Issue 29, 2023

Fluorination of naphthalimide–cyanostilbene derivatives to achieve dual-state emission luminogens with strong fluorescence in highly polar environments for bioimaging

Abstract

Organic luminogens (OLs) that emit strong fluorescence in both solution and the aggregated state, referred to as dual-state emission luminogens (DSEgens), are highly desirable because of their capability to achieve multiple functions within onefold materials. The fluorescence of OLs, including DSEgens, with intramolecular charge transfer characteristics, often decreases in solution as the solvent polarity increases, namely the positive solvatokinetic effect, resulting in inferior environmental stability. In this work, fluorination to naphthalimide (NI)–cyanostilbene (CS) derivatives was adopted to construct novel DSEgens (NICSF-X, X = B, P, M, and T, respectively). Steady-state and transient spectroscopies were utilized to study their photophysical properties, evidencing their DSE properties with fluorescence quantum yields (φ) ∼0.2–0.4 in solution and ∼0.5–0.9 as solids. In particular, strong fluorescence emission in highly polar solvents i.e., φ up to ∼0.4–0.5 in ethanol, was sustained for NICSF-Xs, possibly assisted by hydrogen bonding (H-bonding) formation. Theoretical calculations and single-crystal structure analysis rationalized the intense photoluminescence (PL) emission of NICSF-Xs in the solid state. In addition, NICSF-Xs showed two-photon absorption (2PA) behaviors in dual states and were successfully applied for HepG2 cell imaging with one-photon and 2PA excitation, with lipid droplet targeting. Our study suggests that functionalization of molecules by fluorination to introduce H-bonding is a promising strategy to enhance the environmental stability of fluorescence in solution and realize strong PL emission in highly polar solvents, which could be favorable for bioimaging.

Graphical abstract: Fluorination of naphthalimide–cyanostilbene derivatives to achieve dual-state emission luminogens with strong fluorescence in highly polar environments for bioimaging

Supplementary files

Article information

Article type
Paper
Submitted
06 Maijs 2023
Accepted
19 Jūn. 2023
First published
04 Jūl. 2023

J. Mater. Chem. B, 2023,11, 6859-6867

Fluorination of naphthalimide–cyanostilbene derivatives to achieve dual-state emission luminogens with strong fluorescence in highly polar environments for bioimaging

Q. Shi, Y. Ni, L. Yang, L. Kong, P. Gu, C. Wang, Q. Zhang, H. Zhou and J. Yang, J. Mater. Chem. B, 2023, 11, 6859 DOI: 10.1039/D3TB01034A

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