ArticleChemical science2015
A structural remedy toward bright dipolar fluorophores in aqueous media.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 162 citations in OpenAlex.
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- Rhodaelectro-Catalyzed peri-Selective Direct Alkenylations with Weak O-Coordination Enabled by the Hydrogen Evolution Reaction (HER).Angewandte Chemie (International ed. in English) · 2022Article
- Polarized, V-Shaped, and Conjoined Biscoumarins: From Lack of Dipole Moment Alignment to High Brightness.The Journal of organic chemistry · 2022Article
- A General Method to Develop Highly Environmentally Sensitive Fluorescent Probes and AIEgens.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2022Article
- NBD-based synthetic probes for sensing small molecules and proteins: design, sensing mechanisms and biological applications.Chemical Society reviews · 2021Review
- A Modular Fluorescent Probe for Viscosity and Polarity Sensing in DNA Hybrid Mesostructures.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2021Article
- Structurally symmetric near-infrared fluorophore IRDye78-protein complex enables multimodal cancer imaging.Theranostics · 2021Article
- A pyrene-based two-photon excitable fluorescent probe to visualize nuclei in live cells.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2020Article
- A Systematic Study of Coumarin-Tetrazine Light-Up Probes for Bioorthogonal Fluorescence Imaging.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
15 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The donor-acceptor (D-A) type dipolar fluorophores, an important class of luminescent dyes with two-photon absorption behaviour, generally emit strongly in organic solvents but poorly in aqueous media. To understand and enhance the poor emission behaviour of dipolar dyes in aqueous media, we undertake a rational approach that includes a systematic structure variation of the donor, amino substituent of acedan, an important two-photon dye. We identify several factors that influence the emission behaviour of the dipolar dyes in aqueous media through computational and photophysical studies on new acedan derivatives. As a result, we can make acedan dyes emit bright fluorescence under one- and two-photon excitation in aqueous media by suppressing the liable factors for poor emission: 1,3-allylic strain, rotational freedom, and hydrogen bonding with water. We also validate that these findings can be generally extended to other dipolar fluorophores, as demonstrated for naphthalimide, coumarin and (4-nitro-2,1,3-benzoxadiazol-7-yl)amine (NBD) dyes. The new acedan and naphthalimide dyes thus allow us to obtain much brighter two-photon fluorescent images in cells and tissues than in their conventional forms. As an application of these findings, a thiol probe is synthesized based on a new naphthalimide dye, which shows greatly enhanced fluorescence from the widely used
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Registered trials
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