Enhancing Photoinduced Electron Transfer Efficiency of Fluorescent pH-​Probes with Halogenated Phenols

Daniel Aigner, Stefan Freunberger, Martin Wilkening, Robert Saf, Sergey Borisov*, Ingo Klimant

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Photoinduced electron transfer (PET), which causes pH-dependent quenching of fluorescent dyes, is more effectively introduced by phenolic groups than by amino groups which have been much more commonly used so far. That is demonstrated by fluorescence measurements involving several classes of fluorophores. Electrochemical measurements show that PET in several amino-modified dyes is thermodynamically favorable, even though it was not experimentally found, underlining the importance of kinetic aspects to the process. Consequently, the attachment of phenolic groups allows for fast and simple preparation of a wide selection of fluorescent pH-probes with tailor-made spectral properties, sensitive ranges, and individual advantages, so that a large number of applications can be realized. Fluorophores carrying phenolic groups may also be used for sensing analytes other than pH or molecular switching and signaling.
Original languageEnglish
Pages (from-to)9293-9300
JournalAnalytical Chemistry
Issue number18
Publication statusPublished - 2014

Fields of Expertise

  • Advanced Materials Science

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