Synthesis of peripherally substituted aza-analogues of Si(IV) phthalocyanines by complexation method

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F23%3A10471240" target="_blank" >RIV/00216208:11160/23:10471240 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=6GLB3MlwIJ" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=6GLB3MlwIJ</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1142/S108842462350013X" target="_blank" >10.1142/S108842462350013X</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of peripherally substituted aza-analogues of Si(IV) phthalocyanines by complexation method

Popis výsledku v původním jazyce

Despite many notes about advantageous properties of Si(IV) phthalocyanines, their aza-analogues from the group of tetrapyrazinoporphyrazines (TPyzPzs) are only rarely reported in the literature, especially for macrocycles carrying peripheral groups. Thus, a series of Si(IV) TPyzPzs having alkylamino, aryloxy, alkylsulfanyl or alkyl group at the periphery was prepared by complexation of Si(IV) into corresponding metal-free derivatives by their stirring at 30 degrees C with trichlorosilane, using tributylamine as a base, and dichloromethane as a solvent. Key factors affecting the feasibility of this method, such as well-chosen excess of trichlorosilane and solvent used, were described. The model compound of the series (i.e., aryloxy substituted dihydroxy Si(IV) TPyzPz) was then modified at axial positions using trihexylchlorosilane as a ligand. All target Si(IV) TPyzPzs showed strong absorption with Q-band maxima ranging 617-655 nm (extinction coefficients 82 000-341 000 L.mol(-1).cm(-1)) and efficient fluorescence emission with Phi(F) values ranging 0.32-0.44 with the exception of alkylamino substituted TPyzPz, whose excited states were efficiently quenched by intramolecular charge transfer. The possibility of axial modification, good spectral and fluorescence properties as well as the ability to quench the excited states upon introduction of alkylamine groups indicate the suitability of these derivatives for fluorescence sensing applications.

Název v anglickém jazyce

Synthesis of peripherally substituted aza-analogues of Si(IV) phthalocyanines by complexation method

Popis výsledku anglicky

Despite many notes about advantageous properties of Si(IV) phthalocyanines, their aza-analogues from the group of tetrapyrazinoporphyrazines (TPyzPzs) are only rarely reported in the literature, especially for macrocycles carrying peripheral groups. Thus, a series of Si(IV) TPyzPzs having alkylamino, aryloxy, alkylsulfanyl or alkyl group at the periphery was prepared by complexation of Si(IV) into corresponding metal-free derivatives by their stirring at 30 degrees C with trichlorosilane, using tributylamine as a base, and dichloromethane as a solvent. Key factors affecting the feasibility of this method, such as well-chosen excess of trichlorosilane and solvent used, were described. The model compound of the series (i.e., aryloxy substituted dihydroxy Si(IV) TPyzPz) was then modified at axial positions using trihexylchlorosilane as a ligand. All target Si(IV) TPyzPzs showed strong absorption with Q-band maxima ranging 617-655 nm (extinction coefficients 82 000-341 000 L.mol(-1).cm(-1)) and efficient fluorescence emission with Phi(F) values ranging 0.32-0.44 with the exception of alkylamino substituted TPyzPz, whose excited states were efficiently quenched by intramolecular charge transfer. The possibility of axial modification, good spectral and fluorescence properties as well as the ability to quench the excited states upon introduction of alkylamine groups indicate the suitability of these derivatives for fluorescence sensing applications.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Journal of Porphyrins and Phthalocyanines

ISSN

1088-4246

e-ISSN

1099-1409

Svazek periodika

27

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

FR - Francouzská republika

Počet stran výsledku

8

Strana od-do

444-451

Kód UT WoS článku

000941200800005

EID výsledku v databázi Scopus

2-s2.0-85149851218