Diphosphahexaarenes as Highly Fluorescent and Stable Materials

Oligoarenes are regarded as subunits of π‐extended carbon nanoforms, such as graphene and nanotubes, with exceptional technological importance. Fused arenes can thus provide fundamental insight into the nature of the electronic properties of fused polyaromatic rings and pave the way for the design o...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-11, Vol.57 (46), p.15157-15161
Main Authors: Hindenberg, Philip, Busch, Marvin, Paul, Alexander, Bernhardt, Moritz, Gemessy, Patrick, Rominger, Frank, Romero‐Nieto, Carlos
Format: Article
Language:English
Subjects:
Aromatic compounds
Crystal structure
Crystallography
DFT calculations
electrochemistry
Embedding
Fluorescence
Graphene
Molecular structure
Nanotechnology
Nanotubes
Optoelectronics
Phosphorus
phosphorus heterocycles
photophysical properties
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Summary:Oligoarenes are regarded as subunits of π‐extended carbon nanoforms, such as graphene and nanotubes, with exceptional technological importance. Fused arenes can thus provide fundamental insight into the nature of the electronic properties of fused polyaromatic rings and pave the way for the design of extended graphene‐like materials. However, large π‐extended arenes often show low stability. Herein we report the straightforward preparation of linearly fused diphosphahexaarenes containing two six‐membered phosphorus heterocycles. They are highly stable towards air, water, and light over months in both solution and the solid state. Single‐crystal X‐ray crystallography confirmed the molecular structure of all derivatives. Investigations of their optoelectronic properties revealed that the diphosphahexaarenes exhibit ambipolar redox behavior and high fluorescence quantum yields. Embedding six‐membered phosphorus rings into large acenes thus opens up new opportunities for the investigation of polyaromatic systems. Two P rings in a line: The straightforward preparation of linearly fused systems containing two six‐membered phosphorus heterocycles, diphosphahexaarenes, is presented (see structures). They are very stable towards air, moisture and light. Optoelectronic investigations revealed ambipolar redox behavior for all derivatives and high fluorescence quantum yields up to 0.85.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201809754