Design rules for oxoporphyrinogen ('OxP') as a versatile chromophore for efficient singlet oxygen generation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388980%3A_____%2F23%3A00571415" target="_blank" >RIV/61388980:_____/23:00571415 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1142/S1088424623500359" target="_blank" >https://doi.org/10.1142/S1088424623500359</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1142/S1088424623500359" target="_blank" >10.1142/S1088424623500359</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Design rules for oxoporphyrinogen ('OxP') as a versatile chromophore for efficient singlet oxygen generation

Popis výsledku v původním jazyce

Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore with strong broad absorption in the visible range. It is derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin by two-electron oxidation, and the OxP tetrapyrrole moiety exists in a saddle conformation. N-Alkylation of the OxP core nitrogen atoms can be used to functionalize the chromophore leading to a class of stable molecules with highly substituted peripheries. Substituted OxPs can act as singlet oxygen generators under light irradiation and the efficacy of this process is influenced by the multiplicity of N-substitution, and by the chemical identity of those substituents. Bromination of the macrocyclic beta-positions can also be used to control singlet oxygen generation by the relevant derivatives. We report the quantum yields of singlet oxygen generation for a series of differently substituted OxP derivatives whose metrics indicate that these compounds possess significant potential in the corresponding applications including photodynamic therapy, bacterial inactivation therapy, and organic transformations.

Název v anglickém jazyce

Design rules for oxoporphyrinogen ('OxP') as a versatile chromophore for efficient singlet oxygen generation

Popis výsledku anglicky

Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore with strong broad absorption in the visible range. It is derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin by two-electron oxidation, and the OxP tetrapyrrole moiety exists in a saddle conformation. N-Alkylation of the OxP core nitrogen atoms can be used to functionalize the chromophore leading to a class of stable molecules with highly substituted peripheries. Substituted OxPs can act as singlet oxygen generators under light irradiation and the efficacy of this process is influenced by the multiplicity of N-substitution, and by the chemical identity of those substituents. Bromination of the macrocyclic beta-positions can also be used to control singlet oxygen generation by the relevant derivatives. We report the quantum yields of singlet oxygen generation for a series of differently substituted OxP derivatives whose metrics indicate that these compounds possess significant potential in the corresponding applications including photodynamic therapy, bacterial inactivation therapy, and organic transformations.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

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

7

Stát vydavatele periodika

SG - Singapurská republika

Počet stran výsledku

11

Strana od-do

1108-1118

Kód UT WoS článku

000967458300001

EID výsledku v databázi Scopus

2-s2.0-85153933426