Issue 7, 2020

Linking triptycene to silole: a fruitful association

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

Supplementary files

Article information

Article type
Research Article
Submitted
17 feb 2020
Accepted
01 mai 2020
First published
06 mai 2020

Mater. Chem. Front., 2020,4, 2006-2017

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, 4, 2006 DOI: 10.1039/D0QM00087F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements