Primary phosphines (RPH2) are an underdeveloped class of ligand1 due to their hazardous reputation as volatile and toxic compounds that can spontaneously combust in air; however the highly reactive P-H bonds can be easily functionalised to give useful derivatives with a wide variety of applications. Recently the Higham research group has discovered a number of primary phosphines with unprecedented air-stability, which is credited to electronic effects.2Here we report the original3 and improved synthesis of the first air-stable fluorescent primary phosphines which are based on the well-known fluorophore BODIPY, containing a p-conjugated backbone. The improved synthesis has also been successfully scaled-up to 15 grams whilst retaining good yields. BODIPY was the fluorophore chosen as it has been extensively studied and its related compounds have high fluorescence quantum yields, high thermal and photochemical stability and chemical robustness.4There has been relatively little research on the coordination chemistry of primary phosphines, here we report the coordination of group 6, 8 and 11 transition metals to the BODIPY primary phosphines and the effect the metals have on the photophysical properties of the complexes.1 M. Brynda, Coord. Chem. Rev., 2005  , 249, 2013-2034.2 B. Stewart, A. Harriman and L. J. Higham, Organometallics, 2011  , 30, 5338-5343.3 L. H. Davies, B. Stewart R. W. Harrington, W. Clegg and L. J. Higham, Angew. Chem. Int. Ed., 2012  , 51, 4921-4924.4 G. Ulrich, R. Ziessel and A. Harriman, Angew. Chem. Int. Ed., 2008  , 47, 1184-1201.

Highly fluorescent phosphines based on the BODIPY scaffold

247th National Meeting (2014)

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