Glycoluril-tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests.
作者： Yoann Cotelle , Marie Hardouin-Lerouge , Stéphanie Legoupy , Olivier Alévêque , Eric Levillain
DOI: 10.3762/BJOC.11.115
关键词:
摘要: Glycoluril-based molecular clips incorporating tetrathiafulvalene (TTF) sidewalls have been synthesized through different strategies with the aim of investigating effect electrochemical and spatial properties for binding neutral accepting guests. We in particular focused our study on spacer extension order to tune intramolecular TTF···TTF distance within clip and, consequently, redox behavior receptor. Carried out at concentrations solution, spectroelectrochemical experiments provide evidence mixed-valence and/or π-dimer intermolecular interactions between TTF units from two closed clips. The stepwise oxidation each involves an mechanism three one-electron processes charge-coupled chemical reactions, a scheme which is supported by simulations. fine-tunable π-donating ability cavity size allow control interaction towards strong electron acceptor such as tetrafluorotetracyanoquinodimethane (F4-TCNQ) or weaker 1,3-dinitrobenzene (m-DNB).
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