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Linking triptycene to silole: a fruitful association

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Abstract

1,1′-Disubstituted-2,3,4,5-tetraphenylsiloles incorporating triptycene moieties Tp-DMTPS and Tp-MPTPS were prepared and characterized. Like other 2,3,4,5-tetraphenylsiloles, both compounds exhibit aggregation-induced emission (AIE) behavior. Unexpectedly, the solid state PL emission of Tp-DMTPS show dependence according to the degree of crystallinity of the powders. While precipitates display a blue-green emission, microcrystalline powders emit in the yellow-orange region. Moreover a rare reversible mechanohypsochromic phenomenom is observed: upon grinding, the emission of a micro-crystalline powder changes from yellow-orange to blue-green, the original emission being restored by annealing the sample. The mechanism of this blue-shift upon crystal grinding was investigated by X-ray diffraction, 13C CP-MAS NMR and DFT calculations. Under mechanical stress, strong intermolecular CH/π interactions are found to promote the less energetically stable population of conformers present in the crystals, leading to this blue-shift. Finally the influence of the triptycene moieties on the thermal and structural stability of Tp-DMTPS and Tp-MPTPS was studied. Compared with DMTPS and MPTPS parents, a general enhancement of the properties is noticed, especially when used as active layer in OLED fabrication. Our results suggest that the attachment of triptycene moieties to π-conjugated molecules is an interesting way to improve their thermal, structural and photophysical properties for sensing or optoelectronic applications.

Graphical abstract: Linking triptycene to silole: a fruitful association

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Supplementary files

Article information


Submitted
17 Feb 2020
Accepted
01 May 2020
First published
06 May 2020

Mater. Chem. Front., 2020, Advance Article
Article type
Research Article

Linking triptycene to silole: a fruitful association

K. Amro, A. K. Thakur, M. Rolland, A. Van Der Lee, V. Lemaur, R. Lazzaroni, J. Rault-Berthelot, C. Poriel, L. Hirsch, S. Clément and P. Gerbier, Mater. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QM00087F

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