Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

Yuichi Hirai; Anna Wrona-Piotrowicz; Janusz Zakrzewski; Magdalena Ciechańska; Takahito Ohmura; Takashi Takeda; Takayuki Nakanishi; Rémi Métivier; Clémence Allain

doi:10.1039/D3TC03968D

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Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides†

Yuichi Hirai,

*^a Anna Wrona-Piotrowicz,

^b Janusz Zakrzewski,

^b Magdalena Ciechańska,

^b Takahito Ohmura,^d Takashi Takeda,

^a Takayuki Nakanishi,

^a Rémi Métivier

*^c and Clémence Allain

*^c

Author affiliations

* Corresponding authors

^a National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Japan
E-mail: hirai.yuichi@nims.go.jp

^b Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland

^c Université Paris-Saclay, ENS Paris-Saclay, CNRS, PPSM, 4 Avenue des Sciences, Gif-sur-Yvette, France
E-mail: remi.metivier@ens-paris-saclay.fr, clemence.allain@ens-paris-saclay.fr

^d National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Japan

Abstract

A family of (alkylsilyl)pyrene-1-carboxamides exhibits similar mechanofluorochromic responses upon grinding. However, their spontaneous fluorescence recovery processes are distinct despite their similarity in chemical structures and crystal packings. Fluorescence spectroscopy, crystallography, and nanomechanical tests revealed that the chromic direction is dominated by the packing motif, while the fluorescence recovery is driven by the intermolecular interactions and the reversibility of deformation.

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DOI: https://doi.org/10.1039/D3TC03968D
Article type: Paper
Submitted: 31 Oct 2023
Accepted: 19 Dec 2023
First published: 19 Jan 2024
This article is Open Access

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J. Mater. Chem. C, 2024,12, 1952-1957

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Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

Y. Hirai, A. Wrona-Piotrowicz, J. Zakrzewski, M. Ciechańska, T. Ohmura, T. Takeda, T. Nakanishi, R. Métivier and C. Allain, J. Mater. Chem. C, 2024, 12, 1952 DOI: 10.1039/D3TC03968D

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Journal of Materials Chemistry C

Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides†

Abstract

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Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

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