Synthesis and Photophysical, Electrochemical and Theoretical Study of Thiazole-Annelated Phthalocyanines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F15%3A10317262" target="_blank" >RIV/00216208:11160/15:10317262 - isvavai.cz</a>

Výsledek na webu

<a href="http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500785/full" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500785/full</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201500785" target="_blank" >10.1002/ejoc.201500785</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Photophysical, Electrochemical and Theoretical Study of Thiazole-Annelated Phthalocyanines

Popis výsledku v původním jazyce

Phthalocyanines with annelated thiazole rings were synthesised by cyclotetramerisation of benzothiazoledicarbonitriles. Three types of these dicarbonitriles with ortho-configuration were prepared from disubstituted anilines and their cyclisation led to all possible patterns of annelation in the phthalocyanine skeleton. Further substitution at the periphery of the macrocycle by methyl or tert-butyl substituents was realised to improve the solubility or to allow further derivatisation of target molecules.The characteristic UV/Vis spectral Q-bands were shifted to higher wavelengths (712-729 nm) because of the higher delocalisation, and fluorescence quantum yields increased compared with isoelectronic naphthalocyanines. Aggregation properties of the studied phthalocyanines were dependent on the type of isomer. The effects of the annelation pattern on the redox potentials were also investigated. Experimental data are compared with theoretical values obtained by DFT calculations.

Název v anglickém jazyce

Synthesis and Photophysical, Electrochemical and Theoretical Study of Thiazole-Annelated Phthalocyanines

Popis výsledku anglicky

Phthalocyanines with annelated thiazole rings were synthesised by cyclotetramerisation of benzothiazoledicarbonitriles. Three types of these dicarbonitriles with ortho-configuration were prepared from disubstituted anilines and their cyclisation led to all possible patterns of annelation in the phthalocyanine skeleton. Further substitution at the periphery of the macrocycle by methyl or tert-butyl substituents was realised to improve the solubility or to allow further derivatisation of target molecules.The characteristic UV/Vis spectral Q-bands were shifted to higher wavelengths (712-729 nm) because of the higher delocalisation, and fluorescence quantum yields increased compared with isoelectronic naphthalocyanines. Aggregation properties of the studied phthalocyanines were dependent on the type of isomer. The effects of the annelation pattern on the redox potentials were also investigated. Experimental data are compared with theoretical values obtained by DFT calculations.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

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

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

2015

Číslo periodika v rámci svazku

32

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

16

Strana od-do

7053-7068

Kód UT WoS článku

000364532000011

EID výsledku v databázi Scopus

2-s2.0-84946209272