Phenol-Substituted Tetrapyrazinoporphyrazines: pH-Dependent Fluorescence in Basic Media

Kód výsledku v IS VaVaI

RIV/00216208:11160/15:10312720 - isvavai.cz

Výsledek na webu

http://onlinelibrary.wiley.com/doi/10.1002/chem.201502533/full

DOI - Digital Object Identifier

10.1002/chem.201502533

Jazyk výsledku

angličtina

Název v původním jazyce

Phenol-Substituted Tetrapyrazinoporphyrazines: pH-Dependent Fluorescence in Basic Media

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Phenol-Substituted Tetrapyrazinoporphyrazines: pH-Dependent Fluorescence in Basic Media

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

GP14-02165P: Červeně emitující fluorescenční senzory odvozené od struktury azaftalocyaninů: Studie aza-crownů jako rozpoznávací části

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

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

21

Číslo periodika v rámci svazku

41

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

14382-14392

Kód UT WoS článku

000363331600021

EID výsledku v databázi Scopus

2-s2.0-84942296368