A macrocyclic receptor containing two viologen species connected by conjugated terphenyl groups
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43916903" target="_blank" >RIV/60461373:22310/18:43916903 - isvavai.cz</a>
Alternative codes found
RIV/61388955:_____/18:00499064
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2018/ob/c8ob00919h" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2018/ob/c8ob00919h</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c8ob00919h" target="_blank" >10.1039/c8ob00919h</a>
Alternative languages
Result language
angličtina
Original language name
A macrocyclic receptor containing two viologen species connected by conjugated terphenyl groups
Original language description
A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular N center dot center dot center dot N separation of ca. 7.4 angstrom. Thus, the internal cavity dimensions are suitable for the inclusion of pi-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E-1/2 = -0.65 and -0.97 V vs. Fc/Fc(+)). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a p-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (+/- 30 M-1) as calculated from H-1 NMR titration studies.
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
10402 - Inorganic and nuclear chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic and Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
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Volume of the periodical
16
Issue of the periodical within the volume
27
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
5006-5015
UT code for WoS article
000438393200012
EID of the result in the Scopus database
2-s2.0-85049890088