Tetra(pyrazino[2,3-b] pyrazino) porphyrazines: Synthesis, absorption, photophysical and electrochemical properties of strongly electron-deficient macrocycles

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10364455" target="_blank" >RIV/00216208:11160/17:10364455 - isvavai.cz</a>

Výsledek na webu

<a href="http://www.worldscientific.com/doi/abs/10.1142/S1088424617500146" target="_blank" >http://www.worldscientific.com/doi/abs/10.1142/S1088424617500146</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1142/S1088424617500146" target="_blank" >10.1142/S1088424617500146</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Tetra(pyrazino[2,3-b] pyrazino) porphyrazines: Synthesis, absorption, photophysical and electrochemical properties of strongly electron-deficient macrocycles

Popis výsledku v původním jazyce

Highly electron deficient 6,7-disubstituted (tert-butylsufanyl, 2,6-diisopropylphenoxy, diethylamino, 2-pyridyl, 2-thienyl, 2-furyl) pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles were prepared and attempted in cyclotetramerization to corresponding tetra(pyrazino[2,3-b] pyrazino) porphyrazines (TPyzPyzPzs). Only the template reaction in pyridine with zinc acetate and only for the compounds substituted with tert-butylsulfanyl or 2,6-diisopropylphenoxy substituents resulted in efficient cyclotetramerization. Absorption spectra of these zinc TPyzPyzPzs indicated considerable blue shift of the main absorption Q-band (lambda(max) = 693 nm and 669 nm in pyridine for tert-butylsulfanyl or 2,6-diisopropylphenoxy derivatives) when compared to other aza-analogs of naphthalocyanines. Photophysical parameters (Phi(F) similar to 0.25, Phi(Delta) similar to 0.65) seemed to be unaffected by change of the macrocycle core and only slightly by different peripheral substituents in agreement with heavy-atom effect. Electrochemical data revealed strong electron-deficient character of hetaryl disubstituted pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles. The first reduction potentials of tert-butylsulfanyl or 2,6-diisopropylphenoxy substituted zinc TPyzPyzPzs were even more cathodically shifted when compared to their corresponding pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles. TPyzPyzPzs represent an example of the strongest electron-deficient core among the phthalocyanines, naphthalocyanines and their aza-analogs.

Název v anglickém jazyce

Tetra(pyrazino[2,3-b] pyrazino) porphyrazines: Synthesis, absorption, photophysical and electrochemical properties of strongly electron-deficient macrocycles

Popis výsledku anglicky

Highly electron deficient 6,7-disubstituted (tert-butylsufanyl, 2,6-diisopropylphenoxy, diethylamino, 2-pyridyl, 2-thienyl, 2-furyl) pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles were prepared and attempted in cyclotetramerization to corresponding tetra(pyrazino[2,3-b] pyrazino) porphyrazines (TPyzPyzPzs). Only the template reaction in pyridine with zinc acetate and only for the compounds substituted with tert-butylsulfanyl or 2,6-diisopropylphenoxy substituents resulted in efficient cyclotetramerization. Absorption spectra of these zinc TPyzPyzPzs indicated considerable blue shift of the main absorption Q-band (lambda(max) = 693 nm and 669 nm in pyridine for tert-butylsulfanyl or 2,6-diisopropylphenoxy derivatives) when compared to other aza-analogs of naphthalocyanines. Photophysical parameters (Phi(F) similar to 0.25, Phi(Delta) similar to 0.65) seemed to be unaffected by change of the macrocycle core and only slightly by different peripheral substituents in agreement with heavy-atom effect. Electrochemical data revealed strong electron-deficient character of hetaryl disubstituted pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles. The first reduction potentials of tert-butylsulfanyl or 2,6-diisopropylphenoxy substituted zinc TPyzPyzPzs were even more cathodically shifted when compared to their corresponding pyrazino[2,3-b] pyrazino-2,3-dicarbonitriles. TPyzPyzPzs represent an example of the strongest electron-deficient core among the phthalocyanines, naphthalocyanines and their aza-analogs.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

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

2017

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

—

Svazek periodika

21

Číslo periodika v rámci svazku

4-6

Stát vydavatele periodika

FR - Francouzská republika

Počet stran výsledku

9

Strana od-do

302-310

Kód UT WoS článku

000406378900008

EID výsledku v databázi Scopus

2-s2.0-85015620304