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

Chemical Science
Xiaodong YinLuis M Campos

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.

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Citations

Aug 1, 2020·Advanced Materials·Haoke ZhangBen Zhong Tang
Jul 15, 2020·Angewandte Chemie·Christian SaalfrankHolger Braunschweig
Sep 24, 2020·Chemical Communications : Chem Comm·Vicente G JiménezAraceli G Campaña
Jul 16, 2020·Chemistry : a European Journal·Antonio Sánchez-RuizJoaquin C Garcia Martinez
Jan 27, 2021·Chemical Communications : Chem Comm·Yaorong ChenWenjing Hong
Mar 31, 2021·Chemistry : a European Journal·Qin XiangZhe Sun
Jul 14, 2021·Chemical Communications : Chem Comm·Brian P CorbetBen L Feringa
Nov 27, 2019·The Journal of Organic Chemistry·Tomohiko NishiuchiTakashi Kubo
Sep 20, 2020·Journal of the American Chemical Society·Airi KawamuraJohn S Anderson
Oct 26, 2021·Journal of the American Chemical Society·Marco B S WoninkBen L Feringa
Oct 31, 2021·Nature Communications·Yi ShenJuan Casado

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Methods Mentioned

BETA
electron paramagnetic resonance
NMR

Software Mentioned

ONIOM

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