Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F19%3A10405354" target="_blank" >RIV/00216208:11320/19:10405354 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=4YGbSRDkZB" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=4YGbSRDkZB</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c9dt02365h" target="_blank" >10.1039/c9dt02365h</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions

Popis výsledku v původním jazyce

Interactions of anionic guests with a tritopic peripherally functionalized conjugated calix[4]pyrrole host (1) prepared using a regioselective synthetic method is reported. The regioselectivity of synthesis relies on selective N-alkylation of the calix[4]pyrrole caused by peripheral substitution of one pyrrole group with subsequent N-alkylation at the opposing pyrrole group termed by us &apos;knock-on&apos; regioselectivity. The resulting host molecule exhibits anion interactions with common chloride and nitrate anions enhanced by an order of magnitude over the parent conjugated calix[4]pyrrole. Combined analysis of H-1 NMR and UV-vis spectroscopic titration data enabled an evaluation of binding strengths of anions with the host K-A in a binding model where the salt dissociation process is also incorporated in the form of its dissociation constant K-d. Anions could be classified as two types based on their interactions with 1: Type A anions (chloride, nitrate, perchlorate, hydrogensulphate) associate as 1:1 complexes through hydrogen bonding while interactions involving Type B anions (acetate, fluoride, dihydrogenphosphate) are complicated by host deprotonation and/or countercation association. Hosts based on rim-functionalized calix[4]pyrroles such as 1 represent a promising new family of chromophores for estimation of biologically relevant anions or other species.

Název v anglickém jazyce

Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions

Popis výsledku anglicky

Interactions of anionic guests with a tritopic peripherally functionalized conjugated calix[4]pyrrole host (1) prepared using a regioselective synthetic method is reported. The regioselectivity of synthesis relies on selective N-alkylation of the calix[4]pyrrole caused by peripheral substitution of one pyrrole group with subsequent N-alkylation at the opposing pyrrole group termed by us &apos;knock-on&apos; regioselectivity. The resulting host molecule exhibits anion interactions with common chloride and nitrate anions enhanced by an order of magnitude over the parent conjugated calix[4]pyrrole. Combined analysis of H-1 NMR and UV-vis spectroscopic titration data enabled an evaluation of binding strengths of anions with the host K-A in a binding model where the salt dissociation process is also incorporated in the form of its dissociation constant K-d. Anions could be classified as two types based on their interactions with 1: Type A anions (chloride, nitrate, perchlorate, hydrogensulphate) associate as 1:1 complexes through hydrogen bonding while interactions involving Type B anions (acetate, fluoride, dihydrogenphosphate) are complicated by host deprotonation and/or countercation association. Hosts based on rim-functionalized calix[4]pyrroles such as 1 represent a promising new family of chromophores for estimation of biologically relevant anions or other species.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>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

Dalton Transactions

ISSN

1477-9226

e-ISSN

—

Svazek periodika

48

Číslo periodika v rámci svazku

41

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

14

Strana od-do

15583-15596

Kód UT WoS článku

000496518600027

EID výsledku v databázi Scopus

2-s2.0-85073664888