Asymmetric topology architecture improves polarity sensitivity of nitrogen and boron containing donor–acceptor luminogens: theoretical prediction and experimental validation

Abstract

Polarity-sensitive responsiveness is a crucial property for fluorescent probes, yet developing probes with high spectral sensitivity to polarity remains challenging. In this work, we systematically designed a series of donor–acceptor (D–A) type luminogens NNB and their derivatives with symmetric and asymmetric structures by fine-tuning the proportion of nitrogen-containing D moieties and boron-containing A moieties to elucidate the structure–property relationships governing their spectral responsiveness to solvent polarity. Our findings revealed a clear trend in polarity sensitivity of these dyes: symmetric dyes < asymmetric D–D–A dyes < asymmetric D–A–A dyes. The polarity responsive trend of these dyes was rigorously verified through combined theoretical and experimental approaches across various solvent conditions and polarity-tunable polymer-doped thin films. Importantly, our calculations revealed that for these dyes the conformational planarization and solute–solvent interactions synergistically induce the polarity-dependent fluorescence redshift. Crucially, we established a robust quantitative descriptor (ΔΔESSI-es), which represents the difference in solute–solvent interaction energies in different solvent environments. And ΔΔESSI-es shows strong correlation (R2 = 0.98) with the corresponding emission wavelength shifts (Δλem). This work not only offers fundamental insights for designing D–A type high-performance polarity-sensitive fluorescent probes with nitrogen-containing donors and boron-containing acceptors, but also delivers a practical descriptor for assessing spectral sensitivity to environmental polarity.

Graphical abstract: Asymmetric topology architecture improves polarity sensitivity of nitrogen and boron containing donor–acceptor luminogens: theoretical prediction and experimental validation

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2025
Accepted
24 Aug 2025
First published
27 Aug 2025

J. Mater. Chem. A, 2025, Advance Article

Asymmetric topology architecture improves polarity sensitivity of nitrogen and boron containing donor–acceptor luminogens: theoretical prediction and experimental validation

Y. Zeng, J. Zhao, F. Zhao, J. Duan, Z. Tan, J. Zhang, P. Chen and X. Zheng, J. Mater. Chem. A, 2025, Advance Article , DOI: 10.1039/D5TA03872C

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