out-of-plane distortion of the benzothioxanthene imide (BTI) dye promotes intersystem crossing by increasing spin-orbit coupling. This manipulation was achieved through a subtle chemical modification, specifically the bay-area methylation. Consequently, this simple yet efficient approach expands the catalog of known molecular engineering strategies for synthesizing heavy atom-free, dual redox-active, yet still emissive and synthetically accessible photosensitizers.

AB - Controlling the formation of photoexcited triplet states is critical for many (photo)chemical and physical applications. Here, we demonstrate that a permanent out-of-plane distortion of the benzothioxanthene imide (BTI) dye promotes intersystem crossing by increasing spin-orbit coupling. This manipulation was achieved through a subtle chemical modification, specifically the bay-area methylation. Consequently, this simple yet efficient approach expands the catalog of known molecular engineering strategies for synthesizing heavy atom-free, dual redox-active, yet still emissive and synthetically accessible photosensitizers.

KW - Dye chemistry

KW - benzothioxanthene imide

KW - intersystem crossing

KW - spin-orbit coupling

KW - structure-property relationships

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Driving Triplet State Population in Benzothioxanthene Imide Dyes: Let's twist!

Abstract

Bibliographical note

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