A Terrylene Bisimide based Universal Host for Aromatic Guests to Derive Contact Surface-Dependent Dispersion Energies.
- Resource Type
- Academic Journal
- Authors
- 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.
- Source
- Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: PubMed not MEDLINE; MEDLINE
- Subject
- Language
- English
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.)