pH-Sensitive subphthalocyanines and subazaphthalocyanines

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

pH-Sensitive subphthalocyanines and subazaphthalocyanines

Popis výsledku v původním jazyce

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) &lt; 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).

Název v anglickém jazyce

pH-Sensitive subphthalocyanines and subazaphthalocyanines

Popis výsledku anglicky

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) &lt; 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).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

<a href="/cs/project/EF16_019%2F0000841" target="_blank" >EF16_019/0000841: Zvýšení účinnosti a bezpečnosti léčiv a nutraceutik: moderní metody - nové výzvy</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Dalton Transactions

ISSN

1477-9226

e-ISSN

—

Svazek periodika

49

Číslo periodika v rámci svazku

32

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

11090-11098

Kód UT WoS článku

000561080600040

EID výsledku v databázi Scopus

2-s2.0-85089708467