OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10361040" target="_blank" >RIV/00216208:11160/17:10361040 - isvavai.cz</a>
Result on the web
<a href="http://onlinelibrary.wiley.com/doi/10.1002/chem.201604978" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/chem.201604978</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201604978" target="_blank" >10.1002/chem.201604978</a>

Result language
angličtina
Original language name
OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window
Original language description
A unique combination of two independent mechanisms of fluorescence quenching, namely intramolecular charge transfer (ICT) from a peripheral donor and protonation of azomethine nitrogen atoms in zinc tetrapyrazinoporphyrazines (TPyzPz), provides a new possibility for sensing pH in a specific range. The pH selectivity was controlled by the different basicities of the donor for ICT (dimethylaminoaryl), which was connected to the macrocycle by pi-extended linkers of different lengths. ICT and protonation have been studied in detail by photophysical, spectral (UV/Vis and MCD spectra), and electrochemical measurements, and further supported by theoretical calculations (DFT, TDDFT). The pH-sensing properties of the TPyzPzs have been investigated in THF and in water after anchoring the TPyzPzs to liposomes. The salient pK(a) values were around 1.3 (azomethine nitrogen) and 2.29-4.76 (donor for ICT). The lead indicators (sensing over a pH range of 1.0-2.5) with fairly steep sensing profiles exhibited increases in fluorescence between the OFF/ON states of more than 20-fold and strong absorption in the red region (Q-band maximum >650 nm, epsilon approximate to 2 x 10(6) m(-1) cm (-1)).
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GP14-02165P" target="_blank" >GP14-02165P: Red-emitting Fluorescence Sensors Based on Azaphthalocynine Structure: Study of Aza-Crown Recognition Moiety</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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