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Self-Trapping of Excitons, Violation of Condon Approximation, and Efficient Fluorescence in Conjugated Cycloparaphenylenes

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† Theoretical Division, Center for Nonlinear Studies and Center for Integrated Nanotechnologies (CINT), Los Alamos National Laboratory, Los Alamos, New Mexico 87545, United States
‡ Department of Electrical and Computer Engineering, and Photonics Center, Boston University, Boston, Massachusetts 02215, United States
§ Universidad Nacional de Quilmes, Roque Saenz Pea 352, B1876BXD Bernal, Argentina
∥ Department of Chemistry and Biochemistry and Materials Science Institute 1253, University of Oregon, Eugene, Oregon 97403, United States
*E-mail: [email protected]
Cite this: Nano Lett. 2014, 14, 11, 6539–6546
Publication Date (Web):October 13, 2014
https://doi.org/10.1021/nl503133e
Copyright © 2014 American Chemical Society
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    Abstract

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    Cycloparaphenylenes, the simplest structural unit of armchair carbon nanotubes, have unique optoelectronic properties counterintuitive in the class of conjugated organic materials. Our time-dependent density functional theory study and excited state dynamics simulations of cycloparaphenylene chromophores provide a simple and conceptually appealing physical picture explaining experimentally observed trends in optical properties in this family of molecules. Fully delocalized degenerate second and third excitonic states define linear absorption spectra. Self-trapping of the lowest excitonic state due to electron–phonon coupling leads to the formation of spatially localized excitation in large cycloparaphenylenes within 100 fs. This invalidates the commonly used Condon approximation and breaks optical selection rules, making these materials superior fluorophores. This process does not occur in the small molecules, which remain inefficient emitters. A complex interplay of symmetry, π-conjugation, conformational distortion and bending strain controls all photophysics of cycloparaphenylenes.

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    Additional computational results and plots of natural transition orbitals for excited states. This material is available free of charge via the Internet at http://pubs.acs.org.

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