A Terrylene Bisimide based Universal Host for Aromatic Guests to Derive Contact Surface-Dependent Dispersion Energies.

Autor: Rühe J; Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany., Rajeevan M; School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram, 695551, India., Shoyama K; Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.; Center for Nanosystems Chemistry (CNC), Universität Würzburg, Theodor-Boveri-Weg, 97074, Würzburg, Germany., Swathi RS; School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram, 695551, India., Würthner F; Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.; Center for Nanosystems Chemistry (CNC), Universität Würzburg, Theodor-Boveri-Weg, 97074, Würzburg, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Apr 22; Vol. 63 (17), pp. e202318451. Date of Electronic Publication: 2024 Mar 18.
DOI: 10.1002/anie.202318451
Abstrakt: π-π interactions are among the most important intermolecular interactions in supramolecular systems. Here we determine experimentally a universal parameter for their strength that is simply based on the size of the interacting contact surfaces. Toward this goal we designed a new cyclophane based on terrylene bisimide (TBI) π-walls connected by para-xylylene spacer units. With its extended π-surface this cyclophane proved to be an excellent and universal host for the complexation of π-conjugated guests, including small and large polycyclic aromatic hydrocarbons (PAHs) as well as dye molecules. The observed binding constants range up to 10 8  M -1 and show a linear dependence on the 2D area size of the guest molecules. This correlation can be used for the prediction of binding constants and for the design of new host-guest systems based on the herewith derived universal Gibbs interaction energy parameter of 0.31 kJ/molÅ 2 in chloroform.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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