para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F24%3A00138672" target="_blank" >RIV/00216224:14310/24:00138672 - isvavai.cz</a>

Alternative codes found

RIV/70883521:28110/24:63579338

Result on the web

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202400535" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202400535</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.202400535" target="_blank" >10.1002/chem.202400535</a>

Result language

angličtina

Original language name

para–Phenylenediamine Dimer as a Redox–Active Guest for Supramolecular Systems

Original language description

Redox–active components are highly valuable in the construction of molecular devices. We combined two p-phenylenediamines (p-PDA) with a biphenyl (BiPhe) unit to prepare a supramolecular guest 4 consisting of three binding sites for cucurbit[7/8]uril (CBn) and/or cyclodextrins (CD). Supramolecular properties of 4 were investigated using NMR, UV-vis, mass spectrometry and isothermal titration calorimetry. Our analysis revealed that 4 forms higher–order host–guest complexes, wherein a CD unit occupies the central BiPhe site, secured by two CBn units at the terminal p-PDA sites. Additionally, 1 : 1 complexes with α-CD and β-CD, a 1 : 2 complex with γ-CD and 2 : 1 complexes with CB7 and CB8 were identified. Through UV-vis and cyclic voltammetry, redox processes leading to the formation of a stable, deep blue dication diradical of 4 are elucidated. Furthermore, it is demonstrated that CB7 selectively protects oxidised 4 from reduction in the presence of a reducing agent. The supramolecular and redox properties of the structural motif represented by 4 render it an interesting candidate for the construction of supramolecular devices.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10400 - Chemical sciences

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2024

Confidentiality

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

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

1521-3765

Volume of the periodical

30

Issue of the periodical within the volume

25

Country of publishing house

DE - GERMANY

Number of pages

12

Pages from-to

1-12

UT code for WoS article

001188552000001

EID of the result in the Scopus database

2-s2.0-85188232192