Issue 46, 2019

The butterfly effect in bisfluorenylidene-based dihydroacenes: aggregation induced emission and spin switching

Abstract

Linear acenes are a well-studied class of polycyclic aromatic hydrocarbons and their established physical properties have led to their widespread application across the field of organic electronics. However, their quinoidal forms – dihydroacenes – are much less explored and exhibit vastly different photophysical and electronic properties due to their non-planar, cross-conjugated nature. In this work, we present a series of difluorenylidene dihydroacenes which exhibit a butterfly-like structure with a quinoidal skeleton, resulting in comparatively higher optical gaps and lower redox activities than those of their planar analogs. We found that these compounds exhibit aggregation induced emission (AIE), activated through restriction of the “flapping” vibrational mode of the molecules in the solid state. Furthermore, anthracene-containing dihydroacenes exhibit thermally activated ground-state spin switching as evidenced by planarization of the acene core and diradical activity recorded by EPR. These two characteristics in this relatively unexplored class of materials provide new insights for the design of multifunctional materials.

Graphical abstract: The butterfly effect in bisfluorenylidene-based dihydroacenes: aggregation induced emission and spin switching

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Aga 2019
Accepted
04 Okt 2019
First published
07 Okt 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 10733-10739

The butterfly effect in bisfluorenylidene-based dihydroacenes: aggregation induced emission and spin switching

X. Yin, J. Z. Low, K. J. Fallon, D. W. Paley and L. M. Campos, Chem. Sci., 2019, 10, 10733 DOI: 10.1039/C9SC04096J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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