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Experimental and Computational Study of BODIPY Dye-Labeled Cavitand Dynamics

Pochorovski, Igor and Knehans, Tim and Nettels, Daniel and Müller, Astrid M. and Schweizer, W. Bern and Caflisch, Amedeo and Schuler, Benjamin and Diederich, François (2014) Experimental and Computational Study of BODIPY Dye-Labeled Cavitand Dynamics. Journal of the American Chemical Society, 136 (6). pp. 2441-2449. ISSN 0002-7863. doi:10.1021/ja4104292.

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Understanding the distance distribution and dynamics between moieties attached to the walls of a resorcin[4]arene cavitand, which is switchable between an expanded kite and a contracted vase form, might enable the use of this molecular system for the study of fundamental distance-dependent interactions. Toward this goal, a combined experimental and molecular dynamics (MD) simulation study on donor/acceptor borondipyrromethene (BODIPY) dye-labeled cavitands present in the vase and kite forms was performed. Direct comparison between anisotropy decays calculated from MD simulations with experimental fluorescence anisotropy data showed excellent agreement, indicating that the simulations provide an accurate representation of the dynamics of the system. Distance distributions between the BODIPY dyes were established by comparing time-resolved Förster resonance energy transfer experiments and MD simulations. Fluorescence intensity decay curves emulated on the basis of the MD trajectories showed good agreement with the experimental data, suggesting that the simulations present an accurate picture of the distance distributions and dynamics in this molecular system and provide an important tool for understanding the behavior of extended molecular systems and designing future applications.

Item Type:Article
Related URLs:
URLURL TypeDescription
Müller, Astrid M.0000-0002-2785-6808
Diederich, François0000-0003-1947-6327
Additional Information:© 2014 American Chemical Society. Received: October 16, 2013. Publication Date (Web): February 3, 2014. This work was supported by grants from the Swiss National Science Foundation (SNF). I.P. acknowledges the receipt of a fellowship from the Fonds der Chemischen Industrie. Research was partly carried out in the Laser Resource Center of the Beckman Institute of the California Institute of Technology and supported by the Arnold and Mabel Beckman Foundation. We thank Prof. Dr. Gunnar Jeschke, Dr. Marc-Olivier Ebert, and Dr. Andreas Vitalis for helpful discussions, Dimitry Kotlyar for help with the Table of Contents artwork, and Dr. Kenno Vanommeslaeghe for providing parametrization of the cavitands via the Paramchem engine.
Funding AgencyGrant Number
Swiss National Science Foundation (SNF)UNSPECIFIED
Fonds der Chemischen IndustrieUNSPECIFIED
Arnold and Mabel Beckman FoundationUNSPECIFIED
Issue or Number:6
Record Number:CaltechAUTHORS:20140326-103649578
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Official Citation:Experimental and Computational Study of BODIPY Dye-Labeled Cavitand Dynamics Igor Pochorovski, Tim Knehans, Daniel Nettels, Astrid M. Müller, W. Bernd Schweizer, Amedeo Caflisch, Benjamin Schuler, and François Diederich Journal of the American Chemical Society 2014 136 (6), 2441-2449
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:44527
Deposited By: Ruth Sustaita
Deposited On:26 Mar 2014 19:31
Last Modified:10 Nov 2021 16:53

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