Diphosphahexaarenes as Highly Fluorescent and Stable Materials. Issue 46 (24th October 2018)

• Record Type: Journal Article
• Authors: Hindenberg, Philip; Busch, Marvin; Paul, Alexander; Bernhardt, Moritz; Gemessy, Patrick; Rominger, Frank; Romero‐Nieto, Carlos
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 46(2018)
• Page Start: 15157
• Page End: 15161
• Publication Date: 2018-10-24
• Subjects: DFT calculations -- electrochemistry -- fluorescence -- phosphorus heterocycles -- photophysical properties; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201809754
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : 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.