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Excited-State Aromatic Interactions in the Aggregation-Induced Emission of Molecular Rotors

Sturala, Jiri; Etherington, Marc K.; Bismillah, Aisha N; Higginbotham, Heather F.; Trewby, William J.; Aguilar, Juan A.; Bromley, Elizabeth H.C.; Avestro, Alyssa-Jennifer; Monkman, Andrew P.; McGonigal, Paul R.

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Authors

Jiri Sturala

Marc K. Etherington

Aisha N Bismillah

Heather F. Higginbotham

William J. Trewby

Andrew P. Monkman



Abstract

Small, apolar aromatic groups, such as phenyl rings, are commonly included in the structures of fluorophores in order to impart hindered intramolecular rotations, leading to desirable solid-state luminescence properties. However, they are not normally considered to take part in through-space interactions that influence the fluorescent output. Here, we report on the photoluminescence properties of a series of phenyl-ring molecular rotors bearing three, five, six, and seven phenyl groups. The fluorescent emissions from two of the rotors are found to originate, not from the localized excited state as one might ex-pect, but from unanticipated through-space aromatic dimer states. We demonstrate that these relaxed dimer states can form as a result of intra- or intermolecular interactions across a range of environments in solution and solid samples, including conditions that promote aggregation-induced emission. Computational modeling also suggests that the formation of aro-matic-dimer excited states may account for the photophysical properties of a previously reported luminogen. These results imply, therefore, that this is a general phenomenon that should be taken into account when designing and interpreting the fluorescent outputs of luminescent probes and optoelectronic devices based on fluorescent molecular rotors.

Journal Article Type Article
Acceptance Date Nov 18, 2017
Online Publication Date Nov 18, 2017
Publication Date Nov 18, 2017
Deposit Date Nov 20, 2017
Publicly Available Date Nov 20, 2017
Journal Journal of the American Chemical Society
Print ISSN 0002-7863
Electronic ISSN 1520-5126
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 139
Issue 49
Pages 17882-17889
DOI https://doi.org/10.1021/jacs.7b08570
Public URL https://durham-repository.worktribe.com/output/1370980

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Copyright Statement
This is an open access article published under a Creative Commons Attribution (CC-BY)
License, which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.






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