Year: 2025
Type: article
Abstract: A transporter for a directional macrocycle transport, release, and recapture was constructed. This was achieved using a rotaxane featuring a dibenzo-24-crown-8 macrocycle, dibenzylammonium (DBA)/methyl triazolium (MTA) stations on the thread and anthracene/triisopropylsilyl-acetylene stoppers, respectively. In the protonated rotaxane, the macrocycle primarily resides on the DBA station, followed by directional shuttling to the MTA station upon treatment with base. Addition of fluoride as an additional chemical input cleaves the triisopropylsilyl stopper, leading to release of the macrocycle and the half-thread into solution. The released macrocycle can be recaptured by protonation, and the mechanical bond can be reestablished via CuAAC click reaction, enabled by the terminal acetylene unit on the half-thread. This generates an elongated second-generation rotaxane transporter, which was used for a second cycle of directional macrocycle transport and release, proving the possibility of an iterative operation of the rotaxane-transporter in this molecular design.
Source: Chemistry - A European Journal
Institution: University of Duisburg-Essen
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Awards: G2808631332, G331363160, G51602788, G755880473
OpenAlex ID: W4409229647