Home > Publications database > A Terrylene Bisimide based Universal Host for Aromatic Guests to Derive Contact Surface‐Dependent Dispersion Energies > print

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005     20250723171752.0
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082 _ _ |a 540
100 1 _ |a Rühe, Jessica
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245 _ _ |a A Terrylene Bisimide based Universal Host for Aromatic Guests to Derive Contact Surface‐Dependent Dispersion Energies
260 _ _ |a Weinheim
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520 _ _ |a $π–π$ 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.
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700 1 _ |a Rajeevan, Megha
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700 1 _ |a Shoyama, Kazutaka
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700 1 _ |a Swathi, Rotti Srinivasamurthy
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700 1 _ |a Wuerthner, Frank
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773 1 8 |a 10.1002/anie.202318451
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773 _ _ |a 10.1002/anie.202318451
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|u Deposition Numbers 2310187 (forTBI-C) and 2310188 (for diindenoperylene⊂TBI-C) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service.
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|u In our calculation we have assumed that the π-surfaces of both TBIs are in close contact to the guest and accordingly contribute to the measured binding constant. Because this might not be the case i.e. due to not perfect distance the calculated value forσis accordingly a lower limit.
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