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Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F23%3A00578236" target="_blank" >RIV/61388963:_____/23:00578236 - isvavai.cz</a>

  • Alternative codes found

    RIV/00216224:14310/23:00132619 RIV/70883521:28110/23:63569878

  • Result on the web

    <a href="https://doi.org/10.1021/acs.joc.3c01556" target="_blank" >https://doi.org/10.1021/acs.joc.3c01556</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.joc.3c01556" target="_blank" >10.1021/acs.joc.3c01556</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril

  • Original language description

    Novel binding motifs suitable for the construction of multitopic guest-based molecular devices (e.g., switches, sensors, data storage, and catalysts) are needed in supramolecular chemistry. No rigid, aliphatic binding motif that allows for axial disubstitution has been described for cucurbit[6]uril (CB6) so far. We prepared three model guests combining spiro[3.3]heptane and bicyclo[1.1.1]pentane centerpieces with imidazolium and ammonium termini. We described their binding properties toward CB6/7 and α-/β-CD using NMR, titration calorimetry, mass spectrometry, and single-crystal X-ray diffraction. We found that a bisimidazolio spiro[3.3]heptane guest forms inclusion complexes with CB6, CB7, and β-CD with respective association constants of 4.0 × 104, 1.2 × 1012, and 1.4 × 102. Due to less hindering terminal groups, the diammonio analogue forms more stable complexes with CB6 (K = 1.4 × 106) and CB7 (K = 3.8 × 1012). The bisimidazolio bicyclo[1.1.1]pentane guest forms a highly stable complex only with CB7 with a K value of 1.1 × 1011. The high selectivity of the new binding motifs implies promising potential in the construction of multitopic supramolecular components.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2023

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Journal of Organic Chemistry

  • ISSN

    0022-3263

  • e-ISSN

    1520-6904

  • Volume of the periodical

    88

  • Issue of the periodical within the volume

    22

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    11

  • Pages from-to

    15615-15625

  • UT code for WoS article

    001092725700001

  • EID of the result in the Scopus database

    2-s2.0-85177807025