Structural Modulation of Chromic Response: Effects of Binding-Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F18%3A10385543" target="_blank" >RIV/00216208:11320/18:10385543 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1002/open.201800005" target="_blank" >https://doi.org/10.1002/open.201800005</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/open.201800005" target="_blank" >10.1002/open.201800005</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Structural Modulation of Chromic Response: Effects of Binding-Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

Popis výsledku v původním jazyce

Herein, we modulate the chromic response of a highly colored tetrapyrrole macrocycle, namely, tetrakis(3,5-di-tert-butyl-4-oxocyclohexadien-2,5-yl)porphyrinogen (OxP) by structural modification. N-Benzylation at the macrocyclic nitrogen atoms leads to stepwise elimination of the two calix[4]pyrrole-type binding sites of OxP and serial variation of the chromic properties of the products, double N-benzylated Bz(2)OxP and tetra N-benzylated Bz(4)OxP. The halochromic (response to acidity) and solvatochromic (response to solvent polarity) properties were studied by using UV/Vis spectroscopy and NMR spectroscopy in nonpolar organic solvents. Titration experiments were used to generate binding isotherms to elucidate their binding properties with difluoroacetic acid. Differences in the halochromic properties of the compounds allowed construction of a colorimetric scale of acidity in nonpolar solvents, as the compounds in the series OxP, Bz(2)OxP, and Bz(4)OxP are increasingly difficult to protonate but maintain their propensity to change color upon protonation. The concurrent effects of binding-site blocking and modulation of acidity sensitivity are important new aspects for the development of colorimetric indicators.

Název v anglickém jazyce

Structural Modulation of Chromic Response: Effects of Binding-Site Blocking in a Conjugated Calix[4]pyrrole Chromophore

Popis výsledku anglicky

Herein, we modulate the chromic response of a highly colored tetrapyrrole macrocycle, namely, tetrakis(3,5-di-tert-butyl-4-oxocyclohexadien-2,5-yl)porphyrinogen (OxP) by structural modification. N-Benzylation at the macrocyclic nitrogen atoms leads to stepwise elimination of the two calix[4]pyrrole-type binding sites of OxP and serial variation of the chromic properties of the products, double N-benzylated Bz(2)OxP and tetra N-benzylated Bz(4)OxP. The halochromic (response to acidity) and solvatochromic (response to solvent polarity) properties were studied by using UV/Vis spectroscopy and NMR spectroscopy in nonpolar organic solvents. Titration experiments were used to generate binding isotherms to elucidate their binding properties with difluoroacetic acid. Differences in the halochromic properties of the compounds allowed construction of a colorimetric scale of acidity in nonpolar solvents, as the compounds in the series OxP, Bz(2)OxP, and Bz(4)OxP are increasingly difficult to protonate but maintain their propensity to change color upon protonation. The concurrent effects of binding-site blocking and modulation of acidity sensitivity are important new aspects for the development of colorimetric indicators.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

ChemistryOpen [online]

ISSN

2191-1363

e-ISSN

—

Svazek periodika

7

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

13

Strana od-do

323-335

Kód UT WoS článku

000433494000003

EID výsledku v databázi Scopus

2-s2.0-85047659058