Phenol-Substituted Tetrapyrazinoporphyrazines: pH-Dependent Fluorescence in Basic Media
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F15%3A10312720" target="_blank" >RIV/00216208:11160/15:10312720 - isvavai.cz</a>
Result on the web
<a href="http://onlinelibrary.wiley.com/doi/10.1002/chem.201502533/full" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/chem.201502533/full</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201502533" target="_blank" >10.1002/chem.201502533</a>
Alternative languages
Result language
angličtina
Original language name
Phenol-Substituted Tetrapyrazinoporphyrazines: pH-Dependent Fluorescence in Basic Media
Original language description
Tetrapyrazinoporphyrazines (TPyzPzs) bearing one, two, four or eight 3,5-di(tert-butyl)-4-hydroxyphenol moieties were synthesized as zinc(II) complexes and metal-free derivatives. The deprotonation of the phenol using tetrabutylammonium hydroxide inducedthe formation of a strong donor for intramolecular charge transfer that switched OFF the red fluorescence (lambda(F) ~ 660 nm) of the parent zinc TPyzPzs. The changes were fully reversible for TPyzPzs with one to four phenolic moieties, and an irreversible modification was observed for TPyzPzs substituted with eight phenols. The sensors were anchored to lipophilic particles in water, and a pK(a) approximately 12.5-12.7 was determined for the phenolic hydroxyl based on fluorescence changes in differentbuffers. In addition, a novel concept for fluorescence OFF-ON-OFF switching in metal-free TPyzPzs bearing phenolic moieties upon addition of specific amounts of base was demonstrated.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
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
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
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Volume of the periodical
21
Issue of the periodical within the volume
41
Country of publishing house
DE - GERMANY
Number of pages
11
Pages from-to
14382-14392
UT code for WoS article
000363331600021
EID of the result in the Scopus database
2-s2.0-84942296368