Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions
Original language description
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 'knock-on' 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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)
Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dalton Transactions
ISSN
1477-9226
e-ISSN
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Volume of the periodical
48
Issue of the periodical within the volume
41
Country of publishing house
GB - UNITED KINGDOM
Number of pages
14
Pages from-to
15583-15596
UT code for WoS article
000496518600027
EID of the result in the Scopus database
2-s2.0-85073664888