pH-Sensitive subphthalocyanines and subazaphthalocyanines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F20%3A10417833" target="_blank" >RIV/00216208:11160/20:10417833 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=Thy_VNOTWx" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=Thy_VNOTWx</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d0dt01703e" target="_blank" >10.1039/d0dt01703e</a>
Alternative languages
Result language
angličtina
Original language name
pH-Sensitive subphthalocyanines and subazaphthalocyanines
Original language description
Although subphthalocyanines (SubPcs) possess advantageous fluorescence properties and serve as an amazing tool to attach a recognition sensor moiety to the axial position, a limited number of switchable SubPcs have been described so far. Isosteric aza-replacement is known to improve sensing properties in closely related phthalocyanine families; however, pyrazino[2,3-b,g,l]subporphyrazines (SubPyzPzs) have not yet been investigated for use in sensing applications. Therefore, this project focuses on the synthesis and sensing abilities of pH-sensitive SubPcs and SubPyzPzs on the principle of photoinduced electron transfer (PET). 4-Dimethylaminophenoxy (for acidic pH) or 4-hydroxyphenoxy (for basic pH) groups were employed as pH-sensitive axial ligands. Electrochemical studies revealed improvements in the electron-accepting properties of SubPyzPzs (E-red -0.56 V vs. SCE) in comparison to those of SubPcs (E-red -1.0 V vs. SCE). Hydroxy groups on the axial phenoxy ligands of SybPyzPzs and SubPcs have been found to act as donors for PET. The sensing properties under basic conditions could not be studied, since all the SubPcs and SubPyzPzs decomposed under basic conditions, SubPyzPzs were more susceptible to this process. On the other hand, compounds with 4-dimethylaminophenoxy groups as axial ligands showed great potential for sensing applications. These compounds were nonfluorescent (Phi(F) < 0.01) in acetone due to efficient PET, while their fluorescence steeply increased by two orders of magnitude upon the addition of trifluoroacetic acid, reaching a Phi(F) value of up to 0.17 (lambda(em) range of 563-590 nm). These compounds maintained their sensing properties in aqueous medium after incorporation into microemulsions. The most basic derivative showed pK(A) = 2.95 with Phi(F) = 0.10 in the ON state (fluorescence enhancement factor = 46, lambda(em) = 577 nm).
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
30104 - Pharmacology and pharmacy
Result continuities
Project
<a href="/en/project/EF16_019%2F0000841" target="_blank" >EF16_019/0000841: Efficiency and safety improvement of current drugs and nutraceuticals: advanced methods - new challenges</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dalton Transactions
ISSN
1477-9226
e-ISSN
—
Volume of the periodical
49
Issue of the periodical within the volume
32
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
11090-11098
UT code for WoS article
000561080600040
EID of the result in the Scopus database
2-s2.0-85089708467