Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and .beta.-substitution

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F19%3A00520750" target="_blank" >RIV/61389013:_____/19:00520750 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.worldscientific.com/doi/abs/10.1142/S1088424619501463" target="_blank" >https://www.worldscientific.com/doi/abs/10.1142/S1088424619501463</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1142/S1088424619501463" target="_blank" >10.1142/S1088424619501463</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and .beta.-substitution

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 derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin. It exhibits a wide range of chromogenic responses to solvents (solvatochromism), anions and acidic media (halochromism) making it potentially useful as an analytical reagent. The chromogenic responses of OxP can be modulated by varying its chemical structure, and this is reviewed here based on the introduction of substituents at central nitrogen atoms or pyrrolic β-positions. OxP and its N-alkylated derivates Bn2OxP and Bn4OxP have been used to estimate acidity in non-polar solvents. Bn2OxP can also be used to determine enantiomeric excesses of chiral substances. N-alkylation has also been used to introduce higher functional groups such as porphyrins to prepare self-assembling systems. β-Substitution has been used to introduce selectivity of anion interactions including towards basic anions (fluoride, cyanide) and polyoxoanions (nitrate, perchlorate, etc.). These aspects make OxP a highly adaptable tetrapyrrole molecule for sensing and other applications.

Název v anglickém jazyce

Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and .beta.-substitution

Popis výsledku anglicky

Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin. It exhibits a wide range of chromogenic responses to solvents (solvatochromism), anions and acidic media (halochromism) making it potentially useful as an analytical reagent. The chromogenic responses of OxP can be modulated by varying its chemical structure, and this is reviewed here based on the introduction of substituents at central nitrogen atoms or pyrrolic β-positions. OxP and its N-alkylated derivates Bn2OxP and Bn4OxP have been used to estimate acidity in non-polar solvents. Bn2OxP can also be used to determine enantiomeric excesses of chiral substances. N-alkylation has also been used to introduce higher functional groups such as porphyrins to prepare self-assembling systems. β-Substitution has been used to introduce selectivity of anion interactions including towards basic anions (fluoride, cyanide) and polyoxoanions (nitrate, perchlorate, etc.). These aspects make OxP a highly adaptable tetrapyrrole molecule for sensing and other applications.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10404 - Polymer science

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2019

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

23

Číslo periodika v rámci svazku

11/12

Stát vydavatele periodika

FR - Francouzská republika

Počet stran výsledku

11

Strana od-do

1184-1194

Kód UT WoS článku

000508130500003

EID výsledku v databázi Scopus

2-s2.0-85074602508