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

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Author(s):
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Antoneli, Rafael G. ; Moraes, Thaisa B. F. ; Junqueira, Helena C. ; Sihn, Luca M. ; Toma, Henrique E. ; Pedras, Bruno ; Ferreira, Luis F. V. ; Frath, Denis ; Bucher, Christophe ; Steed, Jonathan W. ; Demets, Gregoire J. -F. ; Triboni, Eduardo R.
Total Authors: 12
Document type: Journal article
Source: JOURNAL OF MATERIALS CHEMISTRY C; v. 12, n. 11, p. 9-pg., 2024-02-23.
Abstract

Naphthalenediimide amphiphiles (NDI-as) with quaternary ammonium groups (DC4, DaP, and DaO) display unprecedented UV light-induced aggregation in solutions of water, acetonitrile and THF. Light-induced aggregation brings significant spectral modification by which unusual absorption band distribution is assigned to H-type aggregates. Such aggregation can be reversibly broken by heating and reassembled by photoirradiation. The irradiation/heating cycles that provoke assembly/disassembly process can be confirmed by 1H-NMR spectroscopy. The possibility of a chemically promoted aggregation by or radical anion either anion-pi interaction may be ruled out by UV-Vis, EPR and electrochemistry measurements. These photoinduced aggregates can sensitize dissolved O2 to produce singlet oxygen, a surprising observation when it comes to sensitization efficiency for dyes as aggregation usually decreases sensitization yield. Laser-induced luminescence measurements corroborate the existence of monomeric and aggregate forms, as well as confirm triplet states as phosphorescence was detected, being particularly intense in concentrated THF solutions. Naphthalenediimide amphiphiles (NDI-as) with quaternary ammonium groups (DC4, DaP, and DaO) display unprecedented UV light-induced aggregation in solutions of water, acetonitrile and THF. (AU)

FAPESP's process: 21/01509-0 - Nanostructured gels and multicomponent supramolecular systems
Grantee:Eduardo Rezende Triboni
Support Opportunities: Regular Research Grants
FAPESP's process: 19/27157-3 - Photophysical and electrochemical study of organic semiconductor gels
Grantee:Thaisa Brandão Ferreira de Moraes
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 22/06346-5 - Multicomponent systems designed in bisureas and diimides
Grantee:Eduardo Rezende Triboni
Support Opportunities: Scholarships abroad - Research
FAPESP's process: 22/02711-0 - NDI-Niobium complexes by ultrasound and mechanical methods
Grantee:Rafael Gagliardi Antoneli
Support Opportunities: Scholarships in Brazil - Technical Training Program - Technical Training