ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Dual-state emission of anthracene and triphenylamine functionalized E-cyanostilbene derivative with mechanochromic property

Gaobin Zhang, Shuyi Yao, Mengjie Miao, Jianli Yan, Fangjie Chen, and Jiaxiang Yang

Henan Key Laboratory of Materials on Deep‑Earth Engineering, School of Materials Science and Engineering, Henan Polytechnic University, Jiaozuo, People’s Republic of China

E-mail: gbzhang@hpu.edu.cn

Received: 26 February 2025  Accepted: 19 May 2025

Abstract:

In this work, an anthracene and triphenylamine functionalized E-cyanostilbene derivative (EN-TPA) was designed, synthesized and characterized. EN-TPA possessed excellent dual-state emission (DSE) property, possessing highly efficient emission both in solution and solid state. Meanwhile, the EN-TPA displayed obviously solvatochromic effect due to the intermolecular charge transfer, as confirmed by the Lippert–Mataga equation and quantum chemistry theoretical calculations. In aggregation state, EN-TPA was bright emissive with the solid fluorescence quantum yield (Φ_f) of 52.2%. Notably, the solid fluorescence of EN-TPA showed a 20 nm red shift after grinding, accompanied by a 4-fold decrease in Φ_f, attributed to the transition of crystalline to amorphous phase under grinding. Leveraging the reversible mechanochromic, the storage paper device of EN-TPA was fabricated and exhibited a distinct fluorescence change from green to yellow upon mechanical stimulation. Single-crystal X-ray diffraction analysis revealed that the twisted molecular structure of EN-TPA inhibited the π-π stacking and induced the molecule to form loose packing arrangements to achieve bright solid emission and stimulus response property. This work provides a new perspective for designing high-performing DSE molecules.

Graphical abstract

Keywords: Fluorescent dyes; Molecular Electronics; Organic Molecules in Materials Science; Single-molecule Fluorescence; Supramolecular Chemistry; Supramolecular Polymers; Dual-state emission; Fluorescence; Mechanochromic; E-cyanostilbene

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-025-04143-z

Chemical Papers 79 (8) 5533–5541 (2025)