Issue 15, 2022

Facile construction of AIE-active pyridinyl-diphenylacrylonitrile derivatives with optical properties finely modulated by D–A regulation

Abstract

A series of simply-structured adducts of pyridine and diphenylacrylonitrile, i.e. PyDPACNs, featuring aggregation-induced emission (AIE) characteristics have been designed according to the principle of restriction of intramolecular motion (RIM), and facilely constructed via simple Knoevenagel condensation and Suzuki–Miyaura cross-coupling. The optical properties of these AIEgens could be finely modulated by the regulation of the electron-donating (D)–electron-accepting (A) effect, with the substituent on the terminal of the PyDPACN framework ranging from a strong D to strong A group. Interestingly, the role of the pyridinyl group could be flipped from an electron acceptor to an electron donor. Emission maxima of these PyDPACNs vary from 439 to 635 nm, covering nearly the whole visible light region. Amongst them, PyDPACNs with the strongest D (i.e. PyDPACN-N) or A group (i.e. PyDPACN-TCF) show the most significant intramolecular charge transfer (ICT) effect. PyDPACN-TCF possesses a high singlet-oxygen generation ability under white-light irradiation as well as moderate cytotoxicity in dark. The AIE mechanism, i.e. the RIM principle, was clarified through X-ray single crystal diffraction analysis. Density functional theory (DFT) calculations uncovered the electron-cloud distribution of PyDPACN derivatives in the ground and excited states, which not only reveals the role reversal of the pyridinyl moiety and the mutual conversion of D and A groups, but also provides an explanation for their distinct photophysical behaviours. The present work could provide both a new avenue for spectral modulation and effective molecular platforms for the development of advanced functional materials.

Graphical abstract: Facile construction of AIE-active pyridinyl-diphenylacrylonitrile derivatives with optical properties finely modulated by D–A regulation

Supplementary files

Article information

Article type
Research Article
Submitted
21 May 2022
Accepted
13 Haz 2022
First published
13 Haz 2022

Mater. Chem. Front., 2022,6, 2103-2113

Facile construction of AIE-active pyridinyl-diphenylacrylonitrile derivatives with optical properties finely modulated by D–A regulation

Y. Wang, Y. Zhong, X. Zhang, D. Qu, D. Mei and J. Mei, Mater. Chem. Front., 2022, 6, 2103 DOI: 10.1039/D2QM00477A

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