Nine organotin fluorocarboxylates R n SnO 2 CR f (n = 3, R = Bu, R f = CF 3 , C 2 F 5 , C 3 F 7 , C 7 F 15 ; R = Et, R f = CF 3 , C 2 F 5 ; R = Me, R f = C 2 F 5 ; n = 2, R = Me, R f = CF 3 ) have been synthesized; key examples have been used to deposit fluorine-doped SnO 2 thin films by atmospheric pressure chemical vapour deposition. Et 3 SnO 2 CC 2 F 5 , in particular, gives high-quality films with fast deposition rates despite adopting a polymeric, carboxylate-bridged structure in the solid state, as determined by X-ray crystallography. Gas-phase electron diffraction on the model compound Me 3 SnO 2 CC 2 F 5 shows that accessible conformations do not allow contact between tin and fluorine, and that direct transfer is therefore unlikely to be part of the mechanism for fluorine incorporation in SnO 2 films. The structure of Me 2 Sn(O 2 CCF 3 ) 2 (H 2 O) has also been determined and adopts a trans-Me 2 SnO 3 coordination sphere about tin in which each carboxylate group is monodentate.
Perfluoroalkytin compounds R (4−n) Sn(R f ) n (R = Me, Et, Bu, R f = C 4 F 9 , n = 1; R = Bu, R f = C 4 F 9 , n = 2, 3; R = Bu, R f = C 6 F 13 , n = 1) have been synthesized, characterized by 1 H, 13 C, 19 F and 119 Sn NMR, and evaluated as precursors for the atmospheric pressure chemical vapour deposition of fluorine-doped SnO 2 thin films. All precursors were sufficiently volatile in the range 84-136 • C and glass substrate temperatures of ca 550 • C to yield high-quality films with ca 0.79-2.02% fluorine incorporation, save for Bu 3 SnC 6 F 13 , which incorporated <0.05% fluorine. Films were characterized by X-ray diffraction, scanning electron microscopy, thickness, haze, emissivity, and sheet resistance. The fastest growth rates and highest quality films were obtained from Et 3 SnC 4 F 9 . An electron diffraction study of Me 3 SnC 4 F 9 revealed four conformations, of which only the two of lowest abundance showed close F· · · Sn contacts that could plausibly be associated with halogen transfer to tin, and in each case it was fluorine attached to either the γ -or δ-carbon atoms of the R f chain.
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