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Unprecedented light induced aggregation of cationic 1,4,5,8-naphthalenediimide amphiphiles

Antoneli, Rafael G.; Moraes, Thaisa B. F.; Junqueira, Helena C.; Sihn, Luca M.; Toma, Henrique E.; Pedras, Bruno; Ferreira, Luís F. V.; Frath, Denis; Bucher, Christophe; Steed, Jonathan W.; Demets, Gregóire J.-F.; Triboni, Eduardo R.

Unprecedented light induced aggregation of cationic 1,4,5,8-naphthalenediimide amphiphiles Thumbnail


Authors

Rafael G. Antoneli

Thaisa B. F. Moraes

Helena C. Junqueira

Luca M. Sihn

Henrique E. Toma

Bruno Pedras

Luís F. V. Ferreira

Denis Frath

Christophe Bucher

Gregóire J.-F. Demets

Eduardo R. Triboni



Abstract

Bola amphiphiles from naphthalenediimide (NDI-bas) with quaternary ammonium groups (DC4, DaP, and DaO) display association in solution, as well as, surprisingly, visible light promoted photochromism in concentrated solutions of water, acetonitrile and THF. The photochromism is correlated with an aggregation process that leads to a significant modification of the electronic transitions, resulting in an unusual absorption band distribution that points out to a type of H-aggregation in transverse. This assembly can be reversibly broken up by heating at 70 °C and adding bulk salt (NaBF4). By 1H-NMR spectroscopic analysis of the irradiation/heating cycle the assembly/disassembly process can be followed by the changes in peak width and intensity. These photoinduced aggregates can sensitize dissolved O2 to give singlet oxygen, a surprising observation when it comes to sensitization efficiency for dyes where aggregation usually decreases the sensitization yield. Laser-induced luminescence measurements corroborate the existence of triplet states as phosphorescence was detected, being particularly intense in concentrated THF solutions.

Citation

Antoneli, R. G., Moraes, T. B. F., Junqueira, H. C., Sihn, L. M., Toma, H. E., Pedras, B., Ferreira, L. F. V., Frath, D., Bucher, C., Steed, J. W., Demets, G. J.-F., & Triboni, E. R. (2024). Unprecedented light induced aggregation of cationic 1,4,5,8-naphthalenediimide amphiphiles. Journal of Materials Chemistry C Materials for optical and electronic devices, 12(11), 3888-3896. https://doi.org/10.1039/d3tc04178f

Journal Article Type Article
Acceptance Date Feb 21, 2024
Online Publication Date Feb 23, 2024
Publication Date Mar 21, 2024
Deposit Date Aug 8, 2024
Publicly Available Date Aug 8, 2024
Journal Journal of Materials Chemistry C
Print ISSN 2050-7526
Electronic ISSN 2050-7534
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 12
Issue 11
Pages 3888-3896
DOI https://doi.org/10.1039/d3tc04178f
Public URL https://durham-repository.worktribe.com/output/2744376

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