Abstract
Pyrazoline and its derivatives often exhibit strong emissions in dilute solutions, but their emission intensity is often dramatically reduced in the solid state due to strong intermolecular interactions between neighboring molecules. In this report, we successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline (PPDPD), into which seven fluorine (F) atoms were incorporated. In the solid state, PPDPD emits a strong blue light at λmax 430 nm with a fluorescence quantum yield of up to 41.3%. Single-crystal analysis showed the presence of intra/intermolecular C-H···F bonds that may impede molecular motion and block the non-radiative decay channel. Compound PPDPD therefore shows high emission efficiency in the solid state.
Highlights
Amongst the numerous heterocyclic organic luminescent materials, pyrazoline and its derivatives have received increasing attention due to their excellent electro-optical properties [1–14] and wide range of applications
In order to overcome these problems, Gu and co-workers introduced a single aggregation-induced emission (AIE) unit based on a pyrazoline backbone into the polymer chain via atom-transfer radical polymerization [25]
To the best of our knowledge, most of the current research in this area is focused on AIE-terminated or AIE polymers; small molecules based on a pyrazoline backbone have not been fully investigated [26,27]
Summary
Amongst the numerous heterocyclic organic luminescent materials, pyrazoline and its derivatives have received increasing attention due to their excellent electro-optical properties [1–14] and wide range of applications. They are used in fluorescent probes, organic light-emitting diodes, and many other materials [15–24]. We successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline (PPDPD, Scheme 1), into which seven fluorines (F) were incorporated. We successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline We believe that the intermolecular interactions between neighboring molecules of the PPDPD compound may differ from those present in commonly-used commonly-used pyrazoline pyrazolineand andits its derivatives derivativesdue dueto tothe theinfluence influenceof ofthe theC-H.
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