Donor-functionalized polydentate pyrylium salts and phosphinines: synthesis, structural characterization, and photophysical properties

C. Müller, D. Wasserberg, J.J.M. Weemers, E.A. Pidko, S. Hoffmann, M. Lutz, A.L. Spek, S.C.J. Meskers, R.A.J. Janssen, R.A. Santen, van, D. Vogt

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Abstract

A series of donor-functionalized pyrylium salts have been prepd. by classical condensation reactions which were further converted into the corresponding thienyl- and pyridyl-substituted polydentate l3-phosphinines by reaction with P(SiMe3)3. Further chem. modification of these phosphorus heterocycles with Hg(OAc)2 in the presence of methanol resulted in the formation of l5-phosphinines. The photophys. properties of a selected series of thienyl- and pyridyl-functionalized pyrylium salts, l3- and l5-phosphinines, were investigated and the results compared and supported by theor. calcns. on the DFT level. Significant fluorescence was obsd. for the pyrylium salts and l5-phosphinines. In contrast, the heteroarom. substituted l3-phosphinines show very little emission which is consistent with the low oscillator strength predicted by DFT calcns. for this p-p* transition. Furthermore, all three classes of compds. show readily observable phosphorescence in soln., which was detd. by time-gated detection at low temp. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)4548-4559
JournalChemistry : A European Journal
Volume13
Issue number16
DOIs
Publication statusPublished - 2007

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