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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

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

Publication year

2017

Confidentiality

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

Name of the periodical

Journal of Porphyrins and Phthalocyanines

ISSN

1088-4246

e-ISSN

—

Volume of the periodical

21

Issue of the periodical within the volume

4-6

Country of publishing house

FR - FRANCE

Number of pages

9

Pages from-to

302-310

UT code for WoS article

000406378900008

EID of the result in the Scopus database

2-s2.0-85015620304