We have reengineered a red-emitting dicyanomethylenedihydrofuran push-pull fluorophore so that it is dark until photoactivated with a short burst of low-intensity violet light. Photoactivation of the dark fluorogen leads to conversion of an azide to an amine, which shifts the absorption to long wavelengths. After photoactivation, the fluorophore is bright and photostable enough to be imaged on the single-molecule level in living cells. This proof-of-principle demonstration provides a new class of bright photoactivatable fluorophores, as are needed for super-resolution imaging schemes that require active control of single molecule emission.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2688641PMC
http://dx.doi.org/10.1021/ja802883kDOI Listing

Publication Analysis

Top Keywords

push-pull fluorophore
8
photoactivatable push-pull
4
fluorophore single-molecule
4
single-molecule imaging
4
imaging live
4
live cells
4
cells reengineered
4
reengineered red-emitting
4
red-emitting dicyanomethylenedihydrofuran
4
dicyanomethylenedihydrofuran push-pull
4

Similar Publications

Fluorescent sensing technology has advantages such as high sensitivity, good selectivity, and easy operation. It is widely used in the environment and biomedical field and receives increasing attention from people. It is easy to modify the structure of the benzothiazole fluorophores, and adding the push-pull electronic system can regulate the optical properties of benzodiapylene molecules.

View Article and Find Full Text PDF

A facile method for the synthesis of arylidene derivatives of pyrindane - ()-7-arylmethylene-2-chloro-6,7-dihydro-5-cyclopenta[]pyridine-3,4-dicarbonitriles - was developed. Tunable full-color emission was achieved for the synthesized push-pull molecules, solely by changing donor groups while keeping both the conjugated system and acceptor part of the molecule unchanged. This represents a rare approach for the design of such fluorophores.

View Article and Find Full Text PDF

Balancing Brightness and Photobasicity: Modulating Excited-State Proton Transfer Pathways in Push-Pull Fluorophores for Biological Two-Photon Imaging.

J Phys Chem A

November 2024

School of Chemistry and Biochemistry and Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332, United States.

Article Synopsis
  • Push-pull fluorophores with donor-π-acceptor structures are useful for two-photon microscopy, enhancing brightness through charge-delocalization in excited states.
  • The study focused on the fluorescent probe chromis-1, revealing that its pH-dependent emission is influenced by intramolecular proton transfer rather than direct deprotonation of water.
  • A modification of the pyridine nitrogen's position in the fluorophore significantly reduced its excited-state basicity, emphasizing the need for careful design in fluorescent probes to limit pH-induced variations in response.
View Article and Find Full Text PDF

Owing to the carcinogenicity and environmental risks as well as the wide industrial use of hydrazine, we report herein a colorimetric probe for its ratiometric detection in pure water. The developed probe possesses push-pull architecture with 2-(piperidyn-1-yl) thiophene as the donor, N,N'-dibutylbarbituric as the acceptor, and butadiene as the spacer. In contrast to weak solvatochromic behavior in organic solvents, the probe showed distinct optical photophysical properties in water resulting from the formation of nanoscopic aggregates.

View Article and Find Full Text PDF

Amino-Terephthalonitrile and Amino-Terephthalate-Based Single Benzene Fluorophores - Compact Color Tunable Molecular Dyes for Bioimaging and Bioanalysis.

Chem Asian J

December 2024

Department of Chemistry, BITS Pilani K.K. Birla Goa Campus, NH 17B, Bypass Road, Zuarinagar, Goa, 403726, India.

This review article discusses the emerging amino-terephthalonitrile (Am-TN) and amino terephthalate-based single benzene fluorophores (SBFs) for their highly emissive nature and potential for numerous technical applications. Am-TN-SBFs are a new class of SBFs having amine as the electron donating (EDG) and dinitrile as the electron withdrawing group (EWG). The beauty of these Am-TN-SBFs lies in excellent intramolecular charge transfer between the EDG and EWG.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!