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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 &gt;650 nm, epsilon approximate to 2 x 10(6) m(-1) cm (-1)).

Název v anglickém jazyce

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

Popis výsledku anglicky

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 &gt;650 nm, epsilon approximate to 2 x 10(6) m(-1) cm (-1)).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GP14-02165P" target="_blank" >GP14-02165P: Červeně emitující fluorescenční senzory odvozené od struktury azaftalocyaninů: Studie aza-crownů jako rozpoznávací části</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

—

Svazek periodika

23

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

1795-1804

Kód UT WoS článku

000395754800012

EID výsledku v databázi Scopus

2-s2.0-85007207079