Wydział Chemii

Rafał Frydrych

Kabali Senthilkumar

Katarzyna Ślusarek

Mateusz Waliczek

Wojciech Bury

Piotr J. Chmielewski

Joanna Cybińska

Marcin Stępień

2025

Organic Chemistry Frontiers

12

437-447

10.1039/d4qo01993h

Naukowa

Angielski

Artykuł

Two viologen-like macrocyclic receptors, [1]²⁺ and [2]²⁺, merging a bent oligophenylene loop with a (para-xylylene)bispyridinium moiety were designed and synthesized. Both dications were derived from the same precursor: the more strained cycloparaphenylene analogue [1]²⁺ was obtained using a reductive aromatization, whereas the less curved, meta-phenylene-containing [2]²⁺ was generated using a double eliminative rearrangement. [1]²⁺ is active as a receptor toward pyrene-1,3,6,8-tetrasulfonate, displaying a 2 : 1 binding interaction, with K₁₁ = 7.4(3) × 10³ M⁻¹. In the solid state, [1][TFA]₂ shows differential sorption of C₆ hydrocarbons and shows reversible sorption of water. [1]²⁺ displays yellow emission in solution (λ^em_max = 544 nm in DMF), which is considerably red shifted in the solid state (λ^em_max = 644 nm for dry samples). Both [1]²⁺ and [2]²⁺ undergo electrochemical reduction, yielding transient viologen-like radical cations and diradicals.

http://dx.doi.org/10.1039/D4QO01993H

https://www.rsc.org/